3-[N-(phenylacetyl)amino]-3-phenyl-1-propanol | 881853-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[N-(phenylacetyl)amino]-3-phenyl-1-propanol
• 英文别名: N-[(1S)-3-hydroxy-1-phenylpropyl]-2-phenylacetamide
• CAS: 881853-41-4
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: FDFZNPCDYVPVRD-INIZCTEOSA-N

物化性质

• 沸点：
  517.1±50.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[N-(phenylacetyl)amino]-3-phenyl-1-propanol 在 盐酸 作用下， 以100%的产率得到(S)-3-氨基-3-苯基-1-丙醇盐酸盐
  参考文献：
  名称：

  Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase

  摘要：

  Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker's yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee > 99%) and > 45% yields for each enantiomer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.022
• 作为产物：
  描述：

  3-氨基-3-苯基-1-丙醇 在 sodium hydroxide 、 phosphate buffer 、 penicillin G acylase immobilized on epoxy-resin 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3-[N-(phenylacetyl)amino]-3-phenyl-1-propanol
  参考文献：
  名称：

  Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase

  摘要：

  Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker's yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee > 99%) and > 45% yields for each enantiomer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.022

文献信息

• Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase
  作者：Nitin W. Fadnavis、Kasiraman R. Radhika、A. Vedamayee Devi

  DOI：10.1016/j.tetasy.2005.12.022

  日期：2006.1

  Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker's yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee > 99%) and > 45% yields for each enantiomer. (c) 2006 Elsevier Ltd. All rights reserved.