(1S,2R,3S,5R)-6,6-Dimethyl-2-phenanthren-9-yl-bicyclo[3.1.1]heptan-3-ol | 136003-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1S,2R,3S,5R)-6,6-Dimethyl-2-phenanthren-9-yl-bicyclo[3.1.1]heptan-3-ol
• CAS: 136003-04-8
• 化学式: C₂₃H₂₄O
• 分子量: 316.443
• InChiKey: NEJCRXQUCYGFCU-VUVCYMEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (1S,2R,3S,5R)-6,6-Dimethyl-2-phenanthren-9-yl-bicyclo[3.1.1]heptan-3-ol 在 zinc borohydride 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 3-Hydroxy-butyric acid (1S,2R,3S,5R)-6,6-dimethyl-2-phenanthren-9-yl-bicyclo[3.1.1]hept-3-yl ester
  参考文献：
  名称：

  New chiral auxiliaries derived from β -pinene: Their use in the asymmetric reduction of β-keto-esters

  摘要：

  3-Ketobutyrates 6, derived from chiral auxiliary alcohols 5 - themselves efficiently prepared from beta-pinene 4 - were reduced with zinc borohydride, giving 3-hydroxybutyrates 7 with 2-70 % de, depending on the nature of aryl group in alcohols 5.

  DOI：

  10.1016/s0957-4166(00)82117-5
• 作为产物：
  描述：

  (1R)-(+)-诺蒎酮 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 、 三氯氧磷 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 33.0h， 生成 (1S,2R,3S,5R)-6,6-Dimethyl-2-phenanthren-9-yl-bicyclo[3.1.1]heptan-3-ol
  参考文献：
  名称：

  New chiral auxiliaries derived from β -pinene: Their use in the asymmetric reduction of β-keto-esters

  摘要：

  3-Ketobutyrates 6, derived from chiral auxiliary alcohols 5 - themselves efficiently prepared from beta-pinene 4 - were reduced with zinc borohydride, giving 3-hydroxybutyrates 7 with 2-70 % de, depending on the nature of aryl group in alcohols 5.

  DOI：

  10.1016/s0957-4166(00)82117-5