CAS: 82508-31-4; (2E,4E)-5-((3R,4S,4As,9Ar)-4A-Acetoxy-7-(Methoxycarbonyl)-3-Methyl-1-Oxo-3,4,4A,5,6,9-Hexahydro-1H-4,9A-Ethanocyclohepta[c]Pyran-3-yl)-2-Methylpenta-2,4-Dienoic Acid

该化合物是一种天然化合物,被归类为三叶虫,主要产自普塞多拉里克斯-阿比里斯树的木材,通称为金发;该化合物因其结构复杂而引人注目,包括多个环和功能组,有助于其生物活动;Pseudolaric酸B具有各种药理特性,包括防炎,抗芬格尔和潜在的抗癌影响,使其成为医药化学和天然产品研究的热门;其行动机制往往涉及细胞路径的调节,尽管具体目标可能有所不同;该化合物通常在传统医学和现代治疗应用方面进行研究;在物理特性方面,普塞多拉里酸B通常以有机溶剂的溶性及水溶性有限为特征,这在许多三肢类动物中很常见.随着研究的继续,Pseudolaric酸B行动的潜在应用和机制可能会为新的治疗战略提供见解.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

C&L通报

上下游产品

CAS号1000669-90-8 (1R,7S,8S,9S)-7... | CAS号128836-43-1 3-iodo-2-methyl... | CAS号457622-27-4 methyl (3S,4R,4... | CAS号457622-33-2 methyl (3S,4R,4... | CAS号457622-30-9 methyl (3R,4R,4... | CAS号457622-31-0 methyl (3R,4R,4...

合成工艺路线路线简述

  • 128836-43-1 = 82508-31-4
    反应条件:1.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; 17 H,Rt; 5 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2007 卷标:129(47) 页码:14556-14557]

    = 82508-31-4 [标题:Reaction Conditions
    标题:Formal Synthesis Of Pseudolaric Acid B
    作者:Mori,Naoki
    参考文献:Synlett 日期:2020 卷标:31(9) 页码:907-910]

    1000669-90-8 = 82508-31-4
    反应条件:1.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; Rt; 15 Min,Rt2.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; Rt; 22 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(48) 页码:16424-16434]

    = 82508-31-4
    反应条件:1.1 Reagents: Dess-Martin Periodinane Solvents: Dichloromethane; 30 Min,Rt2.1 -
    标题:Formal Synthesis Of Pseudolaric Acid B
    作者:Mori,Naoki
    参考文献:Synlett 日期:2020 卷标:31(9) 页码:907-910]

    = 82508-31-4
    反应条件:1.1 Catalysts: Scandium Triflate Solvents: Acetic Anhydride; 0 °C; 2 H,0 °C2.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; Rt; 15 Min,Rt3.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; Rt; 22 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(48) 页码:16424-16434]

    = 82508-31-4
    反应条件:1.1 Reagents: Zinc Acetate Solvents: Methanol,Chloroform; 16 H,60 °C2.1 Reagents: Tris[(1-Benzyl-1H-1,2,3-Triazol-4-Yl)Methyl]Amine Catalysts: Sodium Ascorbate,Copper Sulfate Solvents: Methanol,Chloroform,Dimethyl Sulfoxide,Water; 4 H,30 °C3.1 Solvents: Dimethyl Sulfoxide,Water; 300 S,Ph 7.4,Rt
    标题:Direct 3-Acylation Of Indolizines By Carboxylic Acids For The Practical Synthesis Of Red Light-Releasable Caged Carboxylic Acids
    作者:Watanabe,Kenji; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(17) 页码:11822-11834]

    609-08-5 = 82508-31-4
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Diethyl Ether; 15 Min,Rt; 3 H,Reflux; Reflux -> 23 °C1.2 23 °C; 20 H,Reflux; Reflux -> 0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 0 °C2.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; Rt; 20 H,Reflux; Reflux -> 23 °C3.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; Rt; 22 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(48) 页码:16424-16434]

