[(4S)-4-cyclohexyl-4-hydroxybut-2-ynyl] methyl carbonate | 790300-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: [(4S)-4-cyclohexyl-4-hydroxybut-2-ynyl] methyl carbonate
• CAS: 790300-23-1
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: MWBHVCWGJIVCEL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4S)-4-cyclohexyl-4-hydroxybut-2-ynyl] methyl carbonate 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以93%的产率得到[(Z,4S)-4-cyclohexyl-4-hydroxybut-2-enyl] methyl carbonate
  参考文献：
  名称：

  An Efficient, Stereoselective Approach to syn-1,2-Diols Protected as Cyclic Carbonates

  摘要：

  Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.

  DOI：

  10.1021/jo048985g
• 作为产物：
  描述：

  甲基羧酸-2-丙炔基酯 、 环己烷基甲醛 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.5h， 以87%的产率得到[(4S)-4-cyclohexyl-4-hydroxybut-2-ynyl] methyl carbonate
  参考文献：
  名称：

  An Efficient, Stereoselective Approach to syn-1,2-Diols Protected as Cyclic Carbonates

  摘要：

  Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.

  DOI：

  10.1021/jo048985g

文献信息

• An Efficient, Stereoselective Approach to <i>s</i><i>yn</i>-1,2-Diols Protected as Cyclic Carbonates
  作者：Yohan Georges、Yves Allenbach、Xavier Ariza、Jean-Marc Campagne、Jordi Garcia

  DOI：10.1021/jo048985g

  日期：2004.10.1

  Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.