3-亚甲基庚酸乙酯 | 136578-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-亚甲基庚酸乙酯
• 英文名称: ethyl 3-n-butyl-3-butenoate
• 英文别名: Ethyl 3-methyleneheptanoate；ethyl 3-methylideneheptanoate
• CAS: 136578-49-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: RJYSICKNNUNHQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  7
• 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：

  3-亚甲基庚酸乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-methylideneheptanoic acid
  参考文献：
  名称：

  Identification of sex pheromones from cowpea weevil,Callosobruchus maculatus, and related studies withC. analis (coleoptera: Bruchidae)

  摘要：

  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.

  DOI：

  10.1007/bf02029543
• 作为产物：
  描述：

  1-trimethylsilyl-2-hexanone 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-亚甲基庚酸乙酯
  参考文献：
  名称：

  由三甲基甲硅烷基甲基酮和酰基硅烷选择性地形成烯烃

  摘要：

  容易得自酰氯的三甲基甲硅烷基甲基酮经过Reformatsky-Peterson反应序列产生3-链烯酸酯区域选择性。但是，酰基硅烷会与烯醇锌酸锌或三甲基甲硅烷基甲基氯化镁反应生成相应的叔醇，根据其结构，叔醇会自发地进行消除或布鲁克重排-彼得森烯化序列。这些反应允许选择性地形成乙烯基硅烷。

  DOI：

  10.1016/0022-328x(91)86327-m

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.
• Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes
  作者：Alois Fu¨rstner、Gerlinde Kollegger、Hans Weidmann

  DOI：10.1016/0022-328x(91)86327-m

  日期：1991.8

  Trimethylsilylmethyl ketones, readily from acyl chlorides, undergo a Reformatsky—Peterson reaction sequence to give 3-alkenoates regioselectivity. Acylsilanes, however, react with either zinc ester enolates or trimethylsilymethylmagnesium chloride to give the corresponding tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement—Peterson

  容易得自酰氯的三甲基甲硅烷基甲基酮经过Reformatsky-Peterson反应序列产生3-链烯酸酯区域选择性。但是，酰基硅烷会与烯醇锌酸锌或三甲基甲硅烷基甲基氯化镁反应生成相应的叔醇，根据其结构，叔醇会自发地进行消除或布鲁克重排-彼得森烯化序列。这些反应允许选择性地形成乙烯基硅烷。