diethyl 3,3,3-trifluoropropenylphosphonate | 115162-56-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 3,3,3-trifluoropropenylphosphonate
• 英文别名: (E)-(3,3,3-trifluoropropenyl)phosphonic acid diethyl ester；diethyl (E)-(3,3,3-trifluoroprop-1-en-1-yl)phosphonate；(E)-1-diethoxyphosphoryl-3,3,3-trifluoroprop-1-ene
• CAS: 115162-56-6
• 化学式: C₇H₁₂F₃O₃P
• 分子量: 232.139
• InChiKey: YHWLDJBMOFBQTR-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 3,3,3-trifluoropropenylphosphonate 在 potassium permanganate 作用下， 反应 1.0h， 以48%的产率得到diethyl 1,2-dihydroxy-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：

  diethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate 在 sodium tetrahydroborate 、 水 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 diethyl 3,3,3-trifluoropropenylphosphonate
  参考文献：
  名称：

  The stereospecific synthesis of (Z)- and (E)-diethyl (3,3,3-trifluoro-1-propenyl)phosphonate

  摘要：

  DOI：

  10.1021/jo00251a044

文献信息

• Synthesis of 4-(trifluoromethyl)pyrrolidines Containing Sulfonyl, Iminosulfonyl, Sulfamide, or Phosphonyl Substituent
  作者：Yuriy N. Markitanov、Vadim M. Timoshenko、Yuriy G. Shermolovich、Vladimir L. Mykhalchuk、Irina A. Grafova、Andrei V. Grafov

  DOI：10.1007/s10593-016-1916-5

  日期：2016.7

  New 4-(trifluoromethyl)pyrrolidines containing sulfonyl, iminosulfonyl, sulfamide, or phosphonyl group at position 3 were synthesized by 1,3-dipolar cycloaddition reactions of 3,3,3-trifluoropropene derivatives to azomethine ylide generated in situ from N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine.

  通过3,3,3-三氟丙烯衍生物与N-苄基原位生成的偶氮甲碱内酯的1,3-偶极环加成反应合成了3位上含有磺酰基，亚氨基磺酰基，磺酰胺或膦酰基的新4-（三氟甲基）吡咯烷N-（甲氧基甲基）-N -[（三甲基甲硅烷基）甲基]胺。
• 3-Functional substituted 4-trifluoromethyl tetrahydrothiophenes via [3 + 2]-cycloaddition reactions
  作者：Yuriy M. Markitanov、Vadim M. Timoshenko、Tymofii V. Rudenko、Eduard B. Rusanov、Yuriy G. Shermolovich

  DOI：10.1080/17415993.2019.1633326

  日期：2019.11.2

  New 4-(trifluoromethyl)tetrahydrothiophenes containing an ester, sulfone, sulfoximine, sulfonamide, or phosphonate moiety at position 3 were synthesized by 1,3-dipolar [3 + 2]-cycloaddition reactions of 3,3,3-trifluoropropene derivatives and thiocarbonyl ylide generated in situ from chloromethyl trimethylsilylmethyl sulfide. GRAPHICAL ABSTRACT

  通过 3,3,3-三氟丙烯衍生物和硫代羰基的 1,3-偶极 [3 + 2]-环加成反应合成了在 3 位含有酯、砜、亚砜亚胺、磺酰胺或膦酸酯部分的新型 4-（三氟甲基）四氢噻吩由氯甲基三甲基甲硅烷基甲基硫化物原位生成的叶立德。图形概要
• A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction
  作者：Tsutomu Konno、Tomoo Tanaka、Tomotsugu Miyabe、Atsunori Morigaki、Takashi Ishihara

  DOI：10.1016/j.tetlet.2008.01.122

  日期：2008.3

  Treatment of fluoroalkylated electron-deficient olefins with various boronic acids in the presence of a catalytic amount of Rh(l) coordinated with (S)-BINAP in toluene/H2O at the reflux temperature for 3 h gave the corresponding conjugate addition products with high enantioselectivity in high yields. (C) 2008 Elsevier Ltd. All rights reserved.