(5R)-2-ethylidene-5-methylcyclohexanol | 1101168-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R)-2-ethylidene-5-methylcyclohexanol
• CAS: 1101168-99-3
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: FFDWZCOBGANIBG-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  一氧化碳 、 (5R)-2-ethylidene-5-methylcyclohexanol 在 2,4,6-三甲基吡啶 、 十二羰基三钌 作用下， 100.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以72.6%的产率得到(6R,7aS)-3,6-dimethyl-5,6,7,7a-tetrahydro-2(4H)-benzofuranone
  参考文献：
  名称：

  Practical Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols in 2,4,6-Collidine Leading to α,β-Unsaturated Lactones: Concise Stereoselective Synthesis of (+)-Isomintlactone

  摘要：

  We have found that ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine under atmospheric pressure of carbon monoxide smoothly proceeds to afford alpha,beta-unsaturated five- and six-membered lactones in moderate to good yields. Furthermore, we have completed a highly stereoselective synthesis of (+)-isomintlactone by the cyclocarbonylation of allenyl alcohol using 2,4,6-collidine.

  DOI：

  10.1021/jo8025127
• 作为产物：
  描述：

  [(6R)-8,8-diethoxy-6-methyloct-2-yn-1-yl](trimethyl)silane 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以74.5%的产率得到(5R)-2-ethylidene-5-methylcyclohexanol
  参考文献：
  名称：

  Practical Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols in 2,4,6-Collidine Leading to α,β-Unsaturated Lactones: Concise Stereoselective Synthesis of (+)-Isomintlactone

  摘要：

  We have found that ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine under atmospheric pressure of carbon monoxide smoothly proceeds to afford alpha,beta-unsaturated five- and six-membered lactones in moderate to good yields. Furthermore, we have completed a highly stereoselective synthesis of (+)-isomintlactone by the cyclocarbonylation of allenyl alcohol using 2,4,6-collidine.

  DOI：

  10.1021/jo8025127