CAS: 84573-16-0; (1R,2R,3S,3Ar,8Bs)-1,8B-Dihydroxy-6,8-Dimethoxy-3A-(4-Methoxyphenyl)-N,N-Dimethyl-3-Phenyl-2,3,3A,8B-Tetrahydro-1H-Cyclopenta[b]Benzofuran-2-Carboxamide

该化合物是一种复杂的有机化合物,其特点是其多环结构,包括环球[b]苯丙酸核心.这种化合物具有多种功能组的特点,包括氢氧基(-OH),甲基氧(-OCH3)和氨基(-CON(CH3)2),有助于其潜在的生物活动.国际化合联的名称所显示的立体化学化学结构安排表明,这些原子可能影响化合物与生物目标的相互作用.这种化合物经常因其药理特性而研究其潜在治疗作用,包括潜在的影响.这种混合和联组的存在具有多种功能特性,这种特性可能提高整个生物化学特性,从而影响整个化学特性.

结构式图片

物理性质

MSDS等安全信息

上下游产品

(2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide dimethyl amine endo r°Caglic acid N,N-dimethylammonium chloride

合成工艺路线路线简述

  • 1139257-91-2 = 84573-16-0
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt1.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    1139257-91-2 = 84573-16-0
    反应条件:1.1 Reagents: Methanaminium,N,N,N-Trimethyl-,(T-4)-Tris(Acetato-Ko)Hydroborate(1-) (1:1) Solvents: Acetic Acid,Acetonitrile
    标题:Tetramethylammonium Triacetoxyborohydride
    作者:Houri,Ahmad F.; Et Al
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001 卷标:1 页码:1-3]

    132463-96-8 = 84573-16-0
    反应条件:1.1 Reagents: 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone Solvents: Tetrahydrofuran2.1 -
    标题:An Unusual Oxidative Cyclization. A Synthesis And Absolute Stereochemical Assignment Of (-)-Rocaglamide
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:1990 卷标:112(24) 页码:9022-4]

    1699754-34-1 = 84573-16-0
    反应条件:1.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C1.2 Reagents: Sodium Thiosulfate Solvents: Water2.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt2.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    901774-46-7 = 84573-16-0
    反应条件:1.1 Reagents: Acetic Acid,Methanaminium,N,N,N-Trimethyl-,(T-4)-Tris(Acetato-Ko)Hydroborate(1-) (1:1) Solvents: Acetonitrile; 3 H,Rt1.2 Reagents: Potassium Sodium Tartrate Solvents: Water; 30 Min,Rt2.1 Reagents: Potassium Hydroxide Solvents: Methanol; 12 H,44 °C2.2 Reagents: Hydrochloric Acid Solvents: Water3.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; Rt -> 0 °C3.2 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride; 5 Min,0 °C; 30 Min,0 °C3.3 Reagents: Triethylamine; 1 H,0 °C; 12 H,Rt3.4 Reagents: Hydrochloric Acid Solvents: Water; Rt
    标题:Enantioselective Photocycloaddition Mediated By Chiral Bronsted Acids: Asymmetric Synthesis Of The Rocaglamides
    作者:Gerard,Baudouin; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(24) 页码:7754-7755]

