diethyl 2-(4'-bromobutyl)(prop-2''-en-1''-yl)propanedioate | 764583-44-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-(4'-bromobutyl)(prop-2''-en-1''-yl)propanedioate
• 英文别名: Diethyl 2-(4-bromobutyl)-2-prop-2-enylpropanedioate
• CAS: 764583-44-0
• 化学式: C₁₄H₂₃BrO₄
• 分子量: 335.238
• InChiKey: JPDAOCPQBVIMPP-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±42.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-(4'-bromobutyl)(prop-2''-en-1''-yl)propanedioate 在 dibromobis(triphenylphosphine)nickel(II) 三乙基铝 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到diethyl (4-bromobutyl)malonate
  参考文献：
  名称：

  Catalytic Deallylation of Allyl- and Diallylmalonates

  摘要：

  Substituted allylmalonates undergo the selective C-C bond cleavage in the presence of triethylaluminum and a catalytic amount of nickel and ruthenium phosphine complexes, resulting in the loss of the allyl moiety and formation of monosubstituted malonates. Comparison of reactivity of the nickel and ruthenium complexes showed that the use of the former is general with respect to the structure of the substituted allylmalonates, and the activity of the latter depended on the substitution pattern of the double bond of the allylic moiety. The smooth deallylation may encourage the use of the allyl group as a protective group for the acidic hydrogen in malonates.

  DOI：

  10.1021/ja047320t
• 作为产物：
  描述：

  二烯丙基丙二酸二乙酯 在 tris(triphenylphosphine)ruthenium(II) chloride 、 三乙基铝 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 36.0h， 生成 diethyl 2-(4'-bromobutyl)(prop-2''-en-1''-yl)propanedioate
  参考文献：
  名称：

  Catalytic Deallylation of Allyl- and Diallylmalonates

  摘要：

  Substituted allylmalonates undergo the selective C-C bond cleavage in the presence of triethylaluminum and a catalytic amount of nickel and ruthenium phosphine complexes, resulting in the loss of the allyl moiety and formation of monosubstituted malonates. Comparison of reactivity of the nickel and ruthenium complexes showed that the use of the former is general with respect to the structure of the substituted allylmalonates, and the activity of the latter depended on the substitution pattern of the double bond of the allylic moiety. The smooth deallylation may encourage the use of the allyl group as a protective group for the acidic hydrogen in malonates.

  DOI：

  10.1021/ja047320t