(Z)-1,2-Dichloro-1,1-difluoro-2-nonen-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1,2-Dichloro-1,1-difluoro-2-nonen-4-one
• 英文别名: (Z)-1,2-dichloro-1,1-difluoronon-2-en-4-one
• 化学式: C₉H₁₂Cl₂F₂O
• 分子量: 245.096
• InChiKey: ABHKWWGFLYRWGT-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-庚酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 tris(triphenylphosphine)ruthenium(II) chloride 4 A molecular sieve 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (Z)-1,2-Dichloro-1,1-difluoro-2-nonen-4-one
  参考文献：
  名称：

  Two-step synthesis of (.gamma.,.gamma.-difluoroallyl)carbonyl compounds via addition of 1,1,2-trichloro-2,2-difluoroethyl radical to silyl enol ethers followed by reductive dechlorination

  摘要：

  Ru(II)- or Cu(I)-induced radical reaction of CF2ClCCl2. radical (2), regioselectively derived from CF2ClCCl3, to trimethylsilyl enol ethers and a ketene silyl acetal yields (beta,beta,gamma-trichloro-gamma,gamma-difluoropropyl)carbonyl compounds 5 as the intermediates. Spontaneous dehydrochlorination affords [beta-chloro-beta-(chlorodifluoromethyl)vinyl]carbonyl compounds 4. Reductive dechlorination of 4 with zinc gave gamma,gamma-difluoroallyl ketones 7a-e and an ester 7f. In some cases, Ni(0)-catalyzed reduction with zinc is superior than the simple hydrodechlorination.

  DOI：

  10.1021/jo00071a027

文献信息

• Two-step synthesis of (.gamma.,.gamma.-difluoroallyl)carbonyl compounds via addition of 1,1,2-trichloro-2,2-difluoroethyl radical to silyl enol ethers followed by reductive dechlorination
  作者：Takashi Okano、Toshihiro Shimizu、Koji Sumida、Shoji Eguchi

  DOI：10.1021/jo00071a027

  日期：1993.9

  Ru(II)- or Cu(I)-induced radical reaction of CF2ClCCl2. radical (2), regioselectively derived from CF2ClCCl3, to trimethylsilyl enol ethers and a ketene silyl acetal yields (beta,beta,gamma-trichloro-gamma,gamma-difluoropropyl)carbonyl compounds 5 as the intermediates. Spontaneous dehydrochlorination affords [beta-chloro-beta-(chlorodifluoromethyl)vinyl]carbonyl compounds 4. Reductive dechlorination of 4 with zinc gave gamma,gamma-difluoroallyl ketones 7a-e and an ester 7f. In some cases, Ni(0)-catalyzed reduction with zinc is superior than the simple hydrodechlorination.