1-Isopropenyl-ethinylcyclohexanol | 13152-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Isopropenyl-ethinylcyclohexanol
• 英文别名: 1-(3-methyl-but-3-en-1-ynyl)-cyclohexanol；1-Hydroxy-1-(3-methyl-buten-(3)-in-(1)-yl)-cyclohexan；1-(3-Methyl-but-3-en-1-inyl)-cyclohexanol；1-(3-Methylbut-3-en-1-ynyl)cyclohexan-1-ol
• CAS: 13152-68-6
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: ODGIGBOAINFORA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  1-Isopropenyl-ethinylcyclohexanol 在 lithium aluminium tetrahydride 、 水 作用下， 生成 1-((E)-3-Methyl-buta-1,3-dienyl)-cyclohexanol
  参考文献：
  名称：

  Khrimyan, A. P.; Garibyan, O. A.; Panosyan, G. A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 12, p. 1961 - 1973

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 、 2-甲基-1-丁烯-3-炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-Isopropenyl-ethinylcyclohexanol
  参考文献：
  名称：

  Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂

  摘要：

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.

  DOI：

  10.1021/jo3009403

文献信息

• Lemiere, Gilles; Gandon, Vincent; Cariou, Kevin, Journal of the American Chemical Society, 2009, vol. 131, p. 2993 - 3006
  作者：Lemiere, Gilles、Gandon, Vincent、Cariou, Kevin、Hours, Alexandra、Fukuyama, Takahide、et al.

  DOI：——

  日期：——
• Nasarow, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1938, p. 704
  作者：Nasarow

  DOI：——

  日期：——
• The intramolecular enyne diels-alder reaction. Stereoselective construction of tricyclic dioxadienones and mechanistic outline
  作者：H.M.R. Hoffmann、D. Krumwiede、B. Mucha、H.H. Oehlerking、G.W. Prahst

  DOI：10.1016/s0040-4020(01)91218-9

  日期：1993.1

  4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H pyran 3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides. A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.
• Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂
  作者：Wei Chen、Jia-Hui Tay、Xiao-Qi Yu、Lin Pu

  DOI：10.1021/jo3009403

  日期：2012.7.20

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.
• Khrimyan, A. P.; Garibyan, O. A.; Panosyan, G. A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 12, p. 1961 - 1973
  作者：Khrimyan, A. P.、Garibyan, O. A.、Panosyan, G. A.、Mailyan, N. Sh.、Kinoyan, F. S.、et al.

  DOI：——

  日期：——