3-Ethynyl-5-methyl-2-phenylindazole | 1404166-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Ethynyl-5-methyl-2-phenylindazole
• CAS: 1404166-06-8
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: CHOLWGUTRIJYKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3,3-Diethyl-1-(2-iodo-4-methylphenyl)triaz-1-ene 、 3-Ethynyl-5-methyl-2-phenylindazole 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到N-ethyl-N-[[4-methyl-2-[2-(5-methyl-2-phenylindazol-3-yl)ethynyl]phenyl]diazenyl]ethanamine
  参考文献：
  名称：

  Doubly Coarctate-Stabilized Carbenes: Synthetic and Computational Studies

  摘要：

  Isoindazoles joined by an ethynyl linker to either a phenyltriazene or a phenyldiazene moiety were synthesized, and their subsequent reactivity was examined. Computations suggest that these molecules could rearrange at moderate temperatures via carbene intermediates that are doubly stabilized by coarctate conjugation. The experimental results corroborate the calculations, as the transient carbene can either be trapped with oxygen or undergo ring opening to afford a rearranged product Additional calculations illustrate some design principles that might lead to stable carbenes that are the global minimum on the coarctate hypersurface.

  DOI：

  10.1021/jo3020374
• 作为产物：
  描述：

  3-hydroxymethyl-5-methyl-2-phenyl-2H-indazole 在 manganese(IV) oxide 、 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 16.67h， 生成 3-Ethynyl-5-methyl-2-phenylindazole
  参考文献：
  名称：

  Doubly Coarctate-Stabilized Carbenes: Synthetic and Computational Studies

  摘要：

  Isoindazoles joined by an ethynyl linker to either a phenyltriazene or a phenyldiazene moiety were synthesized, and their subsequent reactivity was examined. Computations suggest that these molecules could rearrange at moderate temperatures via carbene intermediates that are doubly stabilized by coarctate conjugation. The experimental results corroborate the calculations, as the transient carbene can either be trapped with oxygen or undergo ring opening to afford a rearranged product Additional calculations illustrate some design principles that might lead to stable carbenes that are the global minimum on the coarctate hypersurface.

  DOI：

  10.1021/jo3020374