4-溴-2,4-二甲基-1-戊烯-3-酮 | 136839-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-溴-2,4-二甲基-1-戊烯-3-酮
• 英文名称: 4-bromo-2,4-dimethyl-1-penten-3-one
• 英文别名: 4-Bromo-2,4-dimethylpent-1-en-3-one
• CAS: 136839-81-1
• 化学式: C₇H₁₁BrO
• 分子量: 191.068
• InChiKey: WUVFQUOTZCNDOF-UHFFFAOYSA-N

物化性质

• 沸点：
  188.2±23.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  4-溴-2,4-二甲基-1-戊烯-3-酮 以 乙醚 为溶剂， 反应 1.0h， 生成 2,4-二甲基-3-己酮
  参考文献：
  名称：

  Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents

  摘要：

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.

  DOI：

  10.1021/jo00024a014
• 作为产物：
  描述：

  2,4-二溴-2,4-二甲基-3-戊酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以45%的产率得到4-溴-2,4-二甲基-1-戊烯-3-酮
  参考文献：
  名称：

  Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents

  摘要：

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.

  DOI：

  10.1021/jo00024a014

文献信息

• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 2. Reactions with malonate anion. Concerning the mechanism of the Favorskii rearrangement
  作者：Thomas R. Barbee、Hedeel Guy、Mary Jane Heeg、Kim F. Albizati

  DOI：10.1021/jo00024a015

  日期：1991.11

  The scope and limiations of the reaction of alpha'-nucleofuge alpha,beta-unsaturated ketones with sodium dimethyl malonate has been studied systematically. The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction. In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold. Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.