    = 82508-31-4
    反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 0 °C; 20 Min,23 °C2.1 Catalysts: Scandium Triflate Solvents: Acetic Anhydride; 0 °C; 2 H,0 °C3.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; Rt; 15 Min,Rt4.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; Rt; 22 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(48) 页码:16424-16434]

    = 82508-31-4
    反应条件:1.1 Solvents: Dimethyl Sulfoxide,Water; 300 S,Ph 7.4,Rt
    标题:Direct 3-Acylation Of Indolizines By Carboxylic Acids For The Practical Synthesis Of Red Light-Releasable Caged Carboxylic Acids
    作者:Watanabe,Kenji; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(17) 页码:11822-11834]

    128836-43-1 = 82508-31-4
    反应条件:1.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; Rt; 22 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(48) 页码:16424-16434]

    82508-32-5 = 82508-31-4 [标题:Reaction Conditions
    标题:Total Synthesis Of Pseudolaric Acid A
    作者:Geng,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2006 卷标:45(37) 页码:6197-6201]

    98891-41-9 = 82508-31-4
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol
    标题:Thermodynamic Theory Of Gases On Solid Interface Adsorption Isotherms
    作者:Li,Xueliang; Et Al
    参考文献:Huaxue Tongbao 日期:1995 卷标:(7) 页码:57-61]

    1000669-90-8 = 82508-31-4
    反应条件:1.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 15 Min,Rt2.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; 17 H,Rt; 5 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2007 卷标:129(47) 页码:14556-14557]

    = 82508-31-4
    反应条件:1.1 Reagents: Tris[(1-Benzyl-1H-1,2,3-Triazol-4-Yl)Methyl]Amine Catalysts: Sodium Ascorbate,Copper Sulfate Solvents: Methanol,Chloroform,Dimethyl Sulfoxide,Water; 4 H,30 °C2.1 Solvents: Dimethyl Sulfoxide,Water; 300 S,Ph 7.4,Rt
    标题:Direct 3-Acylation Of Indolizines By Carboxylic Acids For The Practical Synthesis Of Red Light-Releasable Caged Carboxylic Acids
    作者:Watanabe,Kenji; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(17) 页码:11822-11834]

    311807-55-3 = 82508-31-4
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; Rt; 20 H,Reflux; Reflux -> 23 °C2.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; Rt; 22 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2008 卷标:130(48) 页码:16424-16434]

    311807-55-3 = 82508-31-4
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 20 H,Reflux; Reflux -> 23 °C1.2 Reagents: Potassium Carbonate,Hydrochloric Acid Solvents: Dichloromethane,Water; Ph 1,23 °C2.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; 17 H,Rt; 5 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2007 卷标:129(47) 页码:14556-14557]

    82508-37-0 = 82508-31-4
    反应条件:1.1 Reagents: 4-(Dimethylamino)Pyridine; 8 H,Rt2.1 -
    标题:Total Synthesis Of Pseudolaric Acid A
    作者:Geng,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2006 卷标:45(37) 页码:6197-6201]

    = 82508-31-4
    反应条件:1.1 Catalysts: Scandium Triflate Solvents: Acetic Anhydride; 2 H,0 °C2.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 15 Min,Rt3.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; 17 H,Rt; 5 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2007 卷标:129(47) 页码:14556-14557]

    917-54-4 = 82508-31-4
    反应条件:1.1 Reagents: Cerium Trichloride Solvents: Diethyl Ether,Tetrahydrofuran; 30 Min,-78 °C1.2 Solvents: Tetrahydrofuran; 1 H,-78 °C1.3 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: Dess-Martin Periodinane Solvents: Dichloromethane; 30 Min,Rt3.1 -
    标题:Formal Synthesis Of Pseudolaric Acid B
    作者:Mori,Naoki
    参考文献:Synlett 日期:2020 卷标:31(9) 页码:907-910]

