tert-butyl (S)-4-hydroxy-6-methylhept-2-ynyl carbonate | 790300-25-3

• 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: tert-butyl (S)-4-hydroxy-6-methylhept-2-ynyl carbonate
• 英文别名: tert-butyl [(4S)-4-hydroxy-6-methylhept-2-ynyl] carbonate
• CAS: 790300-25-3
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: AETCZWDBQSZVNN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  tert-butyl (S)-4-hydroxy-6-methylhept-2-ynyl carbonate 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以83%的产率得到tert-butyl [(Z,4S)-4-hydroxy-6-methylhept-2-enyl] 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：

  异戊醛 、 tert-butyl prop-2-yn-1-yl carbonate 在 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 tert-butyl (R)-4-hydroxy-6-methylhept-2-ynyl carbonate 、 tert-butyl (S)-4-hydroxy-6-methylhept-2-ynyl 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.