2-(4-bromophenyl)-3-hydroxymethyl-5-methoxy-2H-indazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-bromophenyl)-3-hydroxymethyl-5-methoxy-2H-indazole
• 英文别名: [2-(4-Bromophenyl)-5-methoxyindazol-3-yl]methanol
• 化学式: C₁₅H₁₃BrN₂O₂
• 分子量: 333.184
• InChiKey: GHRMIHNXUHFCNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 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 2-(4-bromophenyl)-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

文献信息

• Experimental and Theoretical Investigation of the Coarctate Cyclization of (2-Ethynylphenyl)phenyldiazenes
  作者：Laura D. Shirtcliff、Timothy J. R. Weakley、Michael M. Haley、Felix Köhler、Rainer Herges

  DOI：10.1021/jo049011r

  日期：2004.10.1

  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.