(3E)-3,4-difluoro-3-penten-2-one | 108642-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E)-3,4-difluoro-3-penten-2-one
• 英文别名: (E)-3,4-difluoro-3-penten-2-one；3-Penten-2-one, 3,4-difluoro-, (3E)-(9CI)；(E)-3,4-difluoropent-3-en-2-one
• CAS: 108642-84-8
• 化学式: C₅H₆F₂O
• 分子量: 120.099
• InChiKey: HSVZGXGFJZETGV-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰丙酮 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以39%的产率得到(3E)-3,4-difluoro-3-penten-2-one
  参考文献：
  名称：

  Nucleophilic Di- and Tetrafluorination of Dicarbonyl Compounds

  摘要：

  Reactions of various diketo compounds with Deoxofluor [(CH3OCH2CH2)(2)NSF3] have been investigated. When reacted with Deoxofluor, a-diketones, R1COCOR2 (R-1 = R-2 = Ph; R-1 = R-2 = 4-Me-C6H4; R-1 = Ph, R-2 = Me; R-1 = Me, R-2 = Et) (1a-d) formed difluoro derivatives (2a-d) in the presence of a catalytic amount of HF and/or tetrafluoro (3a-d) products depending on the reaction conditions and stoichiometry used. Reactions of beta -diketones, R3COCH2COR4 (R-3 = R-4 = Ph; R-3 = R-4 = Me; R-3 = Me, R-4 = Ph) (4e-g), with Deoxofluor in the presence of a catalytic amount of HF led to the formation of difluoroalkenones as a mixture of E (5e-g) and Z (6e-g) isomers in good yield. Reaction of other diones, R5CO-X-COR6 (R-5 = R-6 = Ph, X =-CH=CH-; R-5 = R-6 = Me, X = -C6H4C6H4-; R-5 = R-6 = Ph, X = -CH2CH2CH2-; R-5 = R-6 = Me, X = -CH2CH2-) (7h-k) with Deoxofluor produced mainly difluoro products (8h-k) with low yields of tertrafluoro derivatives (9h-k). Acyclic alpha -keto amides react poorly to give the corresponding difluoro derivatives, whereas cyclic (alpha -keto amides (101-p) react smoothly under very mild conditions to produce the corresponding difluoro products (111-p) in > 88% isolated yield.

  DOI：

  10.1021/jo0157674

文献信息

• The preparation of vicinal difluoroolefinic carbonyl compounds and their application to the synthesis of difluororetinal analogs
  作者：A.E Asato、R.S.H Liu

  DOI：10.1016/s0040-4039(00)84789-9

  日期：1986.1

  The preparation of a novel vicinal difluorinated retinal analog is described. The key difluoroolefinic intermediate in the synthesis was prepared by the reaction of DAST with ethyl acetoacetate.

  描述了新颖的邻位二氟化视网膜类似物的制备。合成中的关键二氟烯烃中间体是通过DAST与乙酰乙酸乙酯反应制得的。