[(E)-12-pentadecen-10-ynyl] benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(E)-12-pentadecen-10-ynyl] benzoate
• 英文别名: [(E)-pentadec-12-en-10-ynyl] benzoate
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: HRVGRCTZRCUVCI-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反-3-已烯 、 Benzoic acid tridec-12-en-10-ynyl ester 在 Grubbs catalyst third generation 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 [(Z)-12-pentadecen-10-ynyl] benzoate 、 [(E)-12-pentadecen-10-ynyl] benzoate
  参考文献：
  名称：

  Substituent Effects on the Z/E-Selectivity in Cross-Metathesis of Conjugated Enynes

  摘要：

  Cross-metathesis of a range of conjugated enynes with alkenes turns out to proceed with preferential formation of Z-isomers over E-isomers up to >25:1. Careful studies including substrate modification and control experiments revealed that the reaction proceeds under kinetic rather than thermodynamic control. Driving forces for this substrate-dependent Z-selectivity are attributed to the steric hindrance between substituents on the reacting enynes and NHC ligand of the ruthenium catalyst in the putative metallacyclobutane, as well as chelation effects of suitably positioned functional groups to Ru, which is strongly supported by ab initio calculations.

  DOI：

  10.1021/jo048883q

文献信息

• Substituent Effects on the <i>Z/E</i>-Selectivity in Cross-Metathesis of Conjugated Enynes
  作者：Byungman Kang、Ji Min Lee、Jaesik Kwak、Yoon Sup Lee、Sukbok Chang

  DOI：10.1021/jo048883q

  日期：2004.10.1

  Cross-metathesis of a range of conjugated enynes with alkenes turns out to proceed with preferential formation of Z-isomers over E-isomers up to >25:1. Careful studies including substrate modification and control experiments revealed that the reaction proceeds under kinetic rather than thermodynamic control. Driving forces for this substrate-dependent Z-selectivity are attributed to the steric hindrance between substituents on the reacting enynes and NHC ligand of the ruthenium catalyst in the putative metallacyclobutane, as well as chelation effects of suitably positioned functional groups to Ru, which is strongly supported by ab initio calculations.