dimethyl 3,3,3-trifluoro-2-chloroacetyloxypropanephosphonate | 521316-59-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl 3,3,3-trifluoro-2-chloroacetyloxypropanephosphonate
• 英文别名: [3-[Dimethoxy(oxido)phosphaniumyl]-1,1,1-trifluoropropan-2-yl] 2-chloroacetate；[3-[dimethoxy(oxido)phosphaniumyl]-1,1,1-trifluoropropan-2-yl] 2-chloroacetate
• CAS: 521316-59-6
• 化学式: C₇H₁₁ClF₃O₅P
• 分子量: 298.583
• InChiKey: LFTDLHVZACJHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 3,3,3-trifluoro-2-chloroacetyloxypropanephosphonate 在 Candida antarctica lipase B 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 正丁醇 、 苯 为溶剂， 反应 28.0h， 生成 (R)-dimethyl 3,3,3-trifluoro-2-hydroxypropanephosphonate (S)-Mosher's ester
  参考文献：
  名称：

  Enzymatic synthesis of optically active trifluoromethylated 1- and 2-hydroxyalkanephosphonates

  摘要：

  Convenient enzymatic methods have been developed for the preparation of chiral 1- and 2-hydroxyalkanephosphonates bearing a trifluoromethyl moiety with high enantiomeric excess via Candida antarctica lipase B-, Mucor miehei lipase-catalyzed alcoholysis and C. rugosa lipase-catalyzed hydrolysis in organic media. The enantiomeric excess of such trifluoromethylated carbinols was determined using quinine as a chiral solvating agent. The catalytic preference was assigned according to the Kusumi-Ohtani method. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01559-4
• 作为产物：
  描述：

  氯乙酸 、 Dimethyl(3,3,3-trifluoro-2-oxopropyl)phosphonate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 dimethyl 3,3,3-trifluoro-2-chloroacetyloxypropanephosphonate
  参考文献：
  名称：

  Enzymatic synthesis of optically active trifluoromethylated 1- and 2-hydroxyalkanephosphonates

  摘要：

  Convenient enzymatic methods have been developed for the preparation of chiral 1- and 2-hydroxyalkanephosphonates bearing a trifluoromethyl moiety with high enantiomeric excess via Candida antarctica lipase B-, Mucor miehei lipase-catalyzed alcoholysis and C. rugosa lipase-catalyzed hydrolysis in organic media. The enantiomeric excess of such trifluoromethylated carbinols was determined using quinine as a chiral solvating agent. The catalytic preference was assigned according to the Kusumi-Ohtani method. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01559-4