2,4-dimethyldocosanol | 98318-53-7

• 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: 2,4-dimethyldocosanol
• 英文别名: (2RS,4RS)-2,4-dimethyldocosanol；optically inactive 2,4-dimethyl-docosan-1-ol；Opt. inakt. 2,4-Dimethyl-docosan-1-ol；2,4-Dimethyldocosan-1-ol；2,4-dimethyldocosan-1-ol
• CAS: 98318-53-7
• 化学式: C₂₄H₅₀O
• 分子量: 354.66
• InChiKey: UVLQXVMWBKTZPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  25.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethyldocosanol 在 aluminum oxide 、 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到(2RS,4RS)-2,4-dimethyldocosanal
  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：

  ethyl 2-methyleicosanoate 在 磷化氢 、 lithium aluminium tetrahydride 、 乙醚 、 碘 、 正丁醇 作用下， 生成 2,4-dimethyldocosanol
  参考文献：
  名称：

  Bailey et al., Journal of the Chemical Society, 1953, p. 3031,3033

  摘要：

  DOI：

文献信息

• Synthesis of (2R; 4R,S)- and (2S; 4R,S)-dimethyldocosanoic acids
  作者：Paul A. Wallace、David E. Minnikin

  DOI：10.1016/0009-3084(94)90019-1

  日期：1994.6

  2,4-Dimethyldocosanoic acid is a major acyl component of 2,3-di-O-acyl-alpha,alpha-trehalose glycolipid antigens isolated from Mycobacterium tuberculosis. Racemic 2,4-dimethyldocosanoic acid has been synthesized and the chiral centre at C-2 resolved as an (R)-(-)-naphthylethylamide. An isomeric mixture of 3,5-dimethylcyclohexan-1-ols was oxidised to isomeric 3,5-dimethylcyclohexan-1-ones. This was subjected to Baeyer-Villiger oxidation to give isomeric 3,5-dimethylcaprolactones. Ring opening under alkaline conditions followed by phase-transfer catalysed esterification gave isomeric methyl 3,5-dimethyl-6-hydroxyhexanoates. Protection of the alcohol with triphenylmethyl chloride followed by lithium aluminium hydride reduction and pyridinium chlorochromate oxidation gave isomeric 3,5-dimethyl-6-triphenylmethyloxyhexanals. Coupling with hexadecyltriphenylphosphonium bromide, followed by trityl deprotection and hydrogenation of the remaining alkene, yielded isomeric 2,4-dimethyldocosanoic acids, which were resolved at C-2 as diastereoisomeric (R)-(-)-naphthylethylamides.
• Bailey et al., Journal of the Chemical Society, 1953, p. 3031,3033
  作者：Bailey et al.

  DOI：——

  日期：——
• 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.