ethyl 6-(2'-methyl-1'-propenyl)-4-methyl-1,3-cyclohexadienecarboxylate | 135788-52-2

• 英文名称: ethyl 6-(2'-methyl-1'-propenyl)-4-methyl-1,3-cyclohexadienecarboxylate
• 英文别名: ethyl (+)-4-methyl-6-(2-methyl-1-propenyl)-1,3-cyclohexadienecarboxylate；4-Methyl-6-(2-methyl-propenyl)-cyclohexa-1,3-dienecarboxylic acid ethyl ester
• CAS: 135788-52-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: ZGBGPZUJHDVPSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-(2'-methyl-1'-propenyl)-4-methyl-1,3-cyclohexadienecarboxylate 、 丁炔二酸二乙酯 反应 3.0h， 以60%的产率得到triethyl 4-methylbenzene-1,2,3-tricarboxylate
  参考文献：
  名称：

  Formation of derivatives of 1,3-cyclohexadienecarboxylic acid from acyclic isoprenoid ?,?-enals and monoethyl malonate by the Knoevenagel reaction

  摘要：

  DOI：

  10.1007/bf00959577
• 作为产物：
  描述：

  3-methyl-1-(N-piperidino)-1,3-butadiene 在 盐酸 、 氢氧化钾 作用下， 以 苯 为溶剂， 反应 241.0h， 生成 ethyl 6-(2'-methyl-1'-propenyl)-4-methyl-1,3-cyclohexadienecarboxylate
  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

文献信息

• Catalytic asymmetric synthesis of 6-substituted derivatives of 1,3-cyclohexadienecarboxylic acid
  作者：A. G. Nigmatov、E. P. Serebryakov

  DOI：10.1007/bf00700021

  日期：1993.1