(-)-(5R)-1-ethynyl-5-isopropenyl-2-methyl-2-cyclohexenol | 518037-97-3

• 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: (-)-(5R)-1-ethynyl-5-isopropenyl-2-methyl-2-cyclohexenol
• 英文别名: (1S,5S)-1-ethynyl-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
• CAS: 518037-97-3
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: CYYDSDIDECIOCI-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(5R)-1-ethynyl-5-isopropenyl-2-methyl-2-cyclohexenol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 (-)-(5R)-3-[2-dichloro(vinyl)silylethynyl]-5-isopropenyl-3-methoxy-2-methylcyclohexene
  参考文献：
  名称：

  摘要：

  Reaction of butyllithium with acetylene and 1-hexyne gave the corresponding lithium acetylides which reacted with (-)-(R)- and (+)-(S)-carvone in a stereospecific fashion to give lithium (1-ethynyl- or 1-hexynyl)-5-isopropenyl-2-methyl-2-cyclohexenolates. Hydrolysis of the latter gave individual optically active tertiary terpene alcohols having both acetylenic and p-menthene fragment. Their treatment with methyl iodide in the presence of hexamethylphosphoric triamide afforded the corresponding methyl ethers. The reaction of 3-ethynyl-5-isopropenyl-3-methoxy-2-methylcyclohexene with butyllithium and trichloro(vinyl)silane yielded optically active dichlorosilyl-containing acetylenic compounds.

  DOI：

  10.1023/a:1022587918015
• 作为产物：
  描述：

  lithium (-)-(5R)-1-ethynyl-5-isopropenyl-2-methyl-2-cyclohexenolate 在 水 作用下， 以87%的产率得到(-)-(5R)-1-ethynyl-5-isopropenyl-2-methyl-2-cyclohexenol
  参考文献：
  名称：

  摘要：

  Reaction of butyllithium with acetylene and 1-hexyne gave the corresponding lithium acetylides which reacted with (-)-(R)- and (+)-(S)-carvone in a stereospecific fashion to give lithium (1-ethynyl- or 1-hexynyl)-5-isopropenyl-2-methyl-2-cyclohexenolates. Hydrolysis of the latter gave individual optically active tertiary terpene alcohols having both acetylenic and p-menthene fragment. Their treatment with methyl iodide in the presence of hexamethylphosphoric triamide afforded the corresponding methyl ethers. The reaction of 3-ethynyl-5-isopropenyl-3-methoxy-2-methylcyclohexene with butyllithium and trichloro(vinyl)silane yielded optically active dichlorosilyl-containing acetylenic compounds.

  DOI：

  10.1023/a:1022587918015