(Z)-methyl 7-methyloct-5-enoate | 112375-41-4

• 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)-methyl 7-methyloct-5-enoate
• 英文别名: Methyl (Z)-7-methyloct-5-enoate
• CAS: 112375-41-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: LQWSFKTUPQOUHH-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  (Z)-methyl 7-methyloct-5-enoate 在 palladium on activated charcoal 氢氧化钾 、 氯化亚砜 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 25.0~100.0 ℃ 、101.33 kPa 条件下， 反应 95.5h， 生成 降二氢辣椒碱
  参考文献：
  名称：

  Capsaicinoids: their separation, synthesis, and mutagenicity

  摘要：

  DOI：

  10.1021/jo00240a024
• 作为产物：
  描述：

  5-羟基戊酸甲酯 在 potassium tert-butylate 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 22.58h， 生成 (Z)-methyl 7-methyloct-5-enoate
  参考文献：
  名称：

  Capsaicinoids: their separation, synthesis, and mutagenicity

  摘要：

  DOI：

  10.1021/jo00240a024

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.
• GANNETT, PETER M.;NAGEL, DONALD L.;REILLY, PAM J.;LAWSON, TERENCE;SHARPE,+, J. ORG. CHEM., 53,(1988) N 5, 1064-1071
  作者：GANNETT, PETER M.、NAGEL, DONALD L.、REILLY, PAM J.、LAWSON, TERENCE、SHARPE,+

  DOI：——

  日期：——
• Capsaicinoids: their separation, synthesis, and mutagenicity
  作者：Peter M. Gannett、Donald L. Nagel、Pam J. Reilly、Terence Lawson、Jody Sharpe、Bela Toth

  DOI：10.1021/jo00240a024

  日期：1988.3