alpha-(2-溴-2-丙烯-1-基)-苯乙腈 | 137040-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: alpha-(2-溴-2-丙烯-1-基)-苯乙腈
• 英文名称: 4-Brom-2-phenyl-4-pentennitril
• 英文别名: 4-Bromo-2-phenylpent-4-enenitrile
• CAS: 137040-93-8
• 化学式: C₁₁H₁₀BrN
• 分子量: 236.111
• InChiKey: PCUOXYSNHJPTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  alpha-(2-溴-2-丙烯-1-基)-苯乙腈 在 正丁基锂 、 (4R,5R)-2-chloro-3,4-dimethyl-2-[(2-methylpropan-2-yl)oxy]-5-phenyl-1,3,2-oxazasilolidine 、 二异丙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 hexanes 、 2,3,4-三氟甲苯 为溶剂， 反应 39.67h， 生成 N'-[(3S,4R)-6-benzyl-4-cyano-1,4-diphenylhept-6-en-3-yl]benzohydrazide
  参考文献：
  名称：

  A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence

  摘要：

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.

  DOI：

  10.1021/ol201566u
• 作为产物：
  描述：

  苯乙腈 、 2,3-二溴-1-丙烯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 15.17h， 以46%的产率得到alpha-(2-溴-2-丙烯-1-基)-苯乙腈
  参考文献：
  名称：

  A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence

  摘要：

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.

  DOI：

  10.1021/ol201566u

文献信息

• Kauffmann, Thomas; Stach, Dirk, Chemische Berichte, 1992, vol. 125, # 4, p. 913 - 922
  作者：Kauffmann, Thomas、Stach, Dirk

  DOI：——

  日期：——
• A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence
  作者：Jenny M. Baxter Vu、James L. Leighton

  DOI：10.1021/ol201566u

  日期：2011.8.5

  A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that In turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.