    609-08-5 = 82508-31-4
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Diethyl Ether; 3 H,Reflux; Reflux -> 23 °C1.2 20 H,Reflux; Reflux -> 0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 0 °C2.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 20 H,Reflux; Reflux -> 23 °C2.2 Reagents: Potassium Carbonate,Hydrochloric Acid Solvents: Dichloromethane,Water; Ph 1,23 °C3.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; 17 H,Rt; 5 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2007 卷标:129(47) 页码:14556-14557]

    = 82508-31-4
    反应条件:1.1 Reagents: Acetic Acid Solvents: Water; 0.5 H,60 °C; 60 °C -> Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water; Ph 71.3 Reagents: Dess-Martin Periodinane Solvents: Dichloromethane; 1 H,Rt1.4 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 7 H,Rt2.1 Reagents: 4-(Dimethylamino)Pyridine; 8 H,Rt3.1 -
    标题:Total Synthesis Of Pseudolaric Acid A
    作者:Geng,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2006 卷标:45(37) 页码:6197-6201]

    = 82508-31-4
    反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 0 °C; 20 Min,23 °C2.1 Catalysts: Scandium Triflate Solvents: Acetic Anhydride; 2 H,0 °C3.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 15 Min,Rt4.1 Reagents: Diisopropylethylamine Catalysts: Tris(Dibenzylideneacetone)Dipalladium Solvents: N-Methyl-2-Pyrrolidone; 17 H,Rt; 5 H,Rt
    标题:Total Synthesis Of (-)-Pseudolaric Acid B
    作者:Trost,Barry M.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2007 卷标:129(47) 页码:14556-14557]

    = 82508-31-4
    反应条件:1.1 Reagents: Dess-Martin Periodinane Solvents: Dichloromethane; 30 Min,Rt2.1 Reagents: Cerium Trichloride Solvents: Diethyl Ether,Tetrahydrofuran; 30 Min,-78 °C2.2 Solvents: Tetrahydrofuran; 1 H,-78 °C2.3 Reagents: Ammonium Chloride Solvents: Water3.1 Reagents: Dess-Martin Periodinane Solvents: Dichloromethane; 30 Min,Rt4.1 -
    标题:Formal Synthesis Of Pseudolaric Acid B
    作者:Mori,Naoki
    参考文献:Synlett 日期:2020 卷标:31(9) 页码:907-910]

    = 82508-31-4
    反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; 30 Min,0 °C1.2 Solvents: Tetrahydrofuran; 5 H,0 °C -> Rt1.3 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: Acetic Acid Solvents: Water; 0.5 H,60 °C; 60 °C -> Rt2.2 Reagents: Sodium Bicarbonate Solvents: Water; Ph 72.3 Reagents: Dess-Martin Periodinane Solvents: Dichloromethane; 1 H,Rt2.4 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 7 H,Rt3.1 Reagents: 4-(Dimethylamino)Pyridine; 8 H,Rt4.1 -
    标题:Total Synthesis Of Pseudolaric Acid A
    作者:Geng,Zhe; Et Al
    参考文献:Angewandte Chemie 日期:2006 卷标:45(37) 页码:6197-6201]

