Ethyl (3E)-3-methyl-3-heptenoate | 186708-20-3

• 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 (3E)-3-methyl-3-heptenoate
• 英文别名: Ethyl (3e)-3-methyl-3-heptenoate；ethyl (E)-3-methylhept-3-enoate
• CAS: 186708-20-3
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: IWVLGZKEFFQASP-VQHVLOKHSA-N

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 (3E)-3-methyl-3-heptenoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2E)-3-Methyl-2-heptenoic 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：

  2-己酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 氯化亚砜 、 锌 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 Ethyl (3E)-3-methyl-3-heptenoate
  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

文献信息

• [EN] OPTIONALLY CONDENSED DIHYDRO PYRIDINE, DIHYDROPYRIMIDINE AND DIHYDRO PYRANE DERIVATIVES ACTING AS LATE SODIUM CHANNEL BLOCKERS<br/>[FR] DÉRIVÉS DE DIHYDROPYRIDINE, DE DIHYDROPYRIMIDINE ET DE DIHYDROPYRANE FACULTATIVEMENT CONDENSÉS, JOUANT LE RÔLE DE BLOQUEURS TARDIFS DES CANAUX SODIQUES
  申请人：CV THERAPEUTICS INC

  公开号：WO2010002483A1

  公开（公告）日：2010-01-07

  The present invention relates to novel heterocyclic compounds and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula (I): wherein Ql, Q2, R2, R3, R4, R5, and R6 are as described herein. The invention also relates to methods for the preparation of the compounds, and to pharmaceutical compositions containing such compounds.
• 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.