3-hydroxymethyl-2-phenyl-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: 3-hydroxymethyl-2-phenyl-2H-indazole
• 英文别名: (2-phenyl-2H-indazol-3-yl)methanol；(2-Phenylindazol-3-yl)methanol
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: XVUAXYNXXZUFNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-phenyl-3-triethylsilyloxymethyl-2H-indazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以67 mg的产率得到3-hydroxymethyl-2-phenyl-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

• Synthesis of (2<i>H</i>)-Indazoles and Dihydrocinnolinones through Annulation of Azobenzenes with Vinylene Carbonate under Rh(III) Catalysis
  作者：Min Seo Park、Kyeongwon Moon、Harin Oh、Ji Yoon Lee、Prithwish Ghosh、Ju Young Kang、Jung Su Park、Neeraj Kumar Mishra、In Su Kim

  DOI：10.1021/acs.orglett.1c01866

  日期：2021.7.16
• 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.