(S)-ethyl 2-((R)-1-phenylethylamino)-2-(2-hydroxynaphthalen-1-yl)acetate | 1309650-26-7

• 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: (S)-ethyl 2-((R)-1-phenylethylamino)-2-(2-hydroxynaphthalen-1-yl)acetate
• 英文别名: ethyl (2S)-2-(2-hydroxynaphthalen-1-yl)-2-[[(1R)-1-phenylethyl]amino]acetate
• CAS: 1309650-26-7
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: ASQAKIASDMFBMV-VFNWGFHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 在 sodium sulfate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (R)-ethyl 2-((R)-1-phenylethylamino)-2-(2-hydroxynaphthalen-1-yl)acetate 、 (S)-ethyl 2-((R)-1-phenylethylamino)-2-(2-hydroxynaphthalen-1-yl)acetate
  参考文献：
  名称：

  Enantiopure α-imino glyoxylate: a versatile substrate for the spontaneous asymmetric synthesis of unnatural hydroxyaryl glycinates

  摘要：

  A novel synthesis of useful enantiomerically pure arylglycinates via spontaneous reaction between phenol or naphthol derivatives and enantiopure alpha-imino glyoxylate in the absence of an acid catalyst is reported. A library of enantiopure substituted phenol or naphthol glycinates was obtained in good yields and high diastereoselectivities. Diastereoisomerically pure aryl glycinates were obtained by direct flash chromatography separation of the crude reaction mixture. The free OH moiety of the phenols or naphthols contributed to the activation of the imino group to form an intermolecular hydrogen bond and promoted the reaction in the absence of an acid catalyst, as shown in the transition state reported. The diastereoselectivity is due to thermodynamic control in the addition step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.008

文献信息

• Enantiopure α-imino glyoxylate: a versatile substrate for the spontaneous asymmetric synthesis of unnatural hydroxyaryl glycinates
  作者：Cristina Cimarelli、Davide Fratoni、Andrea Mazzanti、Gianni Palmieri

  DOI：10.1016/j.tetasy.2011.03.008

  日期：2011.3

  A novel synthesis of useful enantiomerically pure arylglycinates via spontaneous reaction between phenol or naphthol derivatives and enantiopure alpha-imino glyoxylate in the absence of an acid catalyst is reported. A library of enantiopure substituted phenol or naphthol glycinates was obtained in good yields and high diastereoselectivities. Diastereoisomerically pure aryl glycinates were obtained by direct flash chromatography separation of the crude reaction mixture. The free OH moiety of the phenols or naphthols contributed to the activation of the imino group to form an intermolecular hydrogen bond and promoted the reaction in the absence of an acid catalyst, as shown in the transition state reported. The diastereoselectivity is due to thermodynamic control in the addition step. (C) 2011 Elsevier Ltd. All rights reserved.