ethyl (1'Z)-4-methyl-6-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-cyclohexadiene-1-carboxylate | 135788-40-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (1'Z)-4-methyl-6-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-cyclohexadiene-1-carboxylate
• CAS: 135788-40-8
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: JIJBGGUOZXTLKJ-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  monoethyl citrylidenemalonate 、 3-methyl-1-(N-piperidino)-1,3-butadiene 以 苯 为溶剂， 反应 0.17h， 生成 ethyl (1'Z)-4-methyl-6-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-cyclohexadiene-1-carboxylate 、 ethyl (1'E)-4-methyl-6-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-cyclohexadiene-1-carboxylate
  参考文献：
  名称：

  Acyclic isoprenoid 1,3-dieneamines in the Diels-Alder reaction

  摘要：

  The dieneamines obtained from 3-methyl-2-butenal and citral (Ia) and (Ib, c) enter into [4 + 2]-cycloaddition with monoethyl citrylidenemalonate (II) and prenylidenemalonate (III), respectively, forming the esters of substituted 1,3-cyclohexadiene-1-carboxylic acids with side chains of the isoprenoid type. The same or analogous cyclohexadiene can be obtained from "citral dieneamine" (Ib, c) and typical dienophiles (methyl acrylate, diethyl fumarate, etc.) in a two-stage path, including the initial production of derivatives of 2-amino-3-cyclohexene-1-carboxylic acid in the Diels-Alder reaction and then elimination of the amino group from the cyclic adducts. The isomeric composition of the mixture of cyclic adducts formed in the reaction of (Ib + Ic) with diethyl fumarate under strictly aprotic conditions correlates with the ratio of the structural isomers with a DELTA-3 and DELTA-3(9) bond (Ib, c) in the "citral dieneamine." In the reaction of the dieneamine with the less reactive methyl acrylate the obtained mixture of cyclic adducts contains a significantly larger fraction of the isomer corresponding to the minor DELTA-3(9) isomer of the dieneamine.

  DOI：

  10.1007/bf00961359