(+)-(5S)-3-ethynyl-5-isopropenyl-3-methoxy-2-methylcyclohexene | 518037-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(5S)-3-ethynyl-5-isopropenyl-3-methoxy-2-methylcyclohexene
• CAS: 518037-93-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: DYCJLJDEFJEWOS-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  乙烯基三氯硅烷 、 (+)-(5S)-3-ethynyl-5-isopropenyl-3-methoxy-2-methylcyclohexene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以51%的产率得到(+)-(5S)-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 (+)-(5S)-1-ethynyl-5-isopropenyl-2-methyl-2-cyclohexenolate 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 (+)-(5S)-3-ethynyl-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