    = 84573-16-0
    反应条件:1.1 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C2.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C2.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C2.4 Reagents: Ammonium Chloride Solvents: Water2.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 53.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux4.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt4.2 Reagents: Ammonium Chloride Solvents: Water; Rt5.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C5.2 Reagents: Sodium Thiosulfate Solvents: Water6.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt6.2 Solvents: Acetonitrile; 20 H,Rt6.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    = 84573-16-0
    反应条件:1.1 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt2.1 Reagents: Butyllithium Solvents: Hydrofluoric Acid; -78 °C; 1 H,-78 °C2.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); 1 H,-78 °C2.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C2.4 Reagents: Ammonium Chloride Solvents: Water2.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 53.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux; Reflux -> Rt4.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt4.2 Reagents: Ammonium Chloride Solvents: Water5.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C5.2 Reagents: Sodium Thiosulfate Solvents: Water6.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt6.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    1699754-28-3 = 84573-16-0
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt2.1 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C3.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C3.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C3.4 Reagents: Ammonium Chloride Solvents: Water3.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 54.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux5.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt5.2 Reagents: Ammonium Chloride Solvents: Water; Rt6.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C6.2 Reagents: Sodium Thiosulfate Solvents: Water7.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt7.2 Solvents: Acetonitrile; 20 H,Rt7.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    = 84573-16-0
    反应条件:1.1 Reagents: 1,1,1,3,3,3-Hexafluoro-2-Propanol,Bis(Trifluoroacetoxy)Iodobenzene Solvents: Allyl Alcohol; -10 °C -> Rt; 2 H,Rt2.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 30 Min,0 °C3.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt3.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt3.3 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt4.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C4.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C4.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C4.4 Reagents: Ammonium Chloride Solvents: Water4.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 55.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux6.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt6.2 Reagents: Ammonium Chloride Solvents: Water; Rt7.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C7.2 Reagents: Sodium Thiosulfate Solvents: Water8.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt8.2 Solvents: Acetonitrile; 20 H,Rt8.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    1139257-91-2 = 84573-16-0
    反应条件:1.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt1.2 Solvents: Acetonitrile; 20 H,Rt1.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    506-59-2 + 190385-15-0 = 84573-16-0
    反应条件:1.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; Rt -> 0 °C1.2 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride; 5 Min,0 °C; 30 Min,0 °C1.3 Reagents: Triethylamine; 1 H,0 °C; 12 H,Rt1.4 Reagents: Hydrochloric Acid Solvents: Water; Rt
    标题:Enantioselective Photocycloaddition Mediated By Chiral Bronsted Acids: Asymmetric Synthesis Of The Rocaglamides
    作者:Gerard,Baudouin; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(24) 页码:7754-7755]

    132463-97-9 = 84573-16-0 [标题:Reaction Conditions
    标题:An Unusual Oxidative Cyclization. A Synthesis And Absolute Stereochemical Assignment Of (-)-Rocaglamide
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:1990 卷标:112(24) 页码:9022-4]

    143901-35-3 = 84573-16-0
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Methanol; 12 H,44 °C1.2 Reagents: Hydrochloric Acid Solvents: Water2.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; Rt -> 0 °C2.2 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride; 5 Min,0 °C; 30 Min,0 °C2.3 Reagents: Triethylamine; 1 H,0 °C; 12 H,Rt2.4 Reagents: Hydrochloric Acid Solvents: Water; Rt
    标题:Enantioselective Photocycloaddition Mediated By Chiral Bronsted Acids: Asymmetric Synthesis Of The Rocaglamides
    作者:Gerard,Baudouin; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(24) 页码:7754-7755]

    1699754-34-1 = 84573-16-0
    反应条件:1.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C1.2 Reagents: Sodium Thiosulfate Solvents: Water2.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt2.2 Solvents: Acetonitrile; 20 H,Rt2.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    1699754-33-0 = 84573-16-0
    反应条件:1.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Rt2.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C2.2 Reagents: Sodium Thiosulfate Solvents: Water3.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt3.2 Solvents: Acetonitrile; 20 H,Rt3.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    1699754-33-0 = 84573-16-0
    反应条件:1.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt1.2 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C2.2 Reagents: Sodium Thiosulfate Solvents: Water3.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt3.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    1699754-32-9 = 84573-16-0
    反应条件:1.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux2.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt2.2 Reagents: Ammonium Chloride Solvents: Water; Rt3.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C3.2 Reagents: Sodium Thiosulfate Solvents: Water4.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt4.2 Solvents: Acetonitrile; 20 H,Rt4.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    1699754-32-9 = 84573-16-0
    反应条件:1.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux; Reflux -> Rt2.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt2.2 Reagents: Ammonium Chloride Solvents: Water3.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C3.2 Reagents: Sodium Thiosulfate Solvents: Water4.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt4.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    901774-42-3 = 84573-16-0
    反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol; Rt; 20 Min,60 °C1.2 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: Acetic Acid,Methanaminium,N,N,N-Trimethyl-,(T-4)-Tris(Acetato-Ko)Hydroborate(1-) (1:1) Solvents: Acetonitrile; 3 H,Rt2.2 Reagents: Potassium Sodium Tartrate Solvents: Water; 30 Min,Rt3.1 Reagents: Potassium Hydroxide Solvents: Methanol; 12 H,44 °C3.2 Reagents: Hydrochloric Acid Solvents: Water4.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; Rt -> 0 °C4.2 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride; 5 Min,0 °C; 30 Min,0 °C4.3 Reagents: Triethylamine; 1 H,0 °C; 12 H,Rt4.4 Reagents: Hydrochloric Acid Solvents: Water; Rt
    标题:Enantioselective Photocycloaddition Mediated By Chiral Bronsted Acids: Asymmetric Synthesis Of The Rocaglamides
    作者:Gerard,Baudouin; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(24) 页码:7754-7755]

