(1S,2R,6S,7R,9S)-9-hydroxy-9-methyl-11-(propan-2-yl)tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-one | 1144084-83-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,6S,7R,9S)-9-hydroxy-9-methyl-11-(propan-2-yl)tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-one
• 英文别名: (1S,2R,6S,7R,9S)-9-hydroxy-9-methyl-11-propan-2-yltricyclo[5.2.2.02,6]undeca-4,10-dien-8-one
• CAS: 1144084-83-2
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: BNZQXHQJYPBJGY-SHGFOSJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2R,3S,7S,8R,10S)-3,10-dihydroxydielmentha-5,11-diene-4,9-dione 、 dicyclopentadiene 以 均三甲苯 为溶剂， 反应 0.25h， 以98%的产率得到(1S,2R,6S,7R,9S)-9-hydroxy-9-methyl-11-(propan-2-yl)tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-one
  参考文献：
  名称：

  Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions ofo-Quinol Dimers

  摘要：

  We have accomplished a parallel screen of cycloaddition partners for o-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of o-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of o-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.

  DOI：

  10.1021/jo201658y

文献信息

• Enantioselective Synthesis of (+)‐Chamaecypanone C: A Novel Microtubule Inhibitor
  作者：Suwei Dong、Ernest Hamel、Ruoli Bai、David G. Covell、John A. Beutler、John A. Porco

  DOI：10.1002/anie.200805486

  日期：2009.2.9

  A bicycle built for tubulin: The total synthesis of (+)‐chamaecypanone C has been achieved by using a tandem retro‐Diels–Alder/Diels–Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)‐chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.

  为微管蛋白制造的自行车：通过使用串联逆 Diels-Alder/Diels-Alder 级联反应实现了 (+)-chamaecypanone C 的全合成（参见方案）。最初的生物学研究表明，(+)-chamaecypanone C 是微管蛋白组装的抑制剂，并在秋水仙碱位点结合。