(1S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0^1,6]undecan-2-one | 418757-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0^1,6]undecan-2-one
• 英文别名: (2As,4aS,5R,8aS)-5-hydroxy-2,2,4a-trimethyl-2a,3,4,5,6,7-hexahydro-1H-cyclobuta[i]inden-8-one
• CAS: 418757-04-7
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: UHRWOVVMQAASAO-GZZJDILISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0^1,6]undecan-2-one 在 氢溴酸 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以95%的产率得到(1S,3S,5R,6S,9S)-3-bromo-5-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0^1,6]undecan-2-one
  参考文献：
  名称：

  摘要：

  Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded alpha,beta-unsaturated alpha-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated. which provide evidence that oxidation proceeds according to the following scheme: ketone-->alpha-bromoketone-->alpha,alpha-dibromoketone-->alpha,beta-unsaturated alpha-bromoketone.

  DOI：

  10.1023/a:1012737123973
• 作为产物：
  描述：

  caryophyllene oxide 在 potassium permanganate 作用下， 生成 (1S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0^1,6]undecan-2-one
  参考文献：
  名称：

  摘要：

  Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded alpha,beta-unsaturated alpha-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated. which provide evidence that oxidation proceeds according to the following scheme: ketone-->alpha-bromoketone-->alpha,alpha-dibromoketone-->alpha,beta-unsaturated alpha-bromoketone.

  DOI：

  10.1023/a:1012737123973

文献信息

• ——
  作者：M. S. Yusubov、L. A. Drygunova、A. V. Tkachev

  DOI：10.1023/a:1012737123973

  日期：——

  Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded alpha,beta-unsaturated alpha-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated. which provide evidence that oxidation proceeds according to the following scheme: ketone-->alpha-bromoketone-->alpha,alpha-dibromoketone-->alpha,beta-unsaturated alpha-bromoketone.