(-)-(S)-[(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl](2''-pyridyl)methanol | 180729-59-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(S)-[(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl](2''-pyridyl)methanol
• 英文别名: (S)-[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-pyridin-2-ylmethanol
• CAS: 180729-59-3
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: JLNQDXUUYNTREV-HOSILWTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(S)-[(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl](2''-pyridyl)methanol 在 间氯过氧苯甲酸 、 二甲氨基甲酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (R)-((1S,2S,5R)-2-isopropyl-5-methyl-1-cyclohexyl)-(6'-cyano-2'-pyridyl)methanol
  参考文献：
  名称：

  Enantioselective Allylic Substitutions Catalyzed by [(Hydroxyalkyl)pyridinooxazoline]- and [(Alkoxyalkyl)pyridinooxazoline]palladium Complexes

  摘要：

  Highly enantioselective (up to >99% eel palladium-catalyzed substitution of rac-3-diphenyl-2-propenyl acetate with dimethyl malonate as nucleophile was achieved using 2-(1-hydroxyalkyl)-6-(4,5-dihydro-2-oxazolyl)pyridines and 2-(1-alkoxyalkyl)-6-(4,5-dihydro-2-oxazolyl)pyridines as ligands for palladium. The selectivity was found to be highly dependent on the nature of the substituents on the ligand and on the relative configuration of the two stereogenic centers present in the ligand. The results are discussed in terms of the conformation of the ligands in the intermediate pi-allylpalladium complexes.

  DOI：

  10.1021/jo961490+
• 作为产物：
  描述：

  (1S,2S,5R)-新薄荷基丁酯 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (-)-(S)-[(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl](2''-pyridyl)methanol
  参考文献：
  名称：

  来自手性吡啶醇的吡啶基亚膦酸酯和吡啶基亚磷酸酯——模块化方法

  摘要：

  手性芳基化吡啶醇、吡啶基亚膦酸酯和吡啶基亚磷酸酯是通过 Suzuki 芳基化和/或 O-官能化与氯二芳基膦或氯二芳基亚磷酸酯 o 制备的。

  DOI：

  10.1002/ejoc.200300368

文献信息

• Synthesis and characterisation of a suite of four chiral pyridyl alcohols derived from (−)-menthol
  作者：Desmond Cunningham、Eva T. Gallagher、David H. Grayson、Patrick J. McArdle、Christina B. Storey、Deborah J. Wilcock

  DOI：10.1039/b205872n

  日期：——

  Reaction of menthylmagnesium chloride with pyridine-2-carbaldehyde gives a mixture of four isomeric chiral menthyl- and neomenthyl-substituted pyridylcarbinols which were fully characterised by a combination of spectroscopic and X-ray crystallographic methods. All of these alcohols catalyse the addition of diethylzinc to benzaldehyde, but with disappointing enantioselectivities.

  薄荷基氯化镁与吡啶-2-甲醛反应，得到四种异构手性薄荷基和新薄荷基取代的吡啶基甲醇的混合物，并通过光谱和 X 射线晶体学方法的组合对其进行了充分表征。所有这些醇都催化二乙基锌与苯甲醛的加成，但对映选择性令人失望。
• Novel 2-(hydroxyalkyl)pyridines derived from the chiral pool
  作者：Hans Adolfsson、Kerstin Nordström、Kenneth Wärnmark、Christina Moberg

  DOI：10.1016/0957-4166(96)00237-6

  日期：1996.7

  Two diastereomeric 2-(1-hydroxyalkyl)pyridines were conveniently prepared starting from (-)-menthol. The pyridylalcohols were subsequently allowed to react with phosphorus oxychloride to yield, in one step, C-3-symmetric tripodal tripyridine ligands. Copyright (C) 1996 Elsevier Science Ltd