2-{[(2-hydroxynaphthalen-1-yl)phenylmethyl]amino}-3-methylbutyric acid methyl ester | 1610924-11-2

• 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-{[(2-hydroxynaphthalen-1-yl)phenylmethyl]amino}-3-methylbutyric acid methyl ester
• 英文别名: (S,S)-2-((2-hydroxynaphth-1-yl)benzylamino)-3-methylbutanoic acid methyl ester
• CAS: 1610924-11-2
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: ANWRQCZNDSOLSX-VXKWHMMOSA-N

物化性质

• 熔点：
  156-158 °C(Solvent: Ethanol)
• 沸点：
  513.1±45.0 °C(predicted)
• 密度：
  1.156±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  L-缬氨酸甲酯 、 苯甲醛 、 2-萘酚 反应 72.0h， 以26%的产率得到2-{[(2-hydroxynaphthalen-1-yl)phenylmethyl]amino}-3-methylbutyric acid methyl ester
  参考文献：
  名称：

  光学活性aminonaphthols作为NMR的溶剂化剂为扁桃酸的手性识别应用

  摘要：

  一系列光学活性氨基萘酚衍生物的制备和筛选作为手性溶解剂以鉴别与c α由外消旋扁桃酸为h 1点H NMR分析。努力是为了建立在该非共价相互作用氨基萘酚衍生物的结构和选择性的相关性。通过指示系统可能用于确定未知对映体纯度的扁桃酸样品的ee，建立了实验对映体和计算对映体纯度之间的线性关系。

  DOI：

  10.1016/j.tetasy.2014.04.003

文献信息

• Stereoselection in the Betti reaction of valine methyl esters
  作者：Maria Annunziata M. Capozzi、Cosimo Cardellicchio

  DOI：10.1016/j.tetasy.2017.10.026

  日期：2017.12

  The multi-component Betti reaction of 2-naphthol, benzaldehyde and (S)-amines, that usually provides highly valuable aminobenzylnaphthol bearing two stereogenic centers, yielded a completely racemic product, when (S)-valine methyl ester was employed as the amine in the usual reaction protocol. The cause of this drawback, that appears to be overlooked in the literature, was investigated. As a result, new reaction conditions were set up, that were able to yield the expected useful product, having two fully resolved stereogenic centers. Furthermore, when the effect of substituents on the phenyl ring was preliminarily studied, we found that 4-fluoro- and 4-chlorobenzaldeyde gave stereoisomerically pure compounds also in the original reaction protocol. (C) 2017 Elsevier Ltd. All rights reserved.