O,O-diethyl-O-(1-trifluoromethyl-2,2,2-trifluoroethyl)phosphate | 19784-22-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: O,O-diethyl-O-(1-trifluoromethyl-2,2,2-trifluoroethyl)phosphate
• 英文别名: O,O-diethyl O-(1,1,1,3,3,3-hexafluoropropan-2-yl) phosphate；phosphoric acid diethyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester；Diethyl-(β,β,β,β,β,β-hexafluor-isopropyl)-phosphat；1,1,1,3,3,3-Hexafluoroisopropyl-diethylphosphonat；Diethyl 1,1,1,3,3,3-hexafluoropropan-2-yl phosphate
• CAS: 19784-22-6
• 化学式: C₇H₁₁F₆O₄P
• 分子量: 304.126
• InChiKey: YEMNWQQLKIIPRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Diethyl-2-hydroxy-1,1,1,3,3,3-hexafluoroisopropyl-phosphonat 在 三乙胺 作用下， 反应 0.5h， 生成 O,O-diethyl-O-(1-trifluoromethyl-2,2,2-trifluoroethyl)phosphate
  参考文献：
  名称：

  Synthesis of organophosphates with fluorine-containing leaving groups as serine esterase inhibitors with potential for Alzheimer disease therapeutics

  摘要：

  Acetylcholinesterase and butyrylcholinesterase inhibitors are potential cognition enhancers in Alzheimer disease. O,O-Dialkylphosphate inhibitors with 1-substituted 2,2,2-trifluoroethoxy leaving groups were synthesized by phosphonate-phosphate rearrangement. Substituents in the 1-position of the leaving group along with the O-alkyl groups modulated potency and selectivity against acetylcholinesterase, butyrylcholinesterase, and carboxylesterase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.065

文献信息

• Synthesis of O-phosphorylated 1-substituted 2,2,2-trifluoroethanols, serine hydrolase inhibitors
  作者：A. Yu. Aksinenko、V. B. Sokolov、T. V. Goreva、G. F. Makhaeva

  DOI：10.1007/s11172-010-0050-2

  日期：2010.1

  Reactivity of trifluoromethyl carbonyl compounds in a two-step reaction with dialkyl phos-phites (the Abramov reaction and phosphonate—phosphate rearrangement) has been studied and the scope of this reaction for the preparation of O-phosphorylated 1-substituted 2,2,2-trifluoro-ethanols, serine hydrolase inhibitors, has been determined.

  研究了三氟甲基羰基化合物在与亚磷酸二烷基酯（阿布拉莫夫反应和膦酸酯-磷酸重排）的两步反应中的反应性，以及该反应制备 O-磷酸化 1-取代 2,2,2 的范围-三氟乙醇，丝氨酸水解酶抑制剂，已被确定。
• Ivin,S.Z. et al., Journal of general chemistry of the USSR, 1967, vol. 37, # 11, p. 2388 - 2390
  作者：Ivin,S.Z. et al.

  DOI：——

  日期：——
• The synthesis and reactions of dialkyl fluoroalkyl phosphates
  作者：Christopher M Timperley、Ian J Morton、Matthew J Waters、Jason L Yarwood

  DOI：10.1016/s0022-1139(99)00065-2

  日期：1999.6

  Dimethyl and diethyl fluoroalkyl phosphates were prepared from (1) a dialkyl phosphite with a fluoroalcohol, triethylamine and carbon tetrachloride, (2) a dialkyl chlorophosphate with a fluoroalcohol and triethylamine, and (3) a dialkyl chlorophosphate with the sodium salt of a fluoroalcohol. Dimethyl and diethyl (2,2,2-trifluoroethyl) phosphates reacted with bromotrimethylsilane (TMSBr) in chloroform to give two products with loss of alkyl bromide. The major product was an alkyl (trifluoroethyl) trimethylsilyl phosphate, RO(TMSO)P(O)OCH2CF3 and the minor product was a bis(trimethylsilyl) trifluoroethyl phosphate, (TMSO)(2)P(O)OCH2CF3. The mechanism presumably involves initial attack of an alkoxy oxygen atom on the silicon atom of bromotrimethylsilane. Diethyl (2,2,2-trifluoroethyl) phosphate is resistant to chlorination. It did not react with oxalyl or thionyl chloride in chloroform under prolonged reflux. Unlike triethyl phosphate, it did not react with phosphorus oxychloride in chloroform under reflux. (C) 1999 Elsevier Science S.A. All rights reserved.
• KRYUKOV L. N.; KRYUKOVA L. YU.; ISAEV V. L.; STERLIN R. N.; KNUNYANTS I. +, DOKL. AN CCCP, 1979, 247, HO 1, 115-117
  作者：KRYUKOV L. N.、 KRYUKOVA L. YU.、 ISAEV V. L.、 STERLIN R. N.、 KNUNYANTS I. +

  DOI：——

  日期：——
• Synthesis of organophosphates with fluorine-containing leaving groups as serine esterase inhibitors with potential for Alzheimer disease therapeutics
  作者：Galina F. Makhaeva、Alexey Y. Aksinenko、Vladimir B. Sokolov、Olga G. Serebryakova、Rudy J. Richardson

  DOI：10.1016/j.bmcl.2009.08.065

  日期：2009.10

  Acetylcholinesterase and butyrylcholinesterase inhibitors are potential cognition enhancers in Alzheimer disease. O,O-Dialkylphosphate inhibitors with 1-substituted 2,2,2-trifluoroethoxy leaving groups were synthesized by phosphonate-phosphate rearrangement. Substituents in the 1-position of the leaving group along with the O-alkyl groups modulated potency and selectivity against acetylcholinesterase, butyrylcholinesterase, and carboxylesterase. (C) 2009 Elsevier Ltd. All rights reserved.