3-cyclohexyl-2,2-dimethyl-3-oxopropanal | 89635-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyclohexyl-2,2-dimethyl-3-oxopropanal
• CAS: 89635-69-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: YNSROXPZXLMYHS-UHFFFAOYSA-N

物化性质

• 沸点：
  262.8±23.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclohexyl-2,2-dimethyl-3-oxopropanal 在 potassium hydride 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 33.25h， 生成 2-cyclohexylidene-5-fluoro-3,3-dimethyl-2,3-dihydrofuran
  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：

  环己甲酰氯 在 正丁基锂 、 草酸 、 二异丙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 15.42h， 生成 3-cyclohexyl-2,2-dimethyl-3-oxopropanal
  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

• DITGENS, K.;KRAEMER, W.;ELBE, H. -L.
  作者：DITGENS, K.、KRAEMER, W.、ELBE, H. -L.

  DOI：——

  日期：——
• 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.