(S)-(+)-2-methoxy-2-(2-naphthyl)propionic acid | 299397-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(+)-2-methoxy-2-(2-naphthyl)propionic acid
• 英文别名: (S)-2-methoxy-2-(2-naphthyl)propanoic acid；(S)-2-Methoxy-2-naphthalen-2-YL-propionic acid；(2S)-2-methoxy-2-naphthalen-2-ylpropanoic acid
• CAS: 299397-14-1
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: PATHKUFURGNLJU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 、 (S)-(+)-2-methoxy-2-(2-naphthyl)propionic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (S)-((S)-2-Methoxy-2-naphthalen-2-yl-propionylamino)-phenyl-acetic acid methyl ester
  参考文献：
  名称：

  Absolute configurations of 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(2-naphthyl)propionic acid as determined by the phenylglycine methyl ester (PGME) method

  摘要：

  The absolute configurations of 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(2-naphthyl)propionic acid were reconfirmed by NMR analyses of phenylglycine methyl ester (PGME) derivatives. Their absolute configurations determined by the PGME method are consistent with those obtained by the H-1 NMR anisotropy method and X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00268-9
• 作为产物：
  描述：

  2-naphthalenylmagnesium bromide 在 sodium hydroxide 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (S)-(+)-2-methoxy-2-(2-naphthyl)propionic acid
  参考文献：
  名称：

  Absolute configuration of 2-methoxy-2-(2-naphthyl)propionic acid as determined by the 1 H NMR anisotropy method

  摘要：

  2-Methoxy-2-(2-naphthyl)propionic acid 1 and 2-hydroxy-2-(2-naphthyl)propionic acid 2 were prepared by the Grignard reaction of 2-naphthylmagnesium bromide with (1R,2S,5R)-(-)-menthyl pyruvate. The absolute configurations of (+)-1 and (+)-2 were determined to be S by the H-1 NMR anisotropy method. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00233-0

文献信息

• Crystal structures and chiral recognition of the diastereomeric salts prepared from 2-methoxy-2-(1-naphthyl)propanoic acid
  作者：Akio Ichikawa、Hiroshi Ono、Takuya Echigo、Yuji Mikata

  DOI：10.1039/c1ce05155e

  日期：——

  to report the structures of crystalline diastereomeric salts 8 and 9 prepared from (R)-2-methoxy-2-(1-naphthyl)propanoic acid [(R)-MαNP acid, (R)-1] and (S)-1 with (R)-1-phenylethylamine [(R)-PEA, (R)-7], respectively. These crystal structures helped elucidate a novel chiral recognition mechanism characteristic of MαNP salts. The less-soluble diastereomeric salt 8 prepared from (R)-1 and (R)-7 formed

  本文是首次报道结晶非对映盐的结构8和9由（- [R）-2-甲氧基-2-（1-萘基）丙酸[（[R）-MαNP酸，（- [R ） - 1 ]和（S）-1与（R）-1-苯基乙胺[（R）-PEA，（R）-7 ]。这些晶体结构有助于阐明MαNP盐的新型手性识别机制。由（R）-1和（R）-7制备的难溶非对映异构体盐8通过甲氧基辅助的盐桥和芳香族CH⋯π相互作用形成铵-羧酸根离子对。由（S）-1和（R）-7制备的更易溶的非对映异构体盐9通过甲氧基辅助的盐桥形成离子对，其中1-萘基和苯基不重叠。相反，盐9借助于盐桥，CH 3 O氢键和π1π相互作用形成了紧密的离子对。这些晶体结构表明，从包含羧基和甲氧基的MαNP平面开始的分子长度对于非对映体盐的结晶至关重要。研究了两种盐在弱相互作用（即盐桥，NH 3 O和CH 3 O氢键以及芳族CH 3π，CH 3π和π3π相互作用）中的晶体堆积。最后，非对映异构酰胺1
• Absolute configuration of 2-methoxy-2-(2-naphthyl)propionic acid as determined by the 1 H NMR anisotropy method
  作者：Akio Ichikawa、Syuntaro Hiradate、Akinori Sugio、Shunsuke Kuwahara、Masataka Watanabe、Nobuyuki Harada

  DOI：10.1016/s0957-4166(00)00233-0

  日期：2000.7

  2-Methoxy-2-(2-naphthyl)propionic acid 1 and 2-hydroxy-2-(2-naphthyl)propionic acid 2 were prepared by the Grignard reaction of 2-naphthylmagnesium bromide with (1R,2S,5R)-(-)-menthyl pyruvate. The absolute configurations of (+)-1 and (+)-2 were determined to be S by the H-1 NMR anisotropy method. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Absolute configurations of 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(2-naphthyl)propionic acid as determined by the phenylglycine methyl ester (PGME) method
  作者：Akio Ichikawa、Hiroshi Ono、Syuntaro Hiradate、Masataka Watanabe、Nobuyuki Harada

  DOI：10.1016/s0957-4166(02)00268-9

  日期：2002.6

  The absolute configurations of 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(2-naphthyl)propionic acid were reconfirmed by NMR analyses of phenylglycine methyl ester (PGME) derivatives. Their absolute configurations determined by the PGME method are consistent with those obtained by the H-1 NMR anisotropy method and X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.