ethyl (4Z)-6-methyloct-4-enoate | 150870-88-5

• 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: ethyl (4Z)-6-methyloct-4-enoate
• 英文别名: ethyl (Z)-6-methyl-4-octenoate；Ethyl (4z)-6-methyloct-4-enoate；ethyl (Z)-6-methyloct-4-enoate
• CAS: 150870-88-5
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: WIDBRKDALFFOQL-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  ethyl (4Z)-6-methyloct-4-enoate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 6-甲基辛酸
  参考文献：
  名称：

  Isolation and synthesis of caprolactins A and B, new caprolactams from a marine bacterium

  摘要：

  Two new caprolactams have been isolated from an unidentified Gram-positive bacterium obtained from a deep-ocean sediment sample. Caprolactins A (1) and B (2), which were obtained as an inseparable mixture, are composed of cyclic-L-lysine linked to 7-methyloctanoic acid and 6-methyloctanoic acid, respectively. The structures were proposed using spectroscopic methods and confirmed by synthesis. Both caprolactins A and B are cytotoxic towards human epidermoid carcinoma (KB) cells and human colorectal adenocarcinoma (LoVo) cells and exhibit antiviral activity towards Herpes simplex type II virus.

  DOI：

  10.1016/s0040-4020(01)81825-1
• 作为产物：
  描述：

  2-甲基丁醛 、 <γ-(ethoxycarbonyl)propyl>triphenylphosphonium iodide 在 sodium ethanolate 作用下， 生成 ethyl (4Z)-6-methyloct-4-enoate
  参考文献：
  名称：

  Isolation and synthesis of caprolactins A and B, new caprolactams from a marine bacterium

  摘要：

  Two new caprolactams have been isolated from an unidentified Gram-positive bacterium obtained from a deep-ocean sediment sample. Caprolactins A (1) and B (2), which were obtained as an inseparable mixture, are composed of cyclic-L-lysine linked to 7-methyloctanoic acid and 6-methyloctanoic acid, respectively. The structures were proposed using spectroscopic methods and confirmed by synthesis. Both caprolactins A and B are cytotoxic towards human epidermoid carcinoma (KB) cells and human colorectal adenocarcinoma (LoVo) cells and exhibit antiviral activity towards Herpes simplex type II virus.

  DOI：

  10.1016/s0040-4020(01)81825-1

文献信息

• Fe-catalyzed synthesis of (4Z)-alkenoates
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1134/s1070363217030306

  日期：2017.3

  A new approach to stereoselective synthesis of (4Z)-alkenoates has been developed based on Fecatalyzed cross-coupling of ethyl (4Z)-5-chloropent-4-enoate with the Grignard reagents.
• Isolation and synthesis of caprolactins A and B, new caprolactams from a marine bacterium
  作者：Bradley S. Davidson、Robert W. Schumacher

  DOI：10.1016/s0040-4020(01)81825-1

  日期：1993.7

  Two new caprolactams have been isolated from an unidentified Gram-positive bacterium obtained from a deep-ocean sediment sample. Caprolactins A (1) and B (2), which were obtained as an inseparable mixture, are composed of cyclic-L-lysine linked to 7-methyloctanoic acid and 6-methyloctanoic acid, respectively. The structures were proposed using spectroscopic methods and confirmed by synthesis. Both caprolactins A and B are cytotoxic towards human epidermoid carcinoma (KB) cells and human colorectal adenocarcinoma (LoVo) cells and exhibit antiviral activity towards Herpes simplex type II virus.