CAS: 85416-73-5; (S)-4-(3-(Cyclopentyloxy)-4-Methoxyphenyl)Pyrrolidin-2-One

该化合物是一种选择性磷化磷酸酯-4(PDE4)抑制剂,主要以其在治疗抑郁和炎症等条件下的潜在治疗用途而闻名,其特点是能够增加细胞内循环性亚丁基单磷酸(CAMP)含量,该含量在包括...

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CAS号1001860-35-0 (S)-methyl 3-(3... | CAS号137-43-9 溴代环戊烷 | CAS号67387-76-2 3-环戊氧-4-甲氧基苯甲醛 | CAS号621-59-0 异香兰素； 3-羟基-4-甲氧... | CAS号141099-44-7 methyl 3-cyano-...

合成工艺路线路线简述

  • 合成目标产物 S- (+)-Rolipram 主要起始原料 Ethanamine, N-[(3,5-Dichlorophenyl)Methylene]-2,2-Diethoxy-
  • 377073-84-2 = 85416-73-5
    反应条件:1.1 Reagents: Lithium Solvents: Ammonia
    标题:First Highly Regio- And Diastereoselective [3+2] Cycloaddition Of Chiral Nonracemic Fischer Carbene Complexes With Azomethine Ylides: An Enantioselective Synthesis Of (+)-Rolipram
    作者:Barluenga,Jose; Et Al
    参考文献:Chemistry - A European Journal 日期:2001 卷标:7(16) 页码:3533-3544]

    61413-54-5 = 85416-73-5 [标题:Reaction Conditions
    标题:Crystal Structure,Absolute Configuration,And Phosphodiesterase Inhibitory Activity Of (+)-1-(4-Bromobenzyl)-4-[(3-Cyclopentyloxy)-4-Methoxyphenyl]-2-Pyrrolidinone
    作者:Baures,Paul W.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:1993 卷标:36(22) 页码:3274-7]

    1001860-35-0 = 85416-73-5
    反应条件:1.1 Reagents: Diisopropylethylamine,Trichlorosilane Solvents: Acetonitrile,Dichloromethane; 10 Min,5 Bar,Rt
    标题:Enantioselective Flow Synthesis Of Rolipram Enabled By A Telescoped Asymmetric Conjugate Addition-Oxidative Aldehyde Esterification Sequence Using In Situ-Generated Persulfuric Acid As Oxidant
    作者:Nagy,Bence S.; Et Al
    参考文献:Organic Letters 日期:2022 卷标:24(4) 页码:1066-1071]

    = 85416-73-5
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; Ph 14,0 °C; 2 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 11.3 Solvents: Toluene; 12 H,110 °C
    标题:Unprecedented Hydrophobic Amplification In Noncovalent Organocatalysis "On Water": Hydrophobic Chiral Squaramide Catalyzed Michael Addition Of Malonates To Nitroalkenes
    作者:Bae,Han Yong; Et Al
    参考文献:Acs Catalysis 日期:2015 卷标:5(6) 页码:3613-3619]

    = 85416-73-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: O-Xylene; 18 H,10 Bar,130 °C
    标题:Multisite Organic-Inorganic Hybrid Catalysts For The Direct Sustainable Synthesis Of Gabaergic Drugs
    作者:Leyva-Perez,Antonio; Et Al
    参考文献:Angewandte Chemie 日期:2014 卷标:53(33) 页码:8687-8690]

    1001860-35-0 = 85416-73-5
    反应条件:1.1 Reagents: Nickel Dichloride,Sodium Borohydride Solvents: Ethanol; 0 °C; 1 H,0 °C1.2 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 0 °C; 0 °C -> Rt; 30 Min,Rt
    标题:Bifunctional Iminophosphorane-Catalyzed Enantioselective Nitroalkane Addition To Unactivated α,β-Unsaturated Esters
    作者:Rozsar,Daniel; Et Al
    参考文献:Chemrxiv 日期:2022 卷标:1 页码:1-8]

