2-bromo-1-cyclohexylhexa-1,3,5-triene | 914478-71-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromo-1-cyclohexylhexa-1,3,5-triene
• 英文别名: [(1Z,3E)-2-bromohexa-1,3,5-trienyl]cyclohexane
• CAS: 914478-71-0
• 化学式: C₁₂H₁₇Br
• 分子量: 241.171
• InChiKey: GKWXEFCHAQELDG-VIXQYLIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-cyclohexylhexa-1,3,5-triene 、 乙酰氨基丙二酸二乙酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 diethyl 2-(6-cyclohexyl-1,4,5-hexatrien-3-yl)-2-(acetylamino)propane-1,3-dioate 、 diethyl 2-(6-cyclohexyl-2,4,5-hexatrienyl)-2-(acetylamino)propane-1,3-dioate
  参考文献：
  名称：

  Palladium-Catalyzed Preparation of Vinylallenes from 2-Bromo-1,3,5-trienes via an Alkylidene-π-allylpalladium-Mediated Formal S_N2‘ ‘ Pathway

  摘要：

  [GRAPHICS]A novel Pd-catalyzed reaction to prepare conjugated vinylallenes from 2-bromo-1,3,5-triene and a soft nucleophile via a formal S(N)2" pathway was developed. The reaction proceeds via alkylidene-d-allylpalladium and allenyl-d-allylpalladium intermediates, and a dynamic process involving the two palladium intermediates played important roles in determining the selectivity of the Pd-catalyzed reaction. The reaction was extended to an asymmetric counterpart, and an axially chiral vinylallene was obtained with up to 81% ee.

  DOI：

  10.1021/ol062309e
• 作为产物：
  描述：

  、 1,1-dibromo-2-cyclohexylethene 在 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-bromo-1-cyclohexylhexa-1,3,5-triene
  参考文献：
  名称：

  Palladium-Catalyzed Preparation of Vinylallenes from 2-Bromo-1,3,5-trienes via an Alkylidene-π-allylpalladium-Mediated Formal S_N2‘ ‘ Pathway

  摘要：

  [GRAPHICS]A novel Pd-catalyzed reaction to prepare conjugated vinylallenes from 2-bromo-1,3,5-triene and a soft nucleophile via a formal S(N)2" pathway was developed. The reaction proceeds via alkylidene-d-allylpalladium and allenyl-d-allylpalladium intermediates, and a dynamic process involving the two palladium intermediates played important roles in determining the selectivity of the Pd-catalyzed reaction. The reaction was extended to an asymmetric counterpart, and an axially chiral vinylallene was obtained with up to 81% ee.

  DOI：

  10.1021/ol062309e

文献信息

• Palladium-Catalyzed Preparation of Vinylallenes from 2-Bromo-1,3,5-trienes via an Alkylidene-π-allylpalladium-Mediated Formal S_N2‘ ‘ Pathway
  作者：Masamichi Ogasawara、Liyan Fan、Yonghui Ge、Tamotsu Takahashi

  DOI：10.1021/ol062309e

  日期：2006.11.9

  [GRAPHICS]A novel Pd-catalyzed reaction to prepare conjugated vinylallenes from 2-bromo-1,3,5-triene and a soft nucleophile via a formal S(N)2" pathway was developed. The reaction proceeds via alkylidene-d-allylpalladium and allenyl-d-allylpalladium intermediates, and a dynamic process involving the two palladium intermediates played important roles in determining the selectivity of the Pd-catalyzed reaction. The reaction was extended to an asymmetric counterpart, and an axially chiral vinylallene was obtained with up to 81% ee.