Ethyl (3Z)-3-methyl-3-heptenoate | 177024-61-2

• 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 (3Z)-3-methyl-3-heptenoate
• 英文别名: ethyl (Z)-3-methylhept-3-enoate
• CAS: 177024-61-2
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: IWVLGZKEFFQASP-CLFYSBASSA-N

物化性质

• 沸点：
  211.8±9.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl (3Z)-3-methyl-3-heptenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以55%的产率得到3-methyl-(3Z)-heptenoic acid
  参考文献：
  名称：

  用于烯烃昆虫信息素的立体控制合成的通用且方便的协议。

  摘要：

  2,4-二烯酸烷基酯的Horner-Emmons合成与在复杂的L.Cr（CO）3催化剂（L = 3CO或芳烃）上的氢化反应相结合，提供了一种通用的，立体控制的且操作简单的方法（Z）-二取代的（Z）-三取代的（E）-三取代的烯烃和跳过的（Z，Z）-二取代的二烯烃具有均聚物类型的功能。该方案，有时还辅以酶促水解，已成功地应用于家具地毯甲虫，干豆甲虫，生锈的谷物甲虫，方颈谷物甲虫和小径的构型纯（gp>或= 98％）信息素的合成信息素模仿地下白蚁。

  DOI：

  10.1016/0968-0896(96)00016-8
• 作为产物：
  描述：

  (2E,4E)-3-Methyl-hepta-2,4-dienoic acid ethyl ester 在 氢气 、 六羰基铬 作用下， 以 正己烷 为溶剂， 180.0 ℃ 、8.11 MPa 条件下， 反应 3.0h， 以60%的产率得到Ethyl (3Z)-3-methyl-3-heptenoate
  参考文献：
  名称：

  用于烯烃昆虫信息素的立体控制合成的通用且方便的协议。

  摘要：

  2,4-二烯酸烷基酯的Horner-Emmons合成与在复杂的L.Cr（CO）3催化剂（L = 3CO或芳烃）上的氢化反应相结合，提供了一种通用的，立体控制的且操作简单的方法（Z）-二取代的（Z）-三取代的（E）-三取代的烯烃和跳过的（Z，Z）-二取代的二烯烃具有均聚物类型的功能。该方案，有时还辅以酶促水解，已成功地应用于家具地毯甲虫，干豆甲虫，生锈的谷物甲虫，方颈谷物甲虫和小径的构型纯（gp>或= 98％）信息素的合成信息素模仿地下白蚁。

  DOI：

  10.1016/0968-0896(96)00016-8

文献信息

• Identification of sex pheromones from cowpea weevil,Callosobruchus maculatus, and related studies withC. analis (coleoptera: Bruchidae)
  作者：Thomas W. Phillips、Joel K. Phillips、Francis X. Webster、Rong Tang、Wendell E. Burkholder

  DOI：10.1007/bf02029543

  日期：1996.12

  Female cowpea weevils, Callosobruchus maculatus, produce a sex pheromone that elicits orientation and sexual behavior in males. Bioassay-directed isolation of the sex pheromone was conducted and compounds in the active fraction were identified and synthesized. Volatiles were collected from individual virgin females by adsorption on filter paper discs and hexane extraction. A bioassay was used in which the locomotory response of single males in glass vials was recorded upon exposure to treatments or controls. Crude extracts were subjected to silica gel column chromatography with solvents of increasing polarity; all activity eluted with methanol. Activity in the highly polar methanol fraction suggested a carboxylic acid or a compound with multiple polar functionality. Acid-base partitioning of the crude extract isolated all activity in the acid fraction, confirming that the pheromone was a carboxylic acid. The acid fraction was further fractionated by preparative GC with a Carbowax column. The most active GC fraction contained the following five 8-carbon acids identified by GC-MS and comparison with synthetic candidates: 3-methyleneheptanoic acid, (Z)-3-methyl-3-heptenoic acid, (E)-3-methyl-3-heptenoic acid, (Z)-3-methyl-2-heptenoic acid, and (E)-3-methyl-2-heptenoic acid. Each of the synthetic acids was active individually for males, and combinations of two or more of the acid pheromones had an additive effect. Upwind flight responses to natural and synthetic pheromones were observed in a flight tunnel. (Z)-3-Methyl-2-heptenoic acid was previously identified as the sex pheromone for the related C. analis, but this and the other four acid pheromones from C. maculatus were inactive for male C. analis. There was no cross-attraction between C. maculatus and C. analis in reciprocal studies using extracted volatiles from females of both species, GCMS analysis of C. analis female volatiles failed to detect any of the C. maculatus compounds but did find an unidentified C-8 acid with a GC retention time different from any of the C. maculatus pheromones.