    108-59-8 + 67387-76-2 = 85416-73-5
    反应条件:1.1 Catalysts: N-[3,5-Bis(Trifluoromethyl)Phenyl]-N′-[(9R)-6′-[[[[3-(Triethoxysilyl)Propyl]Amin... (Silica-Supported) Solvents: O-Xylene; 24 H,70 °C1.2 Reagents: Hydrogen Catalysts: Palladium; 2 H,130 °C
    标题:Multisite Organic-Inorganic Hybrid Catalysts For The Direct Sustainable Synthesis Of Gabaergic Drugs
    作者:Leyva-Perez,Antonio; Et Al
    参考文献:Angewandte Chemie 日期:2014 卷标:53(33) 页码:8687-8690]

    108-59-8 + 67387-76-2 = 85416-73-5
    反应条件:1.1 Catalysts: Calcium Chloride Solvents: Toluene; 1 W,75 °C1.2 Reagents: Triethylamine Catalysts: Calcium Chloride,Pyridine,2,6-Bis[(4S,5S)-4,5-Dihydro-4,5-Diphenyl-2-Oxazolyl]-4-Ethenyl-,Polym... Solvents: Toluene; 4 H,0 °C1.3 Reagents: Ammonium Chloride1.4 Reagents: Hydrogen Catalysts: Palladium,Water Solvents: Ethanol; 100 °C1.5 Solvents: O-Xylene,Water; 120 °C
    标题:Multistep Continuous-Flow Synthesis Of (R)- And (S)-Rolipram Using Heterogeneous Catalysts
    作者:Tsubogo,Tetsu; Et Al
    参考文献:Nature (London 日期:2015 卷标:520(7547) 页码:329-332]

    2640210-84-8 = 85416-73-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 12 H,60 °C1.2 Reagents: 4-Methylmorpholine,Isobutyl Chloroformate Solvents: Tetrahydrofuran; 15 Min,-15 °C1.3 Reagents: Triethylamine,2-Mercaptopyridine N-Oxide Solvents: Tetrahydrofuran; 1 H,-15 °C1.4 Reagents: Tert-Butyl Mercaptan Solvents: Tetrahydrofuran; 1 H,Rt
    标题:Enantioselective Synthesis Of Pyroglutamic Acid Esters From Glycinate Via Carbonyl Catalysis
    作者:Ma,Jiguo; Et Al
    参考文献:Angewandte Chemie 日期:2021 卷标:60(19) 页码:10588-10592]

    133332-47-5 = 85416-73-5
    反应条件:1.1 Catalysts: (2S)-2-[diphenyl[(Trimethylsilyl)Oxy]Methyl]Pyrrolidine Solvents: 1,4-Dioxane; 4 °C; 18 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Rt1.3 Reagents: Potassium Peroxymonosulfate Sulfate (2Khso5.Khso4.K2So4) Solvents: Dimethylformamide; 12 H,Rt1.4 Reagents: Chlorotrimethylsilane; 12 H,Rt1.5 Reagents: Sodium Bicarbonate Solvents: Water; Rt1.6 Reagents: Hydrogen Catalysts: Triethylamine,Palladium Solvents: Ethyl Acetate; 12 H,1 Atm,Rt
    标题:Efficient Synthesis Of (-)-(R)- And (+)-(S)-Rolipram
    作者:Kaur,Ramandeep; Et Al
    参考文献:Tetrahedron Letters 日期:2017 卷标:58(46) 页码:4333-4335]

    2642616-75-7 + 2642616-74-6 = 85416-73-5
    反应条件:1.1 Reagents: 4-Methylmorpholine,Isobutyl Chloroformate Solvents: Tetrahydrofuran; 15 Min,-15 °C1.2 Reagents: Triethylamine,2-Mercaptopyridine N-Oxide Solvents: Tetrahydrofuran; 1 H,-15 °C1.3 Reagents: Tert-Butyl Mercaptan Solvents: Tetrahydrofuran; 1 H,Rt
    标题:Enantioselective Synthesis Of Pyroglutamic Acid Esters From Glycinate Via Carbonyl Catalysis
    作者:Ma,Jiguo; Et Al
    参考文献:Angewandte Chemie 日期:2021 卷标:60(19) 页码:10588-10592]

