N-[4,4-difluoro-2,2-dimethyl-1-(2-phenylethyl)but-3-en-1-ylidene]-4-methylbenzenesulfonamide | 1629870-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4,4-difluoro-2,2-dimethyl-1-(2-phenylethyl)but-3-en-1-ylidene]-4-methylbenzenesulfonamide
• 英文别名: N-(6,6-difluoro-4,4-dimethyl-1-phenylhex-5-en-3-ylidene)-4-methylbenzenesulfonamide
• CAS: 1629870-87-6
• 化学式: C₂₁H₂₃F₂NO₂S
• 分子量: 391.482
• InChiKey: SKTUFZYQJRQRPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4,4-difluoro-2,2-dimethyl-1-(2-phenylethyl)but-3-en-1-ylidene]-4-methylbenzenesulfonamide 在 potassium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 以61%的产率得到N-[(1Z)-4,4-difluoro-2,2-dimethyl-1-(2-phenylethylidene)but-3-en-1-yl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles

  摘要：

  Metal enolates and enamides bearing difluoroallylic moieties underwent nucleophilic 5-endo-trig cyclization, a process considered to be disfavored according to Baldwin's rules. Whereas no C-cyclization was observed in these reactions, O- and N-cyclization proceeded exclusively to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans and -2,3-dihydropyrroles, respectively.

  DOI：

  10.1055/s-0033-1340857
• 作为产物：
  描述：

  2,2-dimethyl-3-oxo-5-phenylpentanal 在 三乙胺 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 40.33h， 生成 N-[4,4-difluoro-2,2-dimethyl-1-(2-phenylethyl)but-3-en-1-ylidene]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles

  摘要：

  Metal enolates and enamides bearing difluoroallylic moieties underwent nucleophilic 5-endo-trig cyclization, a process considered to be disfavored according to Baldwin's rules. Whereas no C-cyclization was observed in these reactions, O- and N-cyclization proceeded exclusively to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans and -2,3-dihydropyrroles, respectively.

  DOI：

  10.1055/s-0033-1340857

文献信息

• Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Metal Enolates and Enamides: Facile Synthesis of Ring-Fluorinated Dihydroheteroles
  作者：Junji Ichikawa、Takeshi Fujita、Masahiro Ikeda、Masahiro Hattori、Kotaro Sakoda

  DOI：10.1055/s-0033-1340857

  日期：——

  Metal enolates and enamides bearing difluoroallylic moieties underwent nucleophilic 5-endo-trig cyclization, a process considered to be disfavored according to Baldwin's rules. Whereas no C-cyclization was observed in these reactions, O- and N-cyclization proceeded exclusively to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans and -2,3-dihydropyrroles, respectively.