1-[1-(2,2-difluorovinyl)cyclohexyl]-3,3-dimethylbutan-1-one | 1426575-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[1-(2,2-difluorovinyl)cyclohexyl]-3,3-dimethylbutan-1-one
• 英文别名: 1-[1-(2,2-Difluoroethenyl)cyclohexyl]-3,3-dimethylbutan-1-one；1-[1-(2,2-difluoroethenyl)cyclohexyl]-3,3-dimethylbutan-1-one
• CAS: 1426575-57-6
• 化学式: C₁₄H₂₂F₂O
• 分子量: 244.325
• InChiKey: KWPNNSVUZXXSGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[1-(2,2-difluorovinyl)cyclohexyl]-3,3-dimethylbutan-1-one 在 potassium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 以94%的产率得到(Z)-1-(2,2-dimethylpropylidene)-3-fluoro-2-oxaspiro[4.5]dec-3-ene
  参考文献：
  名称：

  Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Ketone Enolates: Synthesis of 5-Fluorinated 2-Alkylidene-2,3-dihydrofurans

  摘要：

  3,3-Difluoroallylic ketones readily undergo nucleophilic 5-endo-trig cyclization through their metal enolates to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans. O-Cyclization exclusively occurred via intramolecular substitution of the vinylic fluorines.

  DOI：

  10.1055/s-0032-1317709
• 作为产物：
  描述：

  3,3-二甲基丁酰氯 在 三(二甲胺基)膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.25h， 生成 1-[1-(2,2-difluorovinyl)cyclohexyl]-3,3-dimethylbutan-1-one
  参考文献：
  名称：

  Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Ketone Enolates: Synthesis of 5-Fluorinated 2-Alkylidene-2,3-dihydrofurans

  摘要：

  3,3-Difluoroallylic ketones readily undergo nucleophilic 5-endo-trig cyclization through their metal enolates to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans. O-Cyclization exclusively occurred via intramolecular substitution of the vinylic fluorines.

  DOI：

  10.1055/s-0032-1317709

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.
• Nucleophilic 5-endo-trig Cyclization of 3,3-Difluoroallylic Ketone Enolates: Synthesis of 5-Fluorinated 2-Alkylidene-2,3-dihydrofurans
  作者：Junji Ichikawa、Takeshi Fujita、Kotaro Sakoda、Masahiro Ikeda、Masahiro Hattori

  DOI：10.1055/s-0032-1317709

  日期：——

  3,3-Difluoroallylic ketones readily undergo nucleophilic 5-endo-trig cyclization through their metal enolates to afford 5-fluorinated 2-alkylidene-2,3-dihydrofurans. O-Cyclization exclusively occurred via intramolecular substitution of the vinylic fluorines.