(2E,4RS,6RS)-2,4,6-trimethyltetracos-2-enoic acid

• 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: (2E,4RS,6RS)-2,4,6-trimethyltetracos-2-enoic acid
• 英文别名: (E)-2,4,6-trimethyltetracos-2-enoic acid
• 化学式: C₂₇H₅₂O₂
• 分子量: 408.709
• InChiKey: SJZUAPDAKBPNQS-WNAAXNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  29
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4RS,6RS)-2,4,6-trimethyltetracos-2-enoic acid 、 碘甲烷 在 四丁基氢氧化铵 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以97%的产率得到methyl (2E,4RS,6RS)-2,4,6-trimethyltetracos-2-enoate
  参考文献：
  名称：

  Synthesis of a derivative of racemic 3-hydroxy-2,4,6-trimethyltetracosanoic (mycolipanolic) acid and racemic 2,4,6-trimethyltetracos-2-enoic (mycolipenic) acid

  摘要：

  Racemic 2,4-dimethyldocosanol, available from previous studies, was oxidised to the aldehyde using pyridinium chlorochromate. Aldol reaction of 2,4-dimethyldocosanal with methyl propionate afforded racemic methyl 3-hydroxy-2,4,6-trimethyltetracosanoic acid. The hydroxy function was protected as a tert-butyldimethylsilyl ether and the ester functionality hydrolysed to the free acid. Wittig reaction of 2,4-dimethyldocosanal using 1-carboethoxyethylidenetriphenylphosphorane afforded the (E)-stereoisomer following removal of the small quantities of (Z)-isomer by column chromatography. The ethyl ester was hydrolysed to afford racemic 2,4,6-trimethyltetracos-2-enoic acid. These unusual fatty acids are characteristic of Mycobacterium tuberculosis.

  DOI：

  10.1016/0009-3084(96)02571-6
• 作为产物：
  描述：

  (E)-2,4,6-Trimethyl-tetracos-2-enoic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 以72%的产率得到(2E,4RS,6RS)-2,4,6-trimethyltetracos-2-enoic acid
  参考文献：
  名称：

  Synthesis of a derivative of racemic 3-hydroxy-2,4,6-trimethyltetracosanoic (mycolipanolic) acid and racemic 2,4,6-trimethyltetracos-2-enoic (mycolipenic) acid

  摘要：

  Racemic 2,4-dimethyldocosanol, available from previous studies, was oxidised to the aldehyde using pyridinium chlorochromate. Aldol reaction of 2,4-dimethyldocosanal with methyl propionate afforded racemic methyl 3-hydroxy-2,4,6-trimethyltetracosanoic acid. The hydroxy function was protected as a tert-butyldimethylsilyl ether and the ester functionality hydrolysed to the free acid. Wittig reaction of 2,4-dimethyldocosanal using 1-carboethoxyethylidenetriphenylphosphorane afforded the (E)-stereoisomer following removal of the small quantities of (Z)-isomer by column chromatography. The ethyl ester was hydrolysed to afford racemic 2,4,6-trimethyltetracos-2-enoic acid. These unusual fatty acids are characteristic of Mycobacterium tuberculosis.

  DOI：

  10.1016/0009-3084(96)02571-6

文献信息

• US4514287A
  申请人：——

  公开号：US4514287A

  公开（公告）日：1985-04-30
• Synthesis of a derivative of racemic 3-hydroxy-2,4,6-trimethyltetracosanoic (mycolipanolic) acid and racemic 2,4,6-trimethyltetracos-2-enoic (mycolipenic) acid
  作者：Paul A. Wallace、David E. Minnikin

  DOI：10.1016/0009-3084(96)02571-6

  日期：1996.9

  Racemic 2,4-dimethyldocosanol, available from previous studies, was oxidised to the aldehyde using pyridinium chlorochromate. Aldol reaction of 2,4-dimethyldocosanal with methyl propionate afforded racemic methyl 3-hydroxy-2,4,6-trimethyltetracosanoic acid. The hydroxy function was protected as a tert-butyldimethylsilyl ether and the ester functionality hydrolysed to the free acid. Wittig reaction of 2,4-dimethyldocosanal using 1-carboethoxyethylidenetriphenylphosphorane afforded the (E)-stereoisomer following removal of the small quantities of (Z)-isomer by column chromatography. The ethyl ester was hydrolysed to afford racemic 2,4,6-trimethyltetracos-2-enoic acid. These unusual fatty acids are characteristic of Mycobacterium tuberculosis.