(E)-methyl 3-(2-(2,2-dibromovinyl)-4-chlorophenyl)acrylate | 1229445-75-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 3-(2-(2,2-dibromovinyl)-4-chlorophenyl)acrylate
• 英文别名: methyl (E)-3-[4-chloro-2-(2,2-dibromoethenyl)phenyl]prop-2-enoate
• CAS: 1229445-75-3
• 化学式: C₁₂H₉Br₂ClO₂
• 分子量: 380.463
• InChiKey: HUCATZLBOUVIRC-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(2-(2,2-dibromovinyl)-4-chlorophenyl)acrylate 、 苯硼酸 在 caesium carbonate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-呋喃基)膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以71%的产率得到(E)-methyl 2-(5-chloro-2-phenyl-1H-inden-1-ylidene)acetate
  参考文献：
  名称：

  A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity

  摘要：

  The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction. The reaction is highly modular and proceeds under mild conditions. The choice of ligand was found to be crucial to control the selectivity of the reaction. Isolation of intermediates under different conditions provides insight into the mechanism.

  DOI：

  10.1021/ol100844v
• 作为产物：
  描述：

  四溴化碳 、 (E)-methyl 3-(4-chloro-2-formylphenyl)acrylate 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(E)-methyl 3-(2-(2,2-dibromovinyl)-4-chlorophenyl)acrylate
  参考文献：
  名称：

  A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity

  摘要：

  The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction. The reaction is highly modular and proceeds under mild conditions. The choice of ligand was found to be crucial to control the selectivity of the reaction. Isolation of intermediates under different conditions provides insight into the mechanism.

  DOI：

  10.1021/ol100844v

文献信息

• A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into <i>gem</i>-Dibromoolefin Reactivity
  作者：Christopher S. Bryan、Mark Lautens

  DOI：10.1021/ol100844v

  日期：2010.6.18

  The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction. The reaction is highly modular and proceeds under mild conditions. The choice of ligand was found to be crucial to control the selectivity of the reaction. Isolation of intermediates under different conditions provides insight into the mechanism.