1,1-dichloro-2-(2,4-dimethoxyphenyl)ethene | 934372-01-7

• 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: 1,1-dichloro-2-(2,4-dimethoxyphenyl)ethene
• 英文别名: 1-(2,2-Dichloroethenyl)-2,4-dimethoxybenzene
• CAS: 934372-01-7
• 化学式: C₁₀H₁₀Cl₂O₂
• 分子量: 233.094
• InChiKey: CJWMLIVFDBRVKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-dichloro-2-(2,4-dimethoxyphenyl)ethene 、 烯丙苯 在 tris(dibenzylideneacetone)dipalladium (0) 9-borabicyclo[3.3.1]nonane dimer 、 potassium fluoride 、 potassium phosphate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 为溶剂， 反应 45.0h， 以82%的产率得到(Z)-2-chloro-1-(2,4-dimethoxyphenyl)-5-phenylpent-1-ene
  参考文献：
  名称：

  Suzuki−Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBN

  摘要：

  We addressed an unexplored application of the Suzuki-Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P-Pd-P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.

  DOI：

  10.1021/jo061908w
• 作为产物：
  描述：

  2,2,2-trichloro-1-(2,4-dimethoxy-phenyl)-ethanol 在 吡啶 、 溶剂黄146 、 锌 作用下， 反应 5.0h， 生成 1,1-dichloro-2-(2,4-dimethoxyphenyl)ethene
  参考文献：
  名称：

  Suzuki−Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBN

  摘要：

  We addressed an unexplored application of the Suzuki-Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P-Pd-P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.

  DOI：

  10.1021/jo061908w

文献信息

• Suzuki−Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBN
  作者：Frédéric Liron、Céline Fosse、Alban Pernolet、Emmanuel Roulland

  DOI：10.1021/jo061908w

  日期：2007.3.1

  We addressed an unexplored application of the Suzuki-Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P-Pd-P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.