2-(3-Methyl-but-2-enylidene)-malonic acid | 135788-59-9

• 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: 2-(3-Methyl-but-2-enylidene)-malonic acid
• 英文别名: 2-(3-Methylbut-2-enylidene)propanedioic acid
• CAS: 135788-59-9
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: SIOSTTXQNZDOBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 哌啶 、 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 15.0h， 生成 2-(3-Methyl-but-2-enylidene)-malonic acid
  参考文献：
  名称：

  Mechanism of cyclocondensation of isoprenoid acyclic ?,?-enals with monoethyl malonate under the conditions of the Knoevenagel reaction

  摘要：

  It was shown that the formation of the di- and trisubstituted derivatives of 1.3-cyclohexadiene-1-carboxylic acid during the condensation of 3-methyl-2-butenal, citral, and farnesal with monoethyl malonate in the presence of secondary amines takes place through the enamines corresponding to these aldehydes, which add to the monoesters of the respective alkenylidenemalonic acids (the "normal" products of the Knoevenagel reaction) by a mechanism of [4 + 2]-cycloaddition. The free carboxyl group in the dienophile is required for the spontaneous transformation of the intermediate [4 + 2]-cycloadducts into the derivatives of cyclohexadiene-1-carboxylic acid in which the catalyst of the process (the secondary amine) is regenerated.

  DOI：

  10.1007/bf00961358