diethyl 2,2-difluoro-1-(4-methoxyphenyl)ethenyl phosphate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2,2-difluoro-1-(4-methoxyphenyl)ethenyl phosphate
• 英文别名: [2,2-Difluoro-1-(4-methoxyphenyl)ethenyl] diethyl phosphate
• 化学式: C₁₃H₁₇F₂O₅P
• 分子量: 322.246
• InChiKey: FMIIEAOPDHTTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  diethyl (4-methoxybenzoyl)phosphonate 、 (三氟甲基)三甲基硅烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到diethyl 2,2-difluoro-1-(4-methoxyphenyl)ethenyl phosphate
  参考文献：
  名称：

  Addition of Trifluoromethyltrimethylsilane to Acyl Phosphonates:  Synthesis of TMS-Protected 1-Alkyl-1-trifluoromethyl-1-hydroxyphosphonates and 1-Aryldifluoroethenyl Phosphates

  摘要：

  Addition reactions of nucleophilic CF3TMS to acyl phosphonates were investigated. Various acyl phosphonates reacted readily with CF3TMS in the presence of K2CO3 in DMF at rt to give 1-alkyl-2,2,2-trifluoro-1-trimethylsilyloxyethylphosphonate in 70-90% yields. When benzoyl phosphonates were used as starting material, after addition of CF3, the formed alcoholate undergoes phosphonate-phosphate rearrangement to form the acyl anion, followed by elimination of F- to give 1-aryldifluoroethenyl phosphates in 87-97% yields. As a representative example, vinylphosphate 6a was converted into 2,2-difluoro-1-phenylethanone 7 with 6 N HC1/EtOH/reflux or CAN/NaOH/MeOH/O degrees C in 82-90% yields.

  DOI：

  10.1021/jo070913c

文献信息

• Addition of Trifluoromethyltrimethylsilane to Acyl Phosphonates:  Synthesis of TMS-Protected 1-Alkyl-1-trifluoromethyl-1-hydroxyphosphonates and 1-Aryldifluoroethenyl Phosphates
  作者：Ayhan S. Demir、Serkan Eymur

  DOI：10.1021/jo070913c

  日期：2007.10.1

  Addition reactions of nucleophilic CF3TMS to acyl phosphonates were investigated. Various acyl phosphonates reacted readily with CF3TMS in the presence of K2CO3 in DMF at rt to give 1-alkyl-2,2,2-trifluoro-1-trimethylsilyloxyethylphosphonate in 70-90% yields. When benzoyl phosphonates were used as starting material, after addition of CF3, the formed alcoholate undergoes phosphonate-phosphate rearrangement to form the acyl anion, followed by elimination of F- to give 1-aryldifluoroethenyl phosphates in 87-97% yields. As a representative example, vinylphosphate 6a was converted into 2,2-difluoro-1-phenylethanone 7 with 6 N HC1/EtOH/reflux or CAN/NaOH/MeOH/O degrees C in 82-90% yields.