(R)-1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol | 1222178-11-1

• 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: (R)-1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol
• CAS: 1222178-11-1
• 化学式: C₁₃H₁₉BrO₂
• 分子量: 287.197
• InChiKey: RCQDNLLWUPLEAS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol 、 异丙胺 以 水 为溶剂， 以79%的产率得到(S)-1-isopropylamino-3-(2-isopropyl-5-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  Lipase resolution of new (±)-3-aryloxy-1-halogenopropan-2-ols: Versatile building blocks for β-adrenergic receptor antagonists

  摘要：

  Using two commercial immobilized lipases Lipozyme(R) TL and Novozym(R) 435 effective kinetic resolution of several novel 3-aryloxy-1-halogenopropan-2-ols was achieved by acyl transfer reaction in organic solvents, yielding both enantiomers with 89-99% ee. In preparative resolutions carried out in tert-butyl methyl ether at 25 degrees C with vinyl acetate as acyl donor enantioselectivity ratio E was from 64 to 99. The resolved enantiomers were successfully used as chiral building blocks in the synthesis of new 1-alkylamino-3-aryloxypropan-2-ols, by nucleophilic halogen substitution with isopropylamine and tert-butylamine. The obtained products will be evaluated in vitro as potential new beta-adrenergic receptors antagonists. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.11.004
• 作为产物：
  描述：

  乙酸乙烯酯 、 1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol 在 Candida antarctica B lipase Novozym 435 作用下， 以 甲基叔丁基醚 为溶剂， 反应 48.0h， 以40%的产率得到(R)-1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  Lipase resolution of new (±)-3-aryloxy-1-halogenopropan-2-ols: Versatile building blocks for β-adrenergic receptor antagonists

  摘要：

  Using two commercial immobilized lipases Lipozyme(R) TL and Novozym(R) 435 effective kinetic resolution of several novel 3-aryloxy-1-halogenopropan-2-ols was achieved by acyl transfer reaction in organic solvents, yielding both enantiomers with 89-99% ee. In preparative resolutions carried out in tert-butyl methyl ether at 25 degrees C with vinyl acetate as acyl donor enantioselectivity ratio E was from 64 to 99. The resolved enantiomers were successfully used as chiral building blocks in the synthesis of new 1-alkylamino-3-aryloxypropan-2-ols, by nucleophilic halogen substitution with isopropylamine and tert-butylamine. The obtained products will be evaluated in vitro as potential new beta-adrenergic receptors antagonists. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.11.004