methyl (Z)-5-hexadecenoic aci | 163562-81-0

• 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-hexadecenoic aci
• 英文别名: Methylcis-5-hexadecenoate；methyl (Z)-hexadec-5-enoate
• CAS: 163562-81-0
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: IPFUCPILAVBTPZ-SEYXRHQNSA-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：

  methyl (Z)-5-hexadecenoic aci 在 ruthenium trichloride 、 sodium periodate 、 四氧化锇 、 氯化亚砜 、 N-甲基吗啉氧化物 作用下， 以 吡啶 、 四氯化碳 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Lohray, Braj B.; Rao, B. Srinivas; Baskaran, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 3, p. 209 - 218

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 (Z)-Hexadec-5-enoic Acid 在 三氟化硼 作用下， 生成 methyl (Z)-5-hexadecenoic aci
  参考文献：
  名称：

  Production of (5R,6S)-6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone, from the Seed Oil of the Summer Cypress Plant, Kochia scoparia (Chenopodiaceae)

  摘要：

  The oviposition pheromone for the pathogen-vectoring mosquitoes in the genus Culex (Diptera: Culicidae), that is, (5R,GS)-6-acetoxy-5-hexadecanolide, is efficiently synthesized, in admixture with the inactive (5S,6R) enantiomer (similar to 33% w/w), from the fixed oil extracted from the seeds of the summer cypress plant, Kochia scoparia (Chenopodiaceae), cultivated on an industrial scale. Oviposition bioassays using gravid females of Culex quinquefasciatus, a vector of filariasis in human beings, showed that the product was attractive, with activity comparable to that of a pure synthetic sample containing the same amount of the active enantiomer. Production of the pheromone in the form of a biologically active crude material via a cheap and renewable plant suitable for development as a new industrial. crop provides the basis for control of Cx. quinquefasciatus and other congeneric vectors of pathogens in resource-poor areas of the world.

  DOI：

  10.1021/jf990294b

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.
• Lohray, Braj B.; Rao, B. Srinivas; Baskaran, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 3, p. 209 - 218
  作者：Lohray, Braj B.、Rao, B. Srinivas、Baskaran、Venkateswarlu、Bhushan

  DOI：——

  日期：——
• Production of (5<i>R</i>,6<i>S</i>)-6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone, from the Seed Oil of the Summer Cypress Plant, <i>Kochia scoparia </i>(Chenopodiaceae)
  作者：Timothy O. Olagbemiro、Michael A. Birkett、A. Jennifer Mordue (Lunt、John A. Pickett

  DOI：10.1021/jf990294b

  日期：1999.8.1

  The oviposition pheromone for the pathogen-vectoring mosquitoes in the genus Culex (Diptera: Culicidae), that is, (5R,GS)-6-acetoxy-5-hexadecanolide, is efficiently synthesized, in admixture with the inactive (5S,6R) enantiomer (similar to 33% w/w), from the fixed oil extracted from the seeds of the summer cypress plant, Kochia scoparia (Chenopodiaceae), cultivated on an industrial scale. Oviposition bioassays using gravid females of Culex quinquefasciatus, a vector of filariasis in human beings, showed that the product was attractive, with activity comparable to that of a pure synthetic sample containing the same amount of the active enantiomer. Production of the pheromone in the form of a biologically active crude material via a cheap and renewable plant suitable for development as a new industrial. crop provides the basis for control of Cx. quinquefasciatus and other congeneric vectors of pathogens in resource-poor areas of the world.