2,2-difluoro-pentan-3-one | 683-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-pentan-3-one
• 英文别名: 2.2-Difluopr-pentanon-3；2,2-difluoropentan-3-one
• CAS: 683-95-4
• 化学式: C₅H₈F₂O
• 分子量: 122.115
• InChiKey: UJMDRELRMSOIMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2,3-戊二酮 在 乙醇 、 [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 24.0h， 生成 2,2-difluoro-pentan-3-one 、 3,3-difluoro-pentan-2-one 、 2,2,3,3-四氟戊烷
  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