ethyl 2-ethenyl-2-methyl-3-oxobenzenepropanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-ethenyl-2-methyl-3-oxobenzenepropanoate
• 英文别名: ethyl 2-benzoyl-2-methyl-3-butenoate；Ethyl 2-benzoyl-2-methylbut-3-enoate；ethyl 2-benzoyl-2-methylbut-3-enoate
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: QCDNAOAVJAKKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙炔 、 2-甲基-3-氧代-3-苯基丙酸乙酯 在 In(OSO₂CF₃)3 、 3 A molecular sieve 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 以70%的产率得到ethyl 2-ethenyl-2-methyl-3-oxobenzenepropanoate
  参考文献：
  名称：

  Indium Triflate-Catalyzed Vinylation of β-Ketoesters with Acetylene Gas

  摘要：

  An ln(OTf)(3)-Catalyzed addition of a beta-ketoester to acetylene in the presence of molecular sieves produces a alpha-vinylated ketoester in good to excellent yield. The vinylation reaction proceeds without any loss of elements in starting molecules under solvent-free conditions and allows the use of welding-grade acetylene, providing a practical method for synthetic utilization of acetylene gas.

  DOI：

  10.1021/ol051057z

文献信息

• GaCl₃-Promoted Ethenylation of Silylated <i>β</i>-Dicarbonyl Compound with Silylethyne. Synthesis of Ethenylmalonate
  作者：Mieko Arisawa、Kensuke Akamatsu、Masahiko Yamaguchi

  DOI：10.1021/ol015583b

  日期：2001.3.1

  [reaction: see text]. In the presence of GaCl3, silyl enol ethers derived from alpha-substituted beta-ketoesters or malonates are ethenylated at the alpha-carbon atom with trimethylsilylethyne in high yields. Ethenylmalonates can also be synthesized by this method.

  [反应：请参见文字]。在GaCl 3存在下，以高收率将由α-取代的β-酮酸酯或丙二酸酯衍生的甲硅烷基烯醇醚在α-碳原子处用三甲基甲硅烷基乙炔进行乙烯基化。烯丙二酸酯也可以通过该方法合成。
• Indium Triflate-Catalyzed Vinylation of β-Ketoesters with Acetylene Gas
  作者：Masaharu Nakamura、Kohei Endo、Eiichi Nakamura

  DOI：10.1021/ol051057z

  日期：2005.7.1

  An ln(OTf)(3)-Catalyzed addition of a beta-ketoester to acetylene in the presence of molecular sieves produces a alpha-vinylated ketoester in good to excellent yield. The vinylation reaction proceeds without any loss of elements in starting molecules under solvent-free conditions and allows the use of welding-grade acetylene, providing a practical method for synthetic utilization of acetylene gas.