(S)-1-chloro-3-(2-isopropyl-5-methylphenoxy)prop-2-yl acetate | 1222178-14-4

• 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: (S)-1-chloro-3-(2-isopropyl-5-methylphenoxy)prop-2-yl acetate
• CAS: 1222178-14-4
• 化学式: C₁₅H₂₁ClO₃
• 分子量: 284.783
• InChiKey: KWBPXHXPYOSBFO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-chloro-3-(2-isopropyl-5-methylphenoxy)prop-2-yl acetate 、 异丙胺 在 sodium hydroxide 作用下， 以 水 为溶剂， 以98%的产率得到(R)-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-chloro-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol 在 Thermomyces lanuginosus lipase Lipozyme TL 作用下， 以 甲基叔丁基醚 为溶剂， 反应 48.0h， 以36%的产率得到(R)-1-chloro-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