(R)-2-methyl-3-chloro-2-cyclohexen-1-ol | 1188268-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-methyl-3-chloro-2-cyclohexen-1-ol
• 英文别名: (1R)-3-chloro-2-methylcyclohex-2-en-1-ol
• CAS: 1188268-25-8
• 化学式: C₇H₁₁ClO
• 分子量: 146.617
• InChiKey: RNJYVOCTEHJXME-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-3-chloro-2-cyclohexen-1-ol 、 乙酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Highly Enantioselective and Regioselective Carbonyl Reduction of Cyclic α,β-Unsaturated Ketones Using TarB-NO₂ and Sodium Borohydride

  摘要：

  Asymmetric 1,2-reduction of alpha,beta-unsaturated ketones using TarB-NO2 and NaBH4 is reported. Simple cycloalkenones give products in low enantiomeric excess. However, cycloalkenones with alpha-substituents, such as halides, alkyl, and aryl, have been enantioselectively reduced with this system to yield chiral allylic alcohols in enantiomeric excess up to 99%. The starting materials for TarB-NO2 are inexpensive, and the boronic acid can be easily recovered in high yield by a simple acid extraction.

  DOI：

  10.1021/ol901677b
• 作为产物：
  描述：

  3-氯-2-甲基环己-2-烯-1-酮 在 sodium tetrahydroborate 、 3-硝基苯硼酸L-酒石酸酯 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-2-methyl-3-chloro-2-cyclohexen-1-ol 、 (S)-2-methyl-3-chloro-2-cyclohexen-1-ol
  参考文献：
  名称：

  Highly Enantioselective and Regioselective Carbonyl Reduction of Cyclic α,β-Unsaturated Ketones Using TarB-NO₂ and Sodium Borohydride

  摘要：

  Asymmetric 1,2-reduction of alpha,beta-unsaturated ketones using TarB-NO2 and NaBH4 is reported. Simple cycloalkenones give products in low enantiomeric excess. However, cycloalkenones with alpha-substituents, such as halides, alkyl, and aryl, have been enantioselectively reduced with this system to yield chiral allylic alcohols in enantiomeric excess up to 99%. The starting materials for TarB-NO2 are inexpensive, and the boronic acid can be easily recovered in high yield by a simple acid extraction.

  DOI：

  10.1021/ol901677b