(Z)-5-Oxo-hexadec-12-enoic acid methyl ester | 176712-73-5

• 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: (Z)-5-Oxo-hexadec-12-enoic acid methyl ester
• CAS: 176712-73-5
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: LINYTTDLHBDWQI-WAYWQWQTSA-N

反应信息

• 作为反应物：
  描述：

  (Z)-5-Oxo-hexadec-12-enoic acid methyl ester 在 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 ((Z)-6-Undec-7-enyl)-tetrahydro-pyran-2-one
  参考文献：
  名称：

  New mimics of the acetate function in pheromone-based attraction

  摘要：

  Several analogues of (Z)-8-dodecenyl acetate (1a), the major pheromone component of the Oriental fruit moth, Cydia molesta, with chloroformate and lactone functional groups in place of the acetate moiety, were synthesized and investigated for their biological activity at four evaluation levels, i.e. by electroantennography (EAG), electrosensillography (ESG), short-range sexual stimulation and activation in the flight-tunnel. We found very strict requirements on the shape as well as on the electron distribution of the acetate group for a productive interaction with the receptor. The behavioral results showed that, among the analogues investigated, the chloroformate 1b, alken-4-olide 2a and also dodecyl acetate (1c) possess significant (60-85%) inhibitory activities. Based on electrophysiological evidence demonstrating that (i) only 1b is competing with the major pheromone component la for the same receptor sites on the male antennal sensilla, (ii) 1c elicits moderate EAG but no ESG responses and (iii) 2a does not produce any electrophysiological response at all, three possible inhibitory mechanisms by which these analogues are acting could be distinguished. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00029-6
• 作为产物：
  描述：

  2-((Z)-Dec-6-enyl)-4-ethoxycarbonyl-3-oxo-heptanedioic acid diethyl ester 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 44.0h， 生成 (Z)-5-Oxo-hexadec-12-enoic acid methyl ester
  参考文献：
  名称：

  New mimics of the acetate function in pheromone-based attraction

  摘要：

  Several analogues of (Z)-8-dodecenyl acetate (1a), the major pheromone component of the Oriental fruit moth, Cydia molesta, with chloroformate and lactone functional groups in place of the acetate moiety, were synthesized and investigated for their biological activity at four evaluation levels, i.e. by electroantennography (EAG), electrosensillography (ESG), short-range sexual stimulation and activation in the flight-tunnel. We found very strict requirements on the shape as well as on the electron distribution of the acetate group for a productive interaction with the receptor. The behavioral results showed that, among the analogues investigated, the chloroformate 1b, alken-4-olide 2a and also dodecyl acetate (1c) possess significant (60-85%) inhibitory activities. Based on electrophysiological evidence demonstrating that (i) only 1b is competing with the major pheromone component la for the same receptor sites on the male antennal sensilla, (ii) 1c elicits moderate EAG but no ESG responses and (iii) 2a does not produce any electrophysiological response at all, three possible inhibitory mechanisms by which these analogues are acting could be distinguished. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00029-6