    104-54-1 + 1427298-74-5 = 85416-73-5
    反应条件:1.1 Catalysts: Quinine Solvents: Toluene; 3 D,-30 °C1.2 Reagents: Hydrochloric Acid Solvents: Water2.1 Reagents: Triethylamine,Diphenylphosphoryl Azide Solvents: Toluene; 30 Min,90 °C; 90 °C -> Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Overnight,Rt; Overnight,110 °C; 110 °C -> Rt
    标题:A Simple Enantioselective Route Toward (R)- And (S)-Rolipram Via Anhydride Desymmetrization
    作者:Ivsic,Trpimir; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2013 卷标:24(4) 页码:217-222]

    1001860-35-0 = 85416-73-5
    反应条件:1.1 Reagents: Nickel Dichloride Solvents: Ethanol; Rt -> 0 °C1.2 Reagents: Sodium Borohydride; 0 °C; 1 H,0 °C1.3 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 0 °C; 0 °C -> Rt; 30 Min,Rt
    标题:Bifunctional Iminophosphorane-Catalyzed Enantioselective Nitroalkane Addition To Unactivated α,β-Unsaturated Esters
    作者:Rozsar,Daniel; Et Al
    参考文献:Angewandte Chemie 日期:2023 卷标:62(21)]

    1001860-35-0 = 85416-73-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; Overnight,Rt
    标题:Water-Compatible Iminium Activation: Organocatalytic Michael Reactions Of Carbon-Centered Nucleophiles With Enals
    作者:Palomo,Claudio; Et Al
    参考文献:Angewandte Chemie 日期:2007 卷标:46(44) 页码:8431-8435]

    1259130-31-8 = 85416-73-5
    反应条件:1.1 Reagents: Chlorotrimethylsilane,Zinc Solvents: Ethanol; 0 °C; 20 Min,Rt
    标题:A Heterobimetallic Ni/la-Salan Complex For Catalytic Asymmetric Decarboxylative 1,4-Addition Of Malonic Acid Half-Thioester
    作者:Furutachi,Makoto; Et Al
    参考文献:Chemistry - An Asian Journal 日期:2010 卷标:5(11) 页码:2351-2354]

    = 85416-73-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Methanol,Water; 12 H,45 Psi,Rt2.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; Ph 14,0 °C; 2 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 12.3 Solvents: Toluene; 12 H,110 °C
    标题:Unprecedented Hydrophobic Amplification In Noncovalent Organocatalysis "On Water": Hydrophobic Chiral Squaramide Catalyzed Michael Addition Of Malonates To Nitroalkenes
    作者:Bae,Han Yong; Et Al
    参考文献:Acs Catalysis 日期:2015 卷标:5(6) 页码:3613-3619]

    959799-63-4 = 85416-73-5
    反应条件:1.1 Solvents: Tetrahydrofuran; Rt1.2 Reagents: Hydrazine; 24 H,Rt1.3 Reagents: Triethylamine Solvents: Toluene; Rt -> 110 °C; 20 H,110 °C; 110 °C -> Rt
    标题:Rhodium-Catalyzed Asymmetric Addition Of Arylboronic Acids To γ-Phthalimido-Substituted-α,β-Unsaturated Carboxylic Acid Esters: An Approach To γ-Amino Acids
    作者:Han,Fuzhong; Et Al
    参考文献:Tetrahedron Letters 日期:2011 卷标:52(7) 页码:830-833]

