(S)-1-Adamantan-1-yl-2-chloro-ethanol | 145238-43-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S)-1-Adamantan-1-yl-2-chloro-ethanol
• 英文别名: (1S)-1-(1-adamantyl)-2-chloroethanol
• CAS: 145238-43-3
• 化学式: C₁₂H₁₉ClO
• 分子量: 214.735
• InChiKey: YNHPKJQSNQTRHG-LTMLNTECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-adamantyl chloromethyl ketone 在 proline-derived oxazaborolidine 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-1-Adamantan-1-yl-2-chloro-ethanol 、 (R)-1-Adamantan-1-yl-2-chloro-ethanol
  参考文献：
  名称：

  The enantioselective synthesis of the potent dopamine D1 agonist (1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran (A77636)

  摘要：

  The synthesis of both enantiomers of the title compound is described. The corresponding racemic compound (+/-)-1 was previously shown to be a highly potent and selective dopamine Dl agonist. Key to the synthesis of the enantiomers was the oxazaborolidine-catalyzed asymmetric reduction of the alpha-bromomethyl ketone 12 which led to the optically enriched epoxide 7. An aryllithium addition to the epoxide followed by a diastereospecific cyclization to the isochroman system furnished compound 17, which was deprotected to afford (-)-1 with >99.5% optical purity.

  DOI：

  10.1021/jo00052a025

文献信息

• The enantioselective synthesis of the potent dopamine D1 agonist (1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran (A77636)
  作者：Michael P. DeNinno、Richard J. Perner、Howard E. Morton、Stanley DiDomenico

  DOI：10.1021/jo00052a025

  日期：1992.12

  The synthesis of both enantiomers of the title compound is described. The corresponding racemic compound (+/-)-1 was previously shown to be a highly potent and selective dopamine Dl agonist. Key to the synthesis of the enantiomers was the oxazaborolidine-catalyzed asymmetric reduction of the alpha-bromomethyl ketone 12 which led to the optically enriched epoxide 7. An aryllithium addition to the epoxide followed by a diastereospecific cyclization to the isochroman system furnished compound 17, which was deprotected to afford (-)-1 with >99.5% optical purity.