(Z)-2,5-dimethyldec-5-en-4-ol

• 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: (Z)-2,5-dimethyldec-5-en-4-ol
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: AEPSBNHXNGREHK-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-bromohexyne 、 Dimethylzinc 、 异戊醛 在 二溴硼烷 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以92%的产率得到(Z)-2,5-dimethyldec-5-en-4-ol
  参考文献：
  名称：

  A One-Pot Multicomponent Coupling Reaction for the Stereocontrolled Synthesis of (Z)-Trisubstituted Allylic Alcohols

  摘要：

  In this Communication, we outline a new one-pot, multicomponent coupling reaction that allows easy access to (Z)-trisubstituted allylic alcohols. Our strategy is based on E to Z isomerization of the 1-bromo-1-dialkylvinylborane upon reaction with dialkylzinc reagents, and subsequent transmetalation to give (Z)-trisubstituted vinylzinc species. In situ trapping of the reactive vinylzinc intermediates with aldehydes furnished a series of (Z)-trisubstituted allylic alcohols. This method represents a viable alternative to the Still-Gennari modification of the HWE olefination reaction, and it has the advantage that it allows coupling of larger fragments.

  DOI：

  10.1021/ja0396145

文献信息

• Kerrigan, Michael H.; Jeon, Sang-Jin; Chen, Young K., Journal of the American Chemical Society, 2009, vol. 131, p. 8434 - 8445
  作者：Kerrigan, Michael H.、Jeon, Sang-Jin、Chen, Young K.、Salvi, Luca、Carroll, Patrick J.、Walsh, Patrick J.

  DOI：——

  日期：——
• A One-Pot Multicomponent Coupling Reaction for the Stereocontrolled Synthesis of (<i>Z</i>)-Trisubstituted Allylic Alcohols
  作者：Young K. Chen、Patrick J. Walsh

  DOI：10.1021/ja0396145

  日期：2004.3.1

  In this Communication, we outline a new one-pot, multicomponent coupling reaction that allows easy access to (Z)-trisubstituted allylic alcohols. Our strategy is based on E to Z isomerization of the 1-bromo-1-dialkylvinylborane upon reaction with dialkylzinc reagents, and subsequent transmetalation to give (Z)-trisubstituted vinylzinc species. In situ trapping of the reactive vinylzinc intermediates with aldehydes furnished a series of (Z)-trisubstituted allylic alcohols. This method represents a viable alternative to the Still-Gennari modification of the HWE olefination reaction, and it has the advantage that it allows coupling of larger fragments.