    1754-62-7 + 1098-92-6 = 84573-16-0
    反应条件:1.1 Reagents: (4R,5R)-α4,α4,α5,α5-Tetra-9-Phenanthrenyl-2,2-Diphenyl-1,3-Dioxolane-4,5-Dimetha... Solvents: Dichloromethane,Toluene; 5 Min; 12 H,-70 °C1.2 Solvents: Methanol2.1 Reagents: Sodium Methoxide Solvents: Methanol; Rt; 20 Min,60 °C2.2 Reagents: Ammonium Chloride Solvents: Water3.1 Reagents: Acetic Acid,Methanaminium,N,N,N-Trimethyl-,(T-4)-Tris(Acetato-Ko)Hydroborate(1-) (1:1) Solvents: Acetonitrile; 3 H,Rt3.2 Reagents: Potassium Sodium Tartrate Solvents: Water; 30 Min,Rt4.1 Reagents: Potassium Hydroxide Solvents: Methanol; 12 H,44 °C4.2 Reagents: Hydrochloric Acid Solvents: Water5.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; Rt -> 0 °C5.2 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride; 5 Min,0 °C; 30 Min,0 °C5.3 Reagents: Triethylamine; 1 H,0 °C; 12 H,Rt5.4 Reagents: Hydrochloric Acid Solvents: Water; Rt
    标题:Enantioselective Photocycloaddition Mediated By Chiral Bronsted Acids: Asymmetric Synthesis Of The Rocaglamides
    作者:Gerard,Baudouin; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(24) 页码:7754-7755]

    1699754-29-4 + 52189-63-6 = 84573-16-0
    反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C1.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C1.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C1.4 Reagents: Ammonium Chloride Solvents: Water1.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 52.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux3.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt3.2 Reagents: Ammonium Chloride Solvents: Water; Rt4.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C4.2 Reagents: Sodium Thiosulfate Solvents: Water5.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt5.2 Solvents: Acetonitrile; 20 H,Rt5.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    1699754-29-4 + 52189-63-6 = 84573-16-0
    反应条件:1.1 Reagents: Butyllithium Solvents: Hydrofluoric Acid; -78 °C; 1 H,-78 °C1.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); 1 H,-78 °C1.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C1.4 Reagents: Ammonium Chloride Solvents: Water1.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 52.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux; Reflux -> Rt3.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt3.2 Reagents: Ammonium Chloride Solvents: Water4.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C4.2 Reagents: Sodium Thiosulfate Solvents: Water5.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt5.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    1699754-28-3 = 84573-16-0
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt1.3 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C2.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C2.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C2.4 Reagents: Ammonium Chloride Solvents: Water2.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 53.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux4.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt4.2 Reagents: Ammonium Chloride Solvents: Water; Rt5.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C5.2 Reagents: Sodium Thiosulfate Solvents: Water6.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt6.2 Solvents: Acetonitrile; 20 H,Rt6.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    1699754-28-3 = 84573-16-0
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified1.3 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt2.1 Reagents: Butyllithium Solvents: Hydrofluoric Acid; -78 °C; 1 H,-78 °C2.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); 1 H,-78 °C2.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C2.4 Reagents: Ammonium Chloride Solvents: Water2.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 53.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux; Reflux -> Rt4.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt4.2 Reagents: Ammonium Chloride Solvents: Water5.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C5.2 Reagents: Sodium Thiosulfate Solvents: Water6.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt6.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    14874-70-5 + 43625-65-6 = 84573-16-0
    反应条件:1.1 Reagents: 1,1,1,3,3,3-Hexafluoro-2-Propanol,Bis(Trifluoroacetoxy)Iodobenzene Solvents: Allyl Alcohol; -10 °C -> Rt; 2 H,Rt1.2 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 30 Min,0 °C2.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt2.3 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C3.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C3.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C3.4 Reagents: Ammonium Chloride Solvents: Water3.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 54.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux5.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt5.2 Reagents: Ammonium Chloride Solvents: Water; Rt6.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C6.2 Reagents: Sodium Thiosulfate Solvents: Water7.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt7.2 Solvents: Acetonitrile; 20 H,Rt7.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936]

