(1S)-1-(1'-adamantyl)-2->-1-ethanol | 145238-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (1S)-1-(1'-adamantyl)-2->-1-ethanol
• 英文别名: (1S)-1-(1'-adamantyl)-2-(spiro[1,3-benzodioxole-2,1'-cyclohexane])-1-ethanol；(1S)-1-(1-adamantyl)-2-spiro[1,3-benzodioxole-2,1'-cyclohexane]-4-ylethanol
• CAS: 145238-41-1
• 化学式: C₂₄H₃₂O₃
• 分子量: 368.516
• InChiKey: ZFTDBVJUTQXCOW-DSQUVOCVSA-N

物化性质

• 沸点：
  513.0±29.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-(1'-adamantyl)-2->-1-ethanol 在 盐酸 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 A 77636盐酸盐
  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
• 作为产物：
  描述：

  (1R)-1-(1'-adamantyl)-2-bromo-1-hydroxyethane 在 sodium hydroxide 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 22.5h， 生成 (1S)-1-(1'-adamantyl)-2->-1-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