(1R)-1,5,5-trimethyl-6-methylene-2-oxocyclohexylacetic acid | 302840-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1,5,5-trimethyl-6-methylene-2-oxocyclohexylacetic acid
• 英文别名: 2-[(1R)-1,3,3-trimethyl-2-methylidene-6-oxocyclohexyl]acetic acid
• CAS: 302840-44-4
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: PZEQSAKCYFISTL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R)-1,5,5-trimethyl-6-methylene-2-oxocyclohexylacetic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.17h， 生成 methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate
  参考文献：
  名称：

  An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol

  摘要：

  The first enantiospecific synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of three contiguous quaternary carbon atoms present in the thapsane framework. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01107-2
• 作为产物：
  描述：

  (+)-methyl (1R)-1,5,5-trimethyl-6-methylenecyclohex-3-en-2-one-1-acetate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 12.5h， 生成 (1R)-1,5,5-trimethyl-6-methylene-2-oxocyclohexylacetic acid
  参考文献：
  名称：

  An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol

  摘要：

  The first enantiospecific synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo- and regiospecific generation of three contiguous quaternary carbon atoms present in the thapsane framework. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01107-2

文献信息

• Srikrishna; Anebouselvy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 6, p. 776 - 788
  作者：Srikrishna、Anebouselvy

  DOI：——

  日期：——
• Srikrishna; Anebouselvy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 3, p. 449 - 459
  作者：Srikrishna、Anebouselvy

  DOI：——

  日期：——