    14874-70-5 + 43625-65-6 = 84573-16-0
    反应条件:1.1 Reagents: Bis(Trifluoroacetoxy)Iodobenzene Solvents: Allyl Alcohol,1,1,1,3,3,3-Hexafluoro-2-Propanol; -10 °C; -10 °C -> Rt; 2 H,Rt1.2 Reagents: Diisopropylethylamine Solvents: Dichloromethane; Rt -> 0 °C; 30 Min,0 °C2.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified2.3 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt3.1 Reagents: Butyllithium Solvents: Hydrofluoric Acid; -78 °C; 1 H,-78 °C3.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); 1 H,-78 °C3.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C3.4 Reagents: Ammonium Chloride Solvents: Water3.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 54.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux; Reflux -> Rt5.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt5.2 Reagents: Ammonium Chloride Solvents: Water6.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C6.2 Reagents: Sodium Thiosulfate Solvents: Water7.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt7.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    1699754-28-3 = 84573-16-0
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified2.1 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt3.1 Reagents: Butyllithium Solvents: Hydrofluoric Acid; -78 °C; 1 H,-78 °C3.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); 1 H,-78 °C3.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C3.4 Reagents: Ammonium Chloride Solvents: Water3.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 54.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux; Reflux -> Rt5.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt5.2 Reagents: Ammonium Chloride Solvents: Water6.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,Rt -> 90 °C; 15 Min,90 °C6.2 Reagents: Sodium Thiosulfate Solvents: Water7.1 Reagents: Sodium Borohydride Solvents: Acetic Acid,Acetonitrile; 30 Min,Rt; 20 H,Rt7.2 Reagents: Sodium Chloride Solvents: Water
    标题:Synthesis Of Each Enantiomer Of Rocaglamide By Means Of A Palladium(0)-Catalyzed Nazarov-Type Cyclization
    作者:Zhou,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(20) 页码:6037-6040]

    14874-70-5 + 2008704-56-9 + 43625-65-6 = 84573-16-0
    反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 30 Min,0 °C2.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 4 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt2.3 Reagents: Triethylamine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dichloromethane,Tetrahydrofuran; 12 H,Rt3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; -78 °C; 1 H,-78 °C3.2 Reagents: Lanthanate(2-),Pentachloro-,Lithium (1:2); -78 °C; 1 H,-78 °C3.3 Solvents: Tetrahydrofuran; 45 Min,-78 °C -> -30 °C3.4 Reagents: Ammonium Chloride Solvents: Water3.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 54.1 Reagents: Acetic Acid,Selenium Dioxide Solvents: 1,4-Dioxane; 30 Min,Rt -> Reflux5.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 15 Min,Rt5.2 Reagents: Ammonium Chloride Solvents: Water; Rt6.1 Reagents: Magnesium Iodide Solvents: Diethyl Ether,Toluene; 15 Min,90 °C6.2 Reagents: Sodium Thiosulfate Solvents: Water7.1 Reagents: Acetic Acid,Sodium Borohydride; 30 Min,Rt7.2 Solvents: Acetonitrile; 20 H,Rt7.3 Reagents: Sodium Chloride Solvents: Water; Rt
    标题:The Evolution Of The Total Synthesis Of Rocaglamide
    作者:Zhou,Zhe; Et Al
    参考文献:Chemistry - A European Journal 日期:2016 卷标:22(44) 页码:15929-15936
📜1,3-二甲氧基-5-氟苯置于selenium(Iv) Oxide,Sodium Tetrahydroborate,正丁基锂,Potassium Tert-Butylate,溶剂黄146,Magnesium Iodide体系中,用 四氢呋喃,1,4-二氧六环,乙醚,正己烷,甲苯,乙腈 作为反应溶剂,化学反应 23.0H,反应生成 楝酰胺
参考文献:罗卡酰胺的全合成演变
标题:罗卡酰胺的全合成演变
摘要:复杂的氟拉格琳(-)-Rocaglamide具有一个有趣的三环骨架,具有五个连续的立体中心,并且还显示出强大的抗癌,抗炎和杀虫活性.此完整说明详细介绍了分别在我们实验室中开发的,利用布朗斯台德酸催化和不对称pd 0催化的nazarov化学方法制备(+/-)-和(-)-Rocaglamide的不同方法.成功的不对称合成揭示了无法预料的机械复杂性,需要调整我们的策略来克服意外的消旋过程,异常的可逆环裂解步骤和非常容易的三烷基甲硅烷基团迁移.
DOI:10.1002/chem.201603312

