2-amino-N'-(α-phenylethyl)acetamide | 137348-67-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-amino-N'-(α-phenylethyl)acetamide
• 英文别名: 2-amino-N-[(1S)-1-phenylethyl]acetamide
• CAS: 137348-67-5
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: ISKASNLUPTVDNL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-N'-(α-phenylethyl)acetamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S,S)-1-benzoyl-2-tert-butyl-3-(α-phenylethyl)-1,3-imidazolidin-4-one
  参考文献：
  名称：

  “Alternative method for the resolution of 1-benzoyl-2-tert-butyl-3-methyl-1,3-imidazolidin-4-one”

  摘要：

  The title heterocycles, which are useful chiral precursors for the asymmetric synthesis of alpha-amino acids, can be prepared in enantiomerically pure form via the separation of diastereomeric derivatives incorporating (S)-alpha-methyl-benzylamine.

  DOI：

  10.1016/s0957-4166(00)80465-6
• 作为产物：
  描述：

  2--N''-<(S)-α-methylbenzyl>acetamide 在 palladium on activated charcoal 氢气 作用下， 反应 1.5h， 以100%的产率得到2-amino-N'-(α-phenylethyl)acetamide
  参考文献：
  名称：

  “Alternative method for the resolution of 1-benzoyl-2-tert-butyl-3-methyl-1,3-imidazolidin-4-one”

  摘要：

  The title heterocycles, which are useful chiral precursors for the asymmetric synthesis of alpha-amino acids, can be prepared in enantiomerically pure form via the separation of diastereomeric derivatives incorporating (S)-alpha-methyl-benzylamine.

  DOI：

  10.1016/s0957-4166(00)80465-6

文献信息

• “Alternative method for the resolution of 1-benzoyl-2-tert-butyl-3-methyl-1,3-imidazolidin-4-one”
  作者：Eusebio Juaristi、Benito Rizo、Vicente Natal、Jaime Escalante、Ignacio Regla

  DOI：10.1016/s0957-4166(00)80465-6

  日期：1991.1

  The title heterocycles, which are useful chiral precursors for the asymmetric synthesis of alpha-amino acids, can be prepared in enantiomerically pure form via the separation of diastereomeric derivatives incorporating (S)-alpha-methyl-benzylamine.
• Highly Diastereoselective Alkylation of 1-Benzoyl-2-alkyl-3-(1'-methylbenzyl)imidazolidin-4-ones
  作者：Eusebio Juaristi、Jose Luis Anzorena、Alois Boog、Domingo Madrigal、Dieter Seebach、Efren V. Garcia-Baez、Oscar Garcia-Barradas、Barbara Gordillo、A. Kramer

  DOI：10.1021/jo00125a029

  日期：1995.10

  The synthetic utility of 2-alkyl-substituted 1,3-imidazolidinones for the enantioselective preparation of a-amino acids is now well documented in the literature. Incorporation of a N(3)-phenethyl group in these heterocycles leads to substantial enhancements in the diastereoselectivity of alkylation of the corresponding lithium enolates, so that stereoselectivities in the order of 19:1 to 49:1 are observed for 2-isopropyl and 2-tert-butyl derivatives, respectively. X-ray crystallographic analysis on five N(3)-phenethyl-substituted imidazolidinones provided evidence that the long-distance effect of that chiral moiety is the result of conformational changes provoked by steric interactions between the 2-alkyl and the N(3)-phenethyl groups. No additivity of the stereodirecting effects by the stereogenic centers at C(2) and C(1') was noticed, Thus, as it could have been anticipated from basic principles, intramolecular combinations of stereogenic centers do not necessarily lead to ''matched'' and ''mismatched'' joint stereoinducing effects.