(6E,Z)2,4-dimethyldocos-6-en-1-ol | 160745-02-8

• 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: (6E,Z)2,4-dimethyldocos-6-en-1-ol
• CAS: 160745-02-8
• 化学式: C₂₄H₄₈O
• 分子量: 352.645
• InChiKey: RMMMIEHEFKHZHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  25.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (6E,Z)2,4-dimethyldocos-6-en-1-ol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 重铬酸吡啶 、 草酰氯 、 4 A molecular sieve 、 氢气 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 (2R)-N-2-naphthylethyl-2(2R,4R,S)-dimethyldocosamide
  参考文献：
  名称：

  Synthesis of (2R; 4R,S)- and (2S; 4R,S)-dimethyldocosanoic acids

  摘要：

  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.

  DOI：

  10.1016/0009-3084(94)90019-1
• 作为产物：
  描述：

  3,5-二甲基环己酮 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 4 A molecular sieve 、 四丁基氢氧化铵 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 80.52h， 生成 (6E,Z)2,4-dimethyldocos-6-en-1-ol
  参考文献：
  名称：

  Synthesis of (2R; 4R,S)- and (2S; 4R,S)-dimethyldocosanoic acids

  摘要：

  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.

  DOI：

  10.1016/0009-3084(94)90019-1