methyl 4-(cyclopent-2-enyl)benzoate | 1190899-36-5

• 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: methyl 4-(cyclopent-2-enyl)benzoate
• 英文别名: Methyl 4-cyclopent-2-en-1-ylbenzoate
• CAS: 1190899-36-5
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: PRVBWLVXLYIUSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (E)-methyl 4-(2-cyclopropylvinyl)benzoate 在 bis(1,5-cyclooctadiene)nickel (0) 、 二茂铁 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 氘代苯 为溶剂， 生成 methyl 4-(cyclopent-2-enyl)benzoate
  参考文献：
  名称：

  Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement

  摘要：

  A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclo-propane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

  DOI：

  10.1021/jo901525u

文献信息

• Mild Two-Step Process for the Transition-Metal-Free Synthesis of Carbon−Carbon Bonds from Allylic Alcohols/Ethers and Grignard Reagents
  作者：Xinping Han、Yanhua Zhang、Jimmy Wu

  DOI：10.1021/ja100747n

  日期：2010.3.31

  A mild two-step process for the regioselective, transition-metal-free preparation of carbon-carbon bonds from allylic alcohols/ethers and Grignard reagents is described. This process obviates the need for the harsh deprotection conditions usually required for removal of methyl ethers. The synthesis is accomplished by photochemically promoted allylic substitution reactions of allylic alcohols and ethers

  描述了从烯丙醇/醚和格氏试剂中区域选择性、无过渡金属制备碳-碳键的温和两步法。该过程不需要去除甲醚通常所需的苛刻的脱保护条件。该合成是通过烯丙醇和醚与二乙基硫代磷酸的光化学促进的烯丙基取代反应，然后在过渡金属下与各种格氏试剂形成 sp(3)-sp(3) 或 sp(2)-sp(3) 键来完成的。免费条件。根据亲核试剂的性质，可以控制碳-碳键形成事件的区域选择性以提供四级或三级碳中心。