    1427298-78-9 = 85416-73-5
    反应条件:1.1 Reagents: Triethylamine,Diphenylphosphoryl Azide Solvents: Toluene; 30 Min,90 °C; 90 °C -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Overnight,Rt; Overnight,110 °C; 110 °C -> Rt
    标题:A Simple Enantioselective Route Toward (R)- And (S)-Rolipram Via Anhydride Desymmetrization
    作者:Ivsic,Trpimir; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2013 卷标:24(4) 页码:217-222]

    1556-18-9 + 132683-31-9 = 85416-73-5
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Dimethylformamide; 40 H,60 °C
    标题:Elucidation Of A Structural Basis For The Inhibitor-Driven,P62 (Sqstm1)-Dependent Intracellular Redistribution Of Camp Phosphodiesterase-4A4 (Pde4A4)
    作者:Day,Jonathan P.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2011 卷标:54(9) 页码:3331-3347]

    = 85416-73-5
    反应条件:1.1 Solvents: Toluene; 12 H,110 °C
    标题:Unprecedented Hydrophobic Amplification In Noncovalent Organocatalysis "On Water": Hydrophobic Chiral Squaramide Catalyzed Michael Addition Of Malonates To Nitroalkenes
    作者:Bae,Han Yong; Et Al
    参考文献:Acs Catalysis 日期:2015 卷标:5(6) 页码:3613-3619]

    100-51-6 + 1427298-74-5 = 85416-73-5
    反应条件:1.1 Catalysts: Xanthene-9-Carboxylic Acid,Quinine Solvents: Toluene1.2 3 D,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water2.1 Reagents: Triethylamine,Diphenylphosphoryl Azide Solvents: Toluene; 30 Min,90 °C; 90 °C -> Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Overnight,Rt; Overnight,110 °C; 110 °C -> Rt
    标题:A Simple Enantioselective Route Toward (R)- And (S)-Rolipram Via Anhydride Desymmetrization
    作者:Ivsic,Trpimir; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2013 卷标:24(4) 页码:217-222
📜异香兰素置于sodium Tetrahydroborate,Nickel(II) Chloride Hexahydrate,乙醇,Potassium Carbonate,C80H88F12N3Ps,Lithium Hexamethyldisilazane体系中,用 四氢呋喃,环己烷,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 39.33H,反应生成 S-(+)-咯利普兰
参考文献:双功能亚氨基正膦催化对映选择性硝基烷加成至未活化的 α,β-不饱和酯**
标题:双功能亚氨基正膦催化对映选择性硝基烷加成至未活化的 α,β-不饱和酯**
摘要:描述了硝基烷烃与未活化的 α,β-不饱和酯的第一次分子间对映选择性加成,由双功能亚氨基正膦 (Bimp) 超强碱催化.这种基本的合成相关转化在多种原料底物上以高对映体过量和产率进行,只需一步即可提供药学相关的构建模块.
DOI:10.1002/anie.202303391

海关参考信息

专利信息


专利号:BR-122012005794-B1
优先权日:2002-09-11
标题 :racemic synthesis process of two new baclofen analogs

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主要参考文献

参考标题:Enantioselective Synthesis Of Pyroglutamic Acid Esters From Glycinate Via Carbonyl Catalysis
作者:Jiguo Ma,Qinghai Zhou,Guanshui Song,Yongchang Song,Guoqing Zhao,Kuiling Ding,Baoguo Zhao |发布日期:2021.5.3
摘要:Direct α‐functionalization Of Nh2‐free Glycinates With Relatively Weak Electrophiles Such As α,β‐unsaturated Esters Still Remains A Big Challenge In Organic Synthesis. With Chiral Pyridoxal 5 D As A Carbonyl Catalyst, Direct Asymmetric Conjugated Addition At The α‐c Of Glycinate 1 A With α,β‐unsaturated Esters 2 Has Been Successfully Realized, To Produce Various Chiral Pyroglutamic Acid Esters 4 In 14-96 %

合成参考文献


摘要:Aguilar, E.; López, L. A., Science of Synthesis Knowledge Updates, (2014) 2, 74.
摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
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