ethyl 6-methyl-2-(ethoxycarbonyl)hept-2-enoate

• 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: ethyl 6-methyl-2-(ethoxycarbonyl)hept-2-enoate
• 英文别名: Diethyl 2-(4-methylpentylidene)propanedioate
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: BKGBSEQEEAMNAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  ethyl 6-methyl-2-(ethoxycarbonyl)hept-2-enoate 在 sodium hydroxide 作用下， 反应 1.0h， 以30%的产率得到6-methyl-2-carboxyhept-2-enoic acid
  参考文献：
  名称：

  Inhibitors of Thermus thermophilus Isopropylmalate Dehydrogenase

  摘要：

  In an attempt to use mechanism-based design for the discovery of inhibitors of the isopropylmalate dehydrogenase from T. thermophilus, we have prepared and studied a number of potential mimics for an intermediate in the oxidative decarboxylation of isopropyl malate, the enol or enolate of alpha-ketoisocaproate. Because hydroxamate and dicarboxylate enolate mimics are strong, uncompetitive inhibitors of the enzyme and vinyl fluoride enol mimics are weak, competitive inhibitors, it is suggested that the reaction involves the enolate. The uncompetitive inhibition by a number of anionic compounds suggests, in combination with previous studies in other laboratories, that they mimic the enolate product of the decarboxylation. An explanation for the potency of the inhibition of IMDH by these compounds is proposed based on the electrostatic interaction of product and cofactor.

  DOI：

  10.1021/jo00088a026
• 作为产物：
  描述：

  4-甲基戊醛 、 丙二酸二乙酯 在 吗啉 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 3.0h， 以64%的产率得到ethyl 6-methyl-2-(ethoxycarbonyl)hept-2-enoate
  参考文献：
  名称：

  Inhibitors of Thermus thermophilus Isopropylmalate Dehydrogenase

  摘要：

  In an attempt to use mechanism-based design for the discovery of inhibitors of the isopropylmalate dehydrogenase from T. thermophilus, we have prepared and studied a number of potential mimics for an intermediate in the oxidative decarboxylation of isopropyl malate, the enol or enolate of alpha-ketoisocaproate. Because hydroxamate and dicarboxylate enolate mimics are strong, uncompetitive inhibitors of the enzyme and vinyl fluoride enol mimics are weak, competitive inhibitors, it is suggested that the reaction involves the enolate. The uncompetitive inhibition by a number of anionic compounds suggests, in combination with previous studies in other laboratories, that they mimic the enolate product of the decarboxylation. An explanation for the potency of the inhibition of IMDH by these compounds is proposed based on the electrostatic interaction of product and cofactor.

  DOI：

  10.1021/jo00088a026

文献信息

• Pirrung Michael C., Han Hyunsoc, Ludwig Richard T., J. Org. Chem., 59 (1994) N 9, S 2430-2436
  作者：Pirrung Michael C., Han Hyunsoc, Ludwig Richard T.

  DOI：——

  日期：——
• Inhibitors of Thermus thermophilus Isopropylmalate Dehydrogenase
  作者：Michael C. Pirrung、Hyunsoo Han、Richard T. Ludwig

  DOI：10.1021/jo00088a026

  日期：1994.5

  In an attempt to use mechanism-based design for the discovery of inhibitors of the isopropylmalate dehydrogenase from T. thermophilus, we have prepared and studied a number of potential mimics for an intermediate in the oxidative decarboxylation of isopropyl malate, the enol or enolate of alpha-ketoisocaproate. Because hydroxamate and dicarboxylate enolate mimics are strong, uncompetitive inhibitors of the enzyme and vinyl fluoride enol mimics are weak, competitive inhibitors, it is suggested that the reaction involves the enolate. The uncompetitive inhibition by a number of anionic compounds suggests, in combination with previous studies in other laboratories, that they mimic the enolate product of the decarboxylation. An explanation for the potency of the inhibition of IMDH by these compounds is proposed based on the electrostatic interaction of product and cofactor.