4-Bromo-benzoic acid (3aS,4S,5S,6R,8S,8aS)-5-hydroxy-3a,4,5,8a-tetramethyl-decahydro-4,8-methano-azulen-6-yl ester | 140848-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Bromo-benzoic acid (3aS,4S,5S,6R,8S,8aS)-5-hydroxy-3a,4,5,8a-tetramethyl-decahydro-4,8-methano-azulen-6-yl ester
• CAS: 140848-14-2
• 化学式: C₂₂H₂₉BrO₃
• 分子量: 421.374
• InChiKey: OKINENYAFIVBAA-JIUNHRLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,2,6,10-tetramethyltricyclo<5.3.1.02,6>undec-9-ene 在 吡啶 、 四氧化锇 作用下， 以 乙醚 为溶剂， 反应 0.03h， 生成 4-Bromo-benzoic acid (3aS,4S,5S,6R,8S,8aS)-5-hydroxy-3a,4,5,8a-tetramethyl-decahydro-4,8-methano-azulen-6-yl ester
  参考文献：
  名称：

  Cyclization and Rearrangements of Farnesol and Nerolidol Stereoisomers in Superacids

  摘要：

  Acid-catalyzed cyclization of 2,3-trans- and 2,3-cis-farensol proceeds regioselectively and stereospecifically, yielding drimenol and epi-drimenol, respectively. The trans and cis isomers of nerolidol undergo carbo- and heterocyclization reactions. The trans isomer gives tricyclic caged hydrocarbons with new skeletal types, while the rearrangements of the cis isomer produce derivatives of 2-oxabicyclo-[4.4.0]decane. The ICAR computer program was used to derive reasonable mechanisms for the acid-catalyzed transformations of nerolidol, and the probability of the mechanisms was evaluated by the molecular mechanics method.

  DOI：

  10.1021/jo00085a044

文献信息

• Polovinka, M. P.; Unzur, N. D.; Perutskii, V. B., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1871 - 1885
  作者：Polovinka, M. P.、Unzur, N. D.、Perutskii, V. B.、Korchagina, D. V.、Gatilov, Yu. V.、et al.

  DOI：——

  日期：——