dimethyl (R)-(2-hydroxy-2-(4-nitrophenyl)ethyl)phosphonate | 1239972-47-4

• 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: dimethyl (R)-(2-hydroxy-2-(4-nitrophenyl)ethyl)phosphonate
• 英文别名: (1R)-2-dimethoxyphosphoryl-1-(4-nitrophenyl)ethanol
• CAS: 1239972-47-4
• 化学式: C₁₀H₁₄NO₆P
• 分子量: 275.198
• InChiKey: CBWHLOBFEHFXBK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酸酐 、 二甲基(RS)-2-羟基-2-(4-硝基苯基)乙基膦酸酯 在 (((CH₃)2N)(CCHCHN)(C₅H₃))Fe(C₅(C₆H₅)5) 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 4.0h， 以23%的产率得到
  参考文献：
  名称：

  Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst

  摘要：

  Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.102

文献信息

• Nonenzymatic kinetic resolution of racemic β-hydroxyalkanephosphonates with a chiral copper catalyst
  作者：Atsushi Moriyama、Shintaro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2010.04.059

  日期：2010.4

  Kinetic resolution of beta-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21 (C) 2010 Elsevier Ltd. All rights reserved.
• Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst
  作者：Laura Mesas-Sánchez、Alba E. Díaz-Álvarez、Petr Koukal、Peter Dinér

  DOI：10.1016/j.tet.2014.03.102

  日期：2014.6

  Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee). (C) 2014 Elsevier Ltd. All rights reserved.