4-(4-acetylphenyl)-3-phenylsydnone | 1225057-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-acetylphenyl)-3-phenylsydnone
• 英文别名: 4-(4-Acetylphenyl)-3-phenyloxadiazol-3-ium-5-olate
• CAS: 1225057-56-6
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: NSWXSEDDXJMUDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-acetylphenyl)-3-phenylsydnone 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以71%的产率得到1-(4-(2-phenyl-2H-indazol-3yl)phenyl)ethanone
  参考文献：
  名称：

  Synthesis of 2H-Indazoles by the [3 + 2] Cycloaddition of Arynes and Sydnones

  摘要：

  A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.

  DOI：

  10.1021/ol100586r
• 作为产物：
  描述：

  N-苯基甘氨酸 在 palladium diacetate 、 乙酸酐 、 potassium carbonate 、 三苯基膦 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 4-(4-acetylphenyl)-3-phenylsydnone
  参考文献：
  名称：

  Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

  摘要：

  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.

  DOI：

  10.1021/jo201605v

文献信息

• Synthesis of 2<i>H</i>-Indazoles by the [3 + 2] Cycloaddition of Arynes and Sydnones
  作者：Chunrui Wu、Yuesi Fang、Richard C. Larock、Feng Shi

  DOI：10.1021/ol100586r

  日期：2010.5.21

  A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.
• Synthesis of 2<i>H</i>-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
  作者：Yuesi Fang、Chunrui Wu、Richard C. Larock、Feng Shi

  DOI：10.1021/jo201605v

  日期：2011.11.4

  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.