    516493-93-9 + 553-12-8 = 82508-31-4
    反应条件:1.1 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 20 H,30 °C2.1 Reagents: Zinc Acetate Solvents: Methanol,Chloroform; 16 H,60 °C3.1 Reagents: Tris[(1-Benzyl-1H-1,2,3-Triazol-4-Yl)Methyl]Amine Catalysts: Sodium Ascorbate,Copper Sulfate Solvents: Methanol,Chloroform,Dimethyl Sulfoxide,Water; 4 H,30 °C4.1 Solvents: Dimethyl Sulfoxide,Water; 300 S,Ph 7.4,Rt
    标题:Direct 3-Acylation Of Indolizines By Carboxylic Acids For The Practical Synthesis Of Red Light-Releasable Caged Carboxylic Acids
    作者:Watanabe,Kenji; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(17) 页码:11822-11834
📜(3S,3As)-3A-Hydroxy-3-((R)-1-Phenylselanylcarbonyloxyethyl)-1,2,3,3A,4,5-Hexahydroazulene-6-Carboxylic Acid Methyl Ester置于bis-Triphenylphosphine-Palladium(II) Chloride,正丁基锂,Otera'S Catalyst,Potassium Trimethylsilonate,四丁基氟化铵,三正丁基氢锡,碳酸氢钠,戴斯-马丁氧化剂,2,3-二氯-5,6-二氰基-1,4-苯醌,Scandium Tris(Trifluoromethanesulfonate),1,1'-偶氮(氰基环己烷)体系中,用 四氢呋喃,正己烷,二氯甲烷,甲苯,乙腈,苯 作为反应溶剂,化学反应 47.16H,反应生成 土槿皮乙酸
参考文献:(-)-Pseudolaric Acid B 的总合成
标题:(-)-Pseudolaric Acid B 的总合成
摘要:我们报告了我们对 Pseudolaric Acid B (1A) 全合成的工作,Pseudolaric Acid B (1A) 是一种从 Pseudolarix Kaempferi Gordon(松科)树皮中分离的二萜酸.化合物 1A 是一种抗真菌和抗生育剂.此外,它抑制微管蛋白聚合的能力使其成为癌症治疗的潜在线索.在本文中,我们描述了使用炔烃和乙烯基环丙烷的 Ru 或 Rh 催化 [5 + 2] 分子内环加成反应来构建分子的聚氢氮核心.我们第一个基于氰化物环氧化物开口的四元中心引入的不成功策略导致了发现一种新的 Tbaf 介导的 1,4-二烯到 1,3-二烯的异构化和环氧化物的乙烯基消除开口以形成二烯醇.我们的第二种策略,基于烷氧基羰基自由基在二烯系统上的环化,成功地形成了四元中心.详细的研究表明,这种未充分利用的内酯合成方法对底物结构和反应条件的依赖性.在合成的后期,证明了铈有机金属试
DOI:10.1021/ja806724X

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主要参考文献


1: Zhang J, Han RY, Ye HC, Zhou Y, Zhang ZK, Yuan EL, Li Y, Yan C, Liu X, Feng G, Guo YX. Effect of pseudolaric acid B on biochemical and physiologic characteristics in Colletotrichum gloeosporioides. Pestic Biochem Physiol. 2018 May;147:75-82. doi: 10.1016/j.pestbp.2017.09.006. Epub 2017 Sep 13. doi: 10.1016/j.canlet.2018.04.021. Epub 2018 Apr 24. doi: 10.1016/j.intimp.2018.03.041. Epub 2018 Apr 7. Chinese. doi: 10.3892/ol.2017.7426. Epub 2017 Nov 15.
6: Song Q, Jiang S, Zhang X, Pan C, Lu C, Peng J, Li Q. Radiosensitivity of human ovarian cancer cells is enhanced by pseudolaric acid B due to the inhibition of the Ras/Raf/ERK signaling pathway. Exp Ther Med. 2018 Jan;15(1):685-690. doi: 10.3892/etm.2017.5500. Epub 2017 Nov 13.
7: Li X, Zhao X, Song W, Tian Z, Yang L, Niu Q, Zhang Q, Xie M, Zhou B, Xu Y, Wu J, Zhang C. Pseudolaric Acid B Inhibits Proliferation, Invasion and Epithelial-to-Mesenchymal Transition in Human Pancreatic Cancer Cell. Yonsei Med J. 2018 Jan;59(1):20-27. doi: 10.3349/ymj.2018.59.1.20.

合成参考文献


摘要:US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Feb 7, 2013:
摘要:Jaradat MS et al; Planta Med. 68 (8): 667-71 (2002)
摘要:
摘要:
摘要:Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)
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