diethyl (R)-(2-hydroxy-2-(naphthalen-2-yl)ethyl)phosphonate | 450407-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl (R)-(2-hydroxy-2-(naphthalen-2-yl)ethyl)phosphonate
• 英文别名: (1R)-2-[diethoxy(oxido)phosphaniumyl]-1-naphthalen-2-ylethanol
• CAS: 450407-01-9
• 化学式: C₁₆H₂₁O₄P
• 分子量: 308.314
• InChiKey: GQKXYXMCYIZXIA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl (2-hydroxy-2-(naphthalen-2-yl)ethyl)phosphonate 在 (((CH₃)2N)(CCHCHN)(C₅H₃))Fe(C₅(C₆H₅)5) 、 乙酸酐 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 24.0h， 以32%的产率得到diethyl (R)-(2-hydroxy-2-(naphthalen-2-yl)ethyl)phosphonate
  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