2-(Diisopropoxy-phosphoryl)-2-fluoro-3-oxo-succinic acid diethyl ester | 292074-10-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(Diisopropoxy-phosphoryl)-2-fluoro-3-oxo-succinic acid diethyl ester
• CAS: 292074-10-3
• 化学式: C₁₄H₂₄FO₈P
• 分子量: 370.312
• InChiKey: MVJWFKHNMZMVFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 2-(Diisopropoxy-phosphoryl)-2-fluoro-3-oxo-succinic acid diethyl ester 以 四氢呋喃 、 乙醚 为溶剂， 生成 diethyl-2-fluoro-3-methyl fumarate
  参考文献：
  名称：

  STEREOSELECTIVE SYNTHESIS OF MONOFLUORO-OLEFINS FROM DIISOPROPYL (CARBOETHOXYFLUORO-METHYL)PHOSPHONATE

  摘要：

  Treatment of ethyl oxalyl chloride or methyl oxalyl chloride with lithium diisopropyl(carboethoxyfluoromethyl)phosphonate [(i-PrO)(2)P(O)CFCO2Et]Li--(+) 2 followed by in situ nucleophilic addition with methylmagnesium iodide or vinyl magnesium bromide affords with exclusive E-stereoselectivity formation of diethyl-2-fluoro-3-methyl fumarate (CH3)(CO2Et)C=CFCO2Et 4 or 75% of the E-isomer of alpha-fluoro-beta-vinyl-alpha,beta-unsaturated diester (E,Z)-(CH2=CH)(CO2C2H5)C=CFCO2Et 5, respectively. However, direct reaction of ethyl pyruvate with 2 gives the fluoro-olefin (CH3)(CO2Et)C=CFCO2Et 4 with 79% E-stereoselectivity. The E/Z ratio of (CH2=CH)(CO2Et)C=CFCO2Et 5 depends on the HMPT or DMPU cosolvents present in the reaction mixture.

  DOI：

  10.1080/10426500008042107
• 作为产物：
  描述：

  diisopropyl(fluorocarbethoxymethyl)phosphonate 、 草酰氯单乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 2-(Diisopropoxy-phosphoryl)-2-fluoro-3-oxo-succinic acid diethyl ester
  参考文献：
  名称：

  STEREOSELECTIVE SYNTHESIS OF MONOFLUORO-OLEFINS FROM DIISOPROPYL (CARBOETHOXYFLUORO-METHYL)PHOSPHONATE

  摘要：

  Treatment of ethyl oxalyl chloride or methyl oxalyl chloride with lithium diisopropyl(carboethoxyfluoromethyl)phosphonate [(i-PrO)(2)P(O)CFCO2Et]Li--(+) 2 followed by in situ nucleophilic addition with methylmagnesium iodide or vinyl magnesium bromide affords with exclusive E-stereoselectivity formation of diethyl-2-fluoro-3-methyl fumarate (CH3)(CO2Et)C=CFCO2Et 4 or 75% of the E-isomer of alpha-fluoro-beta-vinyl-alpha,beta-unsaturated diester (E,Z)-(CH2=CH)(CO2C2H5)C=CFCO2Et 5, respectively. However, direct reaction of ethyl pyruvate with 2 gives the fluoro-olefin (CH3)(CO2Et)C=CFCO2Et 4 with 79% E-stereoselectivity. The E/Z ratio of (CH2=CH)(CO2Et)C=CFCO2Et 5 depends on the HMPT or DMPU cosolvents present in the reaction mixture.

  DOI：

  10.1080/10426500008042107