trans-methyl 3-((Z)-2-chloro-5-phenylpent-1-enyl)-2,2-dimethyl-1-cyclopropanecarboxylate

• 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: trans-methyl 3-((Z)-2-chloro-5-phenylpent-1-enyl)-2,2-dimethyl-1-cyclopropanecarboxylate
• 英文别名: methyl (1R,3S)-3-[(Z)-2-chloro-5-phenylpent-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• 化学式: C₁₈H₂₃ClO₂
• 分子量: 306.832
• InChiKey: ANARJSOZWYKMGQ-OPZRYQFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• 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：

  烯丙苯 、 3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸甲酯 在 tris(dibenzylideneacetone)dipalladium (0) 9-borabicyclo[3.3.1]nonane dimer 、 caesium carbonate 、 cesium fluoride 、 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 167.0h， 生成 trans-methyl 3-((E)-2-chloro-5-phenylpent-1-enyl)-2,2-dimethyl-1-cyclopropanecarboxylate 、 trans-methyl 3-((Z)-2-chloro-5-phenylpent-1-enyl)-2,2-dimethyl-1-cyclopropanecarboxylate 、 cis-methyl 3-((E)-2-chloro-5-phenylpent-1-enyl)-2,2-dimethyl-1-cyclopropanecarboxylate 、 cis-methyl 3-((Z)-2-chloro-5-phenylpent-1-enyl)-2,2-dimethyl-1-cyclopropanecarboxylate
  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.