(S,S)-2-(2-hydroxyphenyl)-N,N-bis-(1-phenylethyl)acetamide | 543681-06-7

• 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: (S,S)-2-(2-hydroxyphenyl)-N,N-bis-(1-phenylethyl)acetamide
• 英文别名: Benzeneacetamide, 2-hydroxy-N,N-bis[(1S)-1-phenylethyl]-；2-(2-hydroxyphenyl)-N,N-bis[(1S)-1-phenylethyl]acetamide
• CAS: 543681-06-7
• 化学式: C₂₄H₂₅NO₂
• 分子量: 359.468
• InChiKey: JIQWHISDIDOJIJ-OALUTQOASA-N

物化性质

• 沸点：
  545.1±50.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-2-(2-hydroxyphenyl)-N,N-bis-(1-phenylethyl)acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (S,S)-2-{[2-bis(1-phenylethyl)amino]ethyl}phenol
  参考文献：
  名称：

  Munoz-Muniz, Omar; Juaristi, Eusebio, Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3781 - 3785

  摘要：

  DOI：
• 作为产物：
  描述：

  邻羟基苯乙酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (S,S)-2-(2-hydroxyphenyl)-N,N-bis-(1-phenylethyl)acetamide
  参考文献：
  名称：

  Munoz-Muniz, Omar; Juaristi, Eusebio, Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3781 - 3785

  摘要：

  DOI：
• 作为试剂：
  描述：

  (+/-)-1-benzoyl-5-benzyl-3-methyltetrahydropyrimidin-4-one 在 正丁基锂 、 二异丙胺 、 (S,S)-2-(2-hydroxyphenyl)-N,N-bis-(1-phenylethyl)acetamide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (5S)-1-benzoyl-5-benzyl-3-methyltetrahydropyrimidin-4-one 、 (5R)-1-benzoyl-5-benzyl-3-methyltetrahydropyrimidin-4-one
  参考文献：
  名称：

  Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids

  摘要：

  Achiral 1-benzoyl-3-methylperhydropyrimidin-4-one (1) was deemed a useful, potential precursor for the enantioselective synthesis of alpha-substituted beta-amino acids. Pyrimidinone 1 was prepared from inexpensive beta-aminopropanoic acid in 62% overall yield. Prochiral enolate derivative 1-Li was alkylated in good yield and moderate enantioselectivity in the presence of chiral amines (S)-8, (S,S)-9, (S,S)-10, or (-)-sparteine. The enantioselectivity of the alkylation process is highest in toluene as the solvent and in the presence of lithium bromide as additive. The racemic alkylated derivatives 2 and 3 were readily metallated with LDA to give prochiral enolates 2-Li and 3-Li, that were reprotonated with novel chiral phenolic acids (S)-11, (S,S)-12, (S)-13, and (S,S)-14 in moderate enantioselectivity in the case of 2-Li and good enantioselectivity in the case of 3-Li. The acid (6N HCl) hydrolysis of enantioenriched 2 and 3 proceeded in good yield and without racemization to afford alpha-alkyl-beta-amino acids 4 and 5, respectively. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00578-7

文献信息

• Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids
  作者：Omar Muñoz-Muñiz、Eusebio Juaristi

  DOI：10.1016/s0040-4020(03)00578-7

  日期：2003.6

  Achiral 1-benzoyl-3-methylperhydropyrimidin-4-one (1) was deemed a useful, potential precursor for the enantioselective synthesis of alpha-substituted beta-amino acids. Pyrimidinone 1 was prepared from inexpensive beta-aminopropanoic acid in 62% overall yield. Prochiral enolate derivative 1-Li was alkylated in good yield and moderate enantioselectivity in the presence of chiral amines (S)-8, (S,S)-9, (S,S)-10, or (-)-sparteine. The enantioselectivity of the alkylation process is highest in toluene as the solvent and in the presence of lithium bromide as additive. The racemic alkylated derivatives 2 and 3 were readily metallated with LDA to give prochiral enolates 2-Li and 3-Li, that were reprotonated with novel chiral phenolic acids (S)-11, (S,S)-12, (S)-13, and (S,S)-14 in moderate enantioselectivity in the case of 2-Li and good enantioselectivity in the case of 3-Li. The acid (6N HCl) hydrolysis of enantioenriched 2 and 3 proceeded in good yield and without racemization to afford alpha-alkyl-beta-amino acids 4 and 5, respectively. (C) 2003 Published by Elsevier Science Ltd.
• Munoz-Muniz, Omar; Juaristi, Eusebio, Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3781 - 3785
  作者：Munoz-Muniz, Omar、Juaristi, Eusebio

  DOI：——

  日期：——