diethyl 1,2-dihydroxy-3,3,3-trifluoropropanephosphonate | 153650-93-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 1,2-dihydroxy-3,3,3-trifluoropropanephosphonate
• 英文别名: diethyl 1,2-dihydroxy-3,3,3-trifluoropropylphosphonate
• CAS: 153650-93-2
• 化学式: C₇H₁₄F₃O₅P
• 分子量: 266.154
• InChiKey: WUTMZFUUGUTNRK-UHFFFAOYSA-N

物化性质

• 沸点：
  379.8±42.0 °C(predicted)
• 密度：
  1.378±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 diethyl 1,2-dihydroxy-3,3,3-trifluoropropanephosphonate 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， 以90%的产率得到diethyl 1,2-di(β-chloroacetyloxy)-3,3,3-trifluoropropanephosphonate
  参考文献：
  名称：

  A facial chemoenzymatic method for the preparation of chiral 1,2-dihydroxy-3,3,3,-trifluoropropanephosphonates

  摘要：

  A convenient and effective method for the preparation of chiral trifluoromethylated 1,2-dihydroxypropanephosphonates based on a chemoenzymatic approach was described. Ethyl trifluoromethylacetate was reacted with anion of methylphosphonate to give 2-oxo-3,3,3-tri fluoropropanephosphonate and its hydrates, 2,2-dihydroxy-3,3,3-trifluoropropanephosphonates, which are reduced with sodium boronhydride affording 2-hydroxy-3,3,3-trifluoropropanephosphonates. The product thus obtained was then transferred to corresponding 1,2-vinyl-3,3,3-trifluoropropanephosphonate and followed by 1,2-dihydroxylation via potassium permanganate treatment. Enzymatic kinetic resolution of the resultant racemate by CALB or IM provided optically active 1,2-dihydroxy-3,3,3-trifluoropropanephosphonate with satisfactory chemical and enantiomeric yield. (C) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.08.017
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 在 吡啶 、 四氧化锇 、 正丁基锂 作用下， 反应 25.0h， 生成 diethyl 1,2-dihydroxy-3,3,3-trifluoropropanephosphonate
  参考文献：
  名称：

  A convenient synthesis of perfluoroalkylated hydroxy- and dihydroxy-phosphonates

  摘要：

  Perfluoroalkylated 1-hydroxyphosphonates may be easily synthesized in good yield by the reaction of the corresponding perfluoroalkyl aldehydes with dimethyl phosphite. Perfluoroalkylcarboxylic esters react with the phosphonate anion to give (perfluoroacyl)methylphosphonates, their tautomeric isomers (2-perfluoroalkyl-2-hydroxy)vinylphosphonates and their hydrates (2-perfluoroalkyl-2,2-dihydroxy)ethylphosphonates, which are reduced with sodium borohydride affording perfluoroalkylated 2-hydroxyphosphonates in 61-68% yield. Perfluoroalkylated dihydroxyphosphonates may be obtained by the reaction of the bisphosphonate anion with perfluoroalkyl aldehydes followed by oxidation with osmium tetraoxide in 54-68% yield.

  DOI：

  10.1016/s0022-1139(00)80472-8