5,6-(methylenedioxy)-2-propyl-2H-indazole | 138306-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5,6-(methylenedioxy)-2-propyl-2H-indazole
• 英文别名: 2-Propyl-2H,6H-[1,3]dioxolo[4,5-f]indazole；2-propyl-[1,3]dioxolo[4,5-f]indazole
• CAS: 138306-35-1
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: XHQLZYWAIPGFSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-硝基胡椒醛 在 bis-triphenylphosphine-palladium(II) chloride 、 tin(ll) chloride 一氧化碳 、 magnesium sulfate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 16.0h， 生成 5,6-(methylenedioxy)-2-propyl-2H-indazole
  参考文献：
  名称：

  Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives

  摘要：

  The dichlorobis(triphenylphosphine)palladium (PdCl2(PPh(3))(2))-tin(II) chloride (SnCl2) system shows high catalytic activity for the reductive N-heterocyclization of various 2-nitrostyrene and N-(2-nitrobenzylidene)amine derivatives when employed at 100 degrees C for 16 h under 20 kg cm(-2) of initial carbon monoxide pressure, to give the corresponding indole and 2H-indazole derivatives in good yield. For example, 2-phenylindole was obtained in 75% yield from the reductive N-heterocyclization of 2-nitrostilbene. Similarly, 2-propyl-2H-indazole was readily prepared in 83% yield by the reductive N-heterocyclization of N-(2-nitrobenzylidene)propylamine. A nitrene intermediate for the present reaction is proposed on the basis of deuterium-labeling experiments and the investigation of alkyl rearrangement in the construction of the indole skeleton. Carbon monoxide effectively operates as a deoxygenating agent of the nitro group to afford a nitrene intermediate.

  DOI：

  10.1021/jo00091a026

文献信息

• Palladium complex-catalysed reductive N-heterocyclization of N-(2-nitrobenzylidene)amines into 2H-indazole derivatives
  作者：Motohiro Akazome、Teruyuki Kondo、Yoshihisa Watanabe

  DOI：10.1039/c39910001466

  日期：——

  Dichlorobis(triphenylphosphine)palladium–tin(II) chloride system effectively catalyses the selective transformation of N-(2-nitrobenzylidene)amines into the corresponding 2H-indazole derivatives under carbon monoxide via a reductive N-heterocyclization reaction.

  二氯双(三苯基膦)氯化钯锡(II)体系能在一氧化碳条件下，通过还原性 N-杂环化反应，有效催化 N-(2-硝基亚苄基)胺向相应的 2H-indazole 衍生物的选择性转化。
• Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives
  作者：Motohiro Akazome、Teruyuki Kondo、Yoshihisa Watanabe

  DOI：10.1021/jo00091a026

  日期：1994.6

  The dichlorobis(triphenylphosphine)palladium (PdCl2(PPh(3))(2))-tin(II) chloride (SnCl2) system shows high catalytic activity for the reductive N-heterocyclization of various 2-nitrostyrene and N-(2-nitrobenzylidene)amine derivatives when employed at 100 degrees C for 16 h under 20 kg cm(-2) of initial carbon monoxide pressure, to give the corresponding indole and 2H-indazole derivatives in good yield. For example, 2-phenylindole was obtained in 75% yield from the reductive N-heterocyclization of 2-nitrostilbene. Similarly, 2-propyl-2H-indazole was readily prepared in 83% yield by the reductive N-heterocyclization of N-(2-nitrobenzylidene)propylamine. A nitrene intermediate for the present reaction is proposed on the basis of deuterium-labeling experiments and the investigation of alkyl rearrangement in the construction of the indole skeleton. Carbon monoxide effectively operates as a deoxygenating agent of the nitro group to afford a nitrene intermediate.