(Z)-6-methyl-4-octenoic acid | 150870-89-6

• 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)-6-methyl-4-octenoic acid
• 英文别名: (Z)-6-methyloct-4-enoic acid
• CAS: 150870-89-6
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: HCBVCTYJDOUPID-XQRVVYSFSA-N

物化性质

• 沸点：
  250.8±9.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-6-methyl-4-octenoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到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 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 (Z)-6-methyl-4-octenoic acid
  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

• An Efficient Synthesis of Natural Tribolure
  作者：Jianmin Shi、Lu Liu、Meng Tang、Tao Zhang、Hongjin Bai、Zhenting Du

  DOI：10.1007/s10600-020-02987-3

  日期：2020.3

  An efficient synthesis of natural tribolure has been achieved through an asymmetric methylation as a key step. Natural tribolure is a mixture of four stereoisomers, so racemic 2-methylbutan-1-ol was used as starting material. After a C5+C4 strategy and then a mixed Evan’s template inductive methylation, the key intermediate was obtained. Finally, the natural product tribolure (4:4:1:1 of stereoisomers, respectively) was obtained in 10 linear steps and in 34.2% overall yield.

  通过不对称甲基化作为关键步骤，实现了天然三醇的有效合成。天然tribolure是四种立体异构体的混合物，因此使用外消旋2-甲基丁-1-醇作为起始原料。经过C5+C4策略，然后混合埃文模板诱导甲基化，得到关键中间体。最后，经过10个线性步骤获得了天然产物tribolure（立体异构体分别为4:4:1:1），总产率为34.2%。
• 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.