(Z)-2-chloro-1-(4-methoxyphenyl)-5-phenylpent-1-ene | 934372-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-2-chloro-1-(4-methoxyphenyl)-5-phenylpent-1-ene
• 英文别名: 1-[(Z)-2-chloro-5-phenylpent-1-enyl]-4-methoxybenzene
• CAS: 934372-04-0
• 化学式: C₁₈H₁₉ClO
• 分子量: 286.801
• InChiKey: BBNROFFDAHJPFR-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-chloro-1-(4-methoxyphenyl)-5-phenylpent-1-ene 、 苯硼酸 在 tris(dibenzylideneacetone)dipalladium (0) [1,1'-biphenyl]-2-yldicyclohexylphosphine oxide 、 potassium fluoride 、 potassium phosphate 作用下， 以 四氢呋喃 为溶剂， 反应 97.0h， 以66%的产率得到(Z)-2,5-diphenyl-1-(4-methoxyphenyl)pent-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：

  2,2,2-三氯-1-(4-甲氧基苯基)乙醇 在 9-borabicyclo[3.3.1]nonane dimer 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 (Z)-2-chloro-1-(4-methoxyphenyl)-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

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.