1-<4-(3-Oxobutyl)-phenoxy>-3-tert-butylamino-propan-2-ol | 66422-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-<4-(3-Oxobutyl)-phenoxy>-3-tert-butylamino-propan-2-ol
• 英文别名: (+/-)-1-tert-butylamino-3-(4-(3-oxobutyl)phenoxy)propan-2-ol
• CAS: 66422-66-0
• 化学式: C₁₇H₂₇NO₃
• 分子量: 293.406
• InChiKey: JVMPWILRKCOWEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(4-(3-oxobutyl)phenoxy)methyloxirane 、 叔丁胺 以 水 为溶剂， 反应 24.0h， 以77%的产率得到1-<4-(3-Oxobutyl)-phenoxy>-3-tert-butylamino-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

文献信息

• Lipase resolution of new (±)-3-aryloxy-1-halogenopropan-2-ols: Versatile building blocks for β-adrenergic receptor antagonists
  作者：Maciej Maciejewski、Krzysztof Półtorak、Janina E. Kamińska

  DOI：10.1016/j.molcatb.2009.11.004

  日期：2010.3

  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.