4-[5-Methoxy-3-(triethylsilyloxymethyl)indazol-2-yl]benzonitrile | 1027304-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[5-Methoxy-3-(triethylsilyloxymethyl)indazol-2-yl]benzonitrile
• CAS: 1027304-19-3
• 化学式: C₂₂H₂₇N₃O₂Si
• 分子量: 393.561
• InChiKey: ICGUUGIFRJMONO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[5-Methoxy-3-(triethylsilyloxymethyl)indazol-2-yl]benzonitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以0.21 g的产率得到2-(4-cyanophenyl)-3-hydroxymethyl-5-methoxy-2H-indazole
  参考文献：
  名称：

  Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes

  摘要：

  A new route to substituted 2-phenyl-2H-indazoIes through the cyclization of (2-ethynylphenyl)-phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a [2 + 1] cycloadduct with 2,3-dimethyl-2-butene.

  DOI：

  10.1021/jo049011r
• 作为产物：
  描述：

  3-碘苯酚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 盐酸 、 氢氧化钾 、 copper(l) iodide 、 四丁基氟化铵 、 caesium carbonate 、 二异丙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 46.5h， 生成 4-[5-Methoxy-3-(triethylsilyloxymethyl)indazol-2-yl]benzonitrile
  参考文献：
  名称：

  Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes

  摘要：

  A new route to substituted 2-phenyl-2H-indazoIes through the cyclization of (2-ethynylphenyl)-phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a [2 + 1] cycloadduct with 2,3-dimethyl-2-butene.

  DOI：

  10.1021/jo049011r