海关参考信息

专利信息


专利号:US-7816544-B2
优先权日:2004-03-23
标 题:Synthesis of rocaglamide natural products via photochemical generation of oxidopyrylium species
发明人：JONES II GUILFORD; GERARD BAUDOUIN; PORCO JR JOHN A
权利人:UNIV BOSTON
摘要:The present invention provides new strategies for the synthesis of compounds of the rocaglamide family and related natural products. In particular, the new biomimetic synthetic approach involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile. This approach can be used for the formation of adducts containing an aglain core structure. Methods for the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.

专利号:US-2008177093-A1
优先权日:2004-03-23
标题 :Synthesis of Rocaglamide Natural Products Via Photochemical Generation of Oxidopyrylium Species

专利号:WO-2005092876-A1
优先权日:2004-03-23
标 题 :Synthesis of rocaglamide natural products via photochemical generation of oxidopyrylium species

专利号:US-2011065786-A1
优先权日:2004-03-23
标题:Synthesis of rocaglamide natural products via photochemical generation of oxidopyrylium species

专利号:CA-2652873-A1
优先权日:2006-05-22
标题:Asymmetric synthesis of rocaglamides via enantioselective photocycloaddition mediated by chiral bronsted acids

专利号:US-8137509-B2
优先权日:2006-05-22
标题 :Asymmetric synthesis of rocaglamides via enantioselective photocycloaddition mediated by chiral brønsted acids

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主要参考文献


1: Rosenfeld P, Singh G, Paz Herrera A, Ji J, Seufzer B, Heng X, Boris-Lawrie K, Cochrane A. Putting a Kink in HIV-1 Particle Infectivity: Rocaglamide Inhibits HIV-1 Replication by Altering Gag-Genomic RNA Interaction. Viruses. 2024 Sep 23;16(9):1506. doi: 10.3390/v16091506.
2: Oblinger JL, Wang J, Wetherell GD, Agarwal G, Wilson TA, Benson NR, Fenger JM, Fuchs JR, Kinghorn AD, Chang LS. Anti-tumor effects of the eIF4A inhibitor didesmethylrocaglamide and its derivatives in human and canine osteosarcomas. Sci Rep. 2024 Aug 20;14(1):19349. doi: 10.1038/s41598-024-69171-3.
3: Oblinger J, Wang J, Wetherell G, Agarwal G, Wilson T, Benson N, Fenger J, Fuchs J, Kinghorn AD, Chang L. Anti-tumor Effects of the eIF4A Inhibitor Didesmethylrocaglamide and Its Derivatives in Human and Canine Osteosarcomas. Res Sq [Preprint]. 2024 Jun

合成参考文献


摘要:Bartels, F.; Zimmer, R.; Christmann, M., Science of Synthesis Knowledge Updates, (2017) 3, 297.
参考文献:10.1021/ja062621j
摘要:Gerard B, Sangji S, O'Leary DJ, Porco JA. Enantioselective photocycloaddition mediated by chiral Brønsted acids: asymmetric synthesis of the rocaglamides. J Am Chem Soc. 2006 Jun 21;128(24):7754–5. doi: 10.1021/ja062621j.
参考文献:10.1021/acs.accounts.0c00284
摘要:Frontier AJ, Hernandez JJ. New Twists in Nazarov Cyclization Chemistry. Acc Chem Res. 2020 Sep 15;53(9):1822–32. doi: 10.1021/acs.accounts.0c00284.
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