(R)-2-(2-methoxyphenoxy)propanoic acid | 46295-78-7

• 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: (R)-2-(2-methoxyphenoxy)propanoic acid
• 英文别名: (2R)-2-(2-methoxyphenoxy)propanoic acid
• CAS: 46295-78-7
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: OPYAFQUFAKCNPN-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-甲氧基苯氧基)丙酸 、 二-1-萘甲醇 在 (+)-苯并四咪唑 、 三甲基乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到
  参考文献：
  名称：

  A New Method for Production of Chiral 2-Aryloxypropanoic Acids Using Effective Kinetic Resolution of Racemic 2-Aryloxycarboxylic Acids

  摘要：

  We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv(2)O) as an activating agent, bis(alpha-naphthyl)methanol ((alpha-Np)(2)CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.

  DOI：

  10.3987/com-12-s(n)79

文献信息

• A New Method for Production of Chiral 2-Aryloxypropanoic Acids Using Effective Kinetic Resolution of Racemic 2-Aryloxycarboxylic Acids
  作者：Isamu Shiina、Atsushi Tengeiji、Kenya Nakata、Keisuke Ono

  DOI：10.3987/com-12-s(n)79

  日期：——

  We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv(2)O) as an activating agent, bis(alpha-naphthyl)methanol ((alpha-Np)(2)CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.