(E/Z)-methyl 5-hexadecenoate | 125481-80-3

• 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: (E/Z)-methyl 5-hexadecenoate
• 英文别名: methyl hexadec-5-enoate；5-Hexadecenoic acid methyl ester
• CAS: 125481-80-3
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: IPFUCPILAVBTPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.8±21.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (E/Z)-methyl 5-hexadecenoate 在 四氧化锇 、 甲基叔丁基醚 、 N-甲基吗啉氧化物 、 sodium sulfate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 90.0h， 生成 (5S,6R)-(+)-6-hydroxy-5-hexadecanolide
  参考文献：
  名称：

  Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone

  摘要：

  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.

  DOI：

  10.1002/prac.19973390176
• 作为产物：
  描述：

  5-氧代戊酸甲酯 、 (1-十一烷基)三苯基鏻溴化物 在 正丁基锂 作用下， 生成 (E/Z)-methyl 5-hexadecenoate
  参考文献：
  名称：

  Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

  摘要：

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00011-6

文献信息

• Henkel, Birgitta; Kunath, Annamarie; Schick, Hans, Liebigs Annalen, 1995, # 5, p. 921 - 924
  作者：Henkel, Birgitta、Kunath, Annamarie、Schick, Hans

  DOI：——

  日期：——
• 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.
• Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone
  作者：Braj B. Lohray、S. Venkateswarlu

  DOI：10.1016/s0957-4166(97)00011-6

  日期：1997.2

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.