(Z)-2-Fluoro-3-pentafluorophenyl-but-2-enedioic acid diethyl ester | 145343-57-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-Fluoro-3-pentafluorophenyl-but-2-enedioic acid diethyl ester
• 英文别名: diethyl (Z)-2-fluoro-3-(2,3,4,5,6-pentafluorophenyl)but-2-enedioate
• CAS: 145343-57-3
• 化学式: C₁₄H₁₀F₆O₄
• 分子量: 356.221
• InChiKey: CZNOKMNERMHFAF-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  五氟苯基溴化镁 、 2-(Diethoxy-phosphoryl)-2-fluoro-3-oxo-succinic acid diethyl ester 以 四氢呋喃 、 乙醚 为溶剂， 生成 (Z)-2-Fluoro-3-pentafluorophenyl-but-2-enedioic acid diethyl ester 、 (E)-2-Fluoro-3-pentafluorophenyl-but-2-enedioic acid diethyl ester
  参考文献：
  名称：

  An expedient synthesis of α-fluoro-α,β-unsaturated diesters

  摘要：

  Acylation of [(EtO)2P(O)CFCO2Et]-Li+ (2) with alkyloxalyl chlorides followed by subsequent reaction of the acylated phosphonates with Grignard reagents provides the title compounds in moderate to good yields with high E-stereoselectivity.

  DOI：

  10.1016/s0040-4039(00)60990-5

文献信息

• An expedient synthesis of α-fluoro-α,β-unsaturated diesters
  作者：Hou-Jen Tsai、Alagappan Thenappan、Donald J. Burton

  DOI：10.1016/s0040-4039(00)60990-5

  日期：1992.10

  Acylation of [(EtO)2P(O)CFCO2Et]-Li+ (2) with alkyloxalyl chlorides followed by subsequent reaction of the acylated phosphonates with Grignard reagents provides the title compounds in moderate to good yields with high E-stereoselectivity.
• A Novel Intramolecular Horner-Wadsworth-Emmons Reaction: A Simple and General Route to .alpha.-Fluoro-.alpha.,.beta.-unsaturated Diesters
  作者：Hou-Jen Tsai、Alagappan Thenappan、Donald J. Burton

  DOI：10.1021/jo00102a038

  日期：1994.11

  Diethyl (fluorocarbethoxymethyl)phosphonate (1), prepared from triethyl phosphite and ethyl bbromofluoroacetate, reacts with n-butyllithium in THF to give the phosphonate carbanion 2. Addition of the pregenerated carbanion 2 to a THF solution of methyl or ethyl oxalyl chloride at -78 degrees C forms the acylated phosphonate (EtO)(2)P(O)CF(COCO(2)R)CO(2)Et (3). In situ reaction of 3 with Grignard reagents affords alpha-fluoro-alpha,beta-unsaturated diesters R'(CO(2)R)C=CFCO(2)Et in moderate to good yields with high E-stereoselectivity. The reaction is applicable to primary, secondary, and tertiary alkyl, alkenyl, alkynyl, aryl, cyclohexyl, and perfluorinated Grignard reagents. The assignment of E and Z configuration is based on NOE experiment. The E/Z ratio of unsaturated diesters formed in the reaction varies with the metal ion and cosolvent. However, solvents and bases have little influence on the stereoselectivity.