6-Cyclohexylhex-5-ynoic acid | 211820-35-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-Cyclohexylhex-5-ynoic acid
• CAS: 211820-35-8
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: JFMMAXQNEMWROS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  6-Cyclohexylhex-5-ynoic acid 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(4-Cyclohexylbut-3-ynyl)pent-4-ene-1,3-diol
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Dienynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3. THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of dienynes. The catalyst's ability to insert the alkyne in preference to the alkenes in a regioselective manner, combined with the high diastereoselectivity of the intramolecular insertion process, leads to bicyclo[3.3.0]octane products in high yield. The stereochemistry of the exocyclic olefin, the ring fusion, and the ring substituents are all controlled in the reaction. The cyclization of dienynes thus affords silylated carbobicyclics with high diastereoselectivities in excellent yields.

  DOI：

  10.1021/jo980521t
• 作为产物：
  描述：

  6-Cyclohexyl-hex-5-yn-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到6-Cyclohexylhex-5-ynoic acid
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Dienynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3. THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of dienynes. The catalyst's ability to insert the alkyne in preference to the alkenes in a regioselective manner, combined with the high diastereoselectivity of the intramolecular insertion process, leads to bicyclo[3.3.0]octane products in high yield. The stereochemistry of the exocyclic olefin, the ring fusion, and the ring substituents are all controlled in the reaction. The cyclization of dienynes thus affords silylated carbobicyclics with high diastereoselectivities in excellent yields.

  DOI：

  10.1021/jo980521t

文献信息

• Sequential Cyclization/Silylation of Dienynes Catalyzed by an Organoyttrium Complex
  作者：Gary A. Molander、William H. Retsch

  DOI：10.1021/jo980521t

  日期：1998.8.1

  The organoyttrium complex Cp*2YCH3. THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of dienynes. The catalyst's ability to insert the alkyne in preference to the alkenes in a regioselective manner, combined with the high diastereoselectivity of the intramolecular insertion process, leads to bicyclo[3.3.0]octane products in high yield. The stereochemistry of the exocyclic olefin, the ring fusion, and the ring substituents are all controlled in the reaction. The cyclization of dienynes thus affords silylated carbobicyclics with high diastereoselectivities in excellent yields.