methyl(Z)-5-tetra-decanoate | 28369-26-8

• 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: methyl(Z)-5-tetra-decanoate
• 英文别名: Methyl (Z)-tetradec-5-enoate；cis-5-Tetradecensaeuremethylester；formyl 5Z-tetradecenoate
• CAS: 28369-26-8
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: WAFYJSDEQGSUTH-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  methyl(Z)-5-tetra-decanoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 27.0h， 生成 (Z)-5-十四碳烯-1-醇乙酸酯
  参考文献：
  名称：

  Kelkar, S. V.; Reddy, G. Bhaskar; Kulkarni, G. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 980 - 981

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯-4-十三碳炔 在 Lindlar's catalyst 作用下， 生成 methyl(Z)-5-tetra-decanoate
  参考文献：
  名称：

  2-(E)-nonen-1-ol: Male attractant for chafersAnomala vitis Fabr. andA. dubia Scop. (Coleoptera: Scarabaeidae)

  摘要：

  Traps baited with 2-(E)-nonen-1-ol alone or in combination with other compounds caught large numbers of males of both the vine chafer, Anomala vitis Fabr. and the margined vine chafer, A. dubia Scop. (Coleoptera: Scarabaeidae), vineyard and orchard pests. In a dosage test, the largest numbers were caught by traps baited with 10 mg of 2-(E)-nonen-1-ol, which was the highest dosage tested. This is the first report on male attractants for chafer species occurring in Europe.

  DOI：

  10.1007/bf02036185

文献信息

• Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone
  作者：B. Henkel、A. Kunath、Hans Schick

  DOI：10.1002/prac.19973390176

  日期：——

  Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysis of these esters followed by lactonization. Pancreatin-catalyzed lactonization of the dihydroxy esters rac-4 afforded enantiomerically enriched hydroxy lactones ent-5, five of which were obtained enantiomerically pure by recrystallization. Acetylation of the 6-hydroxyalkan-5-olides rac-5 by vinyl acetate catalyzed by the lipase SP 526 provided enantiomerically enriched 6-acetoxyalkan-5-olides 6 with an enantiomeric excess of more than 90% in nine cases. These compounds are known as mosquito oviposition attractant pheromone (6h) or its homologues.
• CASSIDY, D. M.;PRATT, D. A.;TAYLOR, R.;ALBERTI, K. G. M. M.;LAKER, M. F., J. CHROMATOGR. BIOMED. APPL., 491,(1989) N, C. 1-13
  作者：CASSIDY, D. M.、PRATT, D. A.、TAYLOR, R.、ALBERTI, K. G. M. M.、LAKER, M. F.

  DOI：——

  日期：——
• Kelkar, S. V.; Reddy, G. Bhaskar; Kulkarni, G. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 980 - 981
  作者：Kelkar, S. V.、Reddy, G. Bhaskar、Kulkarni, G. H.

  DOI：——

  日期：——
• 2-(E)-nonen-1-ol: Male attractant for chafersAnomala vitis Fabr. andA. dubia Scop. (Coleoptera: Scarabaeidae)
  作者：Miklós Tóth、Walter Soares Leal、István Szarukán、Mátyás Lesznyák、Gábor Szöcs

  DOI：10.1007/bf02036185

  日期：1994.10

  Traps baited with 2-(E)-nonen-1-ol alone or in combination with other compounds caught large numbers of males of both the vine chafer, Anomala vitis Fabr. and the margined vine chafer, A. dubia Scop. (Coleoptera: Scarabaeidae), vineyard and orchard pests. In a dosage test, the largest numbers were caught by traps baited with 10 mg of 2-(E)-nonen-1-ol, which was the highest dosage tested. This is the first report on male attractants for chafer species occurring in Europe.