2-bromo-hex-2-enoyl chloride | 727425-51-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-bromo-hex-2-enoyl chloride
• 英文别名: 2-bromohex-2-enoyl chloride；2-Bromohex-2-enoyl chloride
• CAS: 727425-51-6
• 化学式: C₆H₈BrClO
• 分子量: 211.486
• InChiKey: VCEYDIBPLKIBTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzylidene-(S)-α-methylbenzylamine 、 2-bromo-hex-2-enoyl chloride 在 二甲基氯化铝 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.17h， 以59%的产率得到(1'S,5R,6R)-3-bromo-5-ethyl-6-phenyl-1-(1'-phenyl-ethyl)-5,6-dihydro-pyridin-2-one
  参考文献：
  名称：

  Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition

  摘要：

  An approach to 3-bromo-4-alkyl-6-aryl-5,6-dihydropyridin-2-ones and 3 -bromo-5-ethyl-6-aryl-5,6-dihydropyridin-2-ones starting from beta,gamma-unsaturated alpha-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N-allyl-aziridines or 3-amino-substituted 5,6-dihydropyridin-2-ones, depending on the substituents on the six-membered ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.021
• 作为产物：
  描述：

  反式-2-己烯酸 在 哌啶 、 氯化亚砜 、 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-bromo-hex-2-enoyl chloride
  参考文献：
  名称：

  Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition

  摘要：

  An approach to 3-bromo-4-alkyl-6-aryl-5,6-dihydropyridin-2-ones and 3 -bromo-5-ethyl-6-aryl-5,6-dihydropyridin-2-ones starting from beta,gamma-unsaturated alpha-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N-allyl-aziridines or 3-amino-substituted 5,6-dihydropyridin-2-ones, depending on the substituents on the six-membered ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.021

文献信息

• α-Bromo-β,γ-unsaturated ketenes for the synthesis of α-benzylamino-β,γ-unsaturated acids
  作者：Giuliana Cardillo、Serena Fabbroni、Luca Gentilucci、Rossana Perciaccante、Alessandra Tolomelli

  DOI：10.1016/j.tetasy.2003.12.029

  日期：2004.2

  The synthesis of α-benzylamino-β,γ-unsaturated acids has been developed starting from α-bromo-α,β-unsaturated chlorides. Via treatment of the acyl chlorides with (R)-pantolactone in the presence of TEA, the in situ formation of the deconjugated ketenes and their direct transformation into chiral esters was performed. The substitution of bromine with benzylamine, followed by acid hydrolysis, allowed

  从α-溴-α，β-不饱和氯化物开始发展了α-苄氨基-β，γ-不饱和酸的合成。通过在TEA存在下用（R）-泛内酯处理酰氯，原位形成解偶联的烯酮并将其直接转化为手性酯。用苄胺取代溴，然后进行酸水解，可以得到对映异构体富集的α-苄氨基-β，γ-不饱和酸。