N'-[1-(2-Hex-1-ynyl-cyclohex-1-enyl)-meth-(E)-ylidene]-N,N-dimethyl-hydrazine | 566190-88-3

• 分子结构分类: 有机化合物
• 英文名称: N'-[1-(2-Hex-1-ynyl-cyclohex-1-enyl)-meth-(E)-ylidene]-N,N-dimethyl-hydrazine
• 英文别名: N-[(2-hex-1-ynylcyclohexen-1-yl)methylideneamino]-N-methylmethanamine
• CAS: 566190-88-3
• 化学式: C₁₅H₂₄N₂
• 分子量: 232.369
• InChiKey: RRZYSANFOOVAIT-UHFFFAOYSA-N

物化性质

• 沸点：
  326.8±52.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N'-[1-(2-Hex-1-ynyl-cyclohex-1-enyl)-meth-(E)-ylidene]-N,N-dimethyl-hydrazine 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 生成 3-[2-(Dimethylamino)-4,5,6,7-tetrahydroisoindol-1-yl]heptan-2-one
  参考文献：
  名称：

  Synthesis of Pyrroles through Coupling of Enyne-hydrazones with Fischer Carbene Complexes

  摘要：

  The coupling of enyne-imines with Fischer carbene complexes leads to the formation of alkenylpyrrole derivatives. Maximum yields of pyrrole adducts were obtained using N,N-dimethylhydrazones. A mechanism involving alkyne insertion followed by nucleophilic attack of the imine nitrogen at the intermediate alkenylcarbene complex was proposed.

  DOI：

  10.1021/ol034414j
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 16.0h， 生成 N'-[1-(2-Hex-1-ynyl-cyclohex-1-enyl)-meth-(E)-ylidene]-N,N-dimethyl-hydrazine
  参考文献：
  名称：

  Synthesis of Pyrroles through Coupling of Enyne-hydrazones with Fischer Carbene Complexes

  摘要：

  The coupling of enyne-imines with Fischer carbene complexes leads to the formation of alkenylpyrrole derivatives. Maximum yields of pyrrole adducts were obtained using N,N-dimethylhydrazones. A mechanism involving alkyne insertion followed by nucleophilic attack of the imine nitrogen at the intermediate alkenylcarbene complex was proposed.

  DOI：

  10.1021/ol034414j

文献信息

• Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes
  作者：Bishnu Dhakal、Lalith S.R. Gamage、Yanshi Zhang、James W. Herndon

  DOI：10.1016/j.tetlet.2017.02.070

  日期：2017.4

  Three-component coupling of Fischer carbene complexes, enyne aldehyde hydrazones, and electron-deficient alkynes leads to simple benzoate derivatives in a process involving the formation of an N-aminopyrrole derivative, Diels-Alder reaction, and nitrene extrusion. The products are readily converted into isoquinolones through reaction with primary amines. The reaction proceeds best with highly substituted

  Fischer卡宾配合物，烯炔醛和电子缺乏炔烃的三组分偶联在形成N-氨基吡咯衍生物，Diels-Alder反应和氮烯挤出的过程中会生成简单的苯甲酸酯衍生物。通过与伯胺反应，产物易于转化为异喹诺酮。即使这些取代物是空间上最不利的底物，该反应也能以高度取代的且富含电子的吡咯进行得最好，并且这种反应性趋势得到了计算研究的支持。