1-Phenyl-2-<2-(phenylethynyl)benzyl>pyrazolo<5,1-a>isoquinolin-6-one | 138308-55-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-Phenyl-2-<2-(phenylethynyl)benzyl>pyrazolo<5,1-a>isoquinolin-6-one
• 英文别名: 1-Phenyl-2-(2-(phenylethynyl)benzoyl)pyrazolo[5,1-a]isoquinolin-6(5H)-one；1-phenyl-2-[2-(2-phenylethynyl)benzoyl]-5H-pyrazolo[5,1-a]isoquinolin-6-one
• CAS: 138308-55-1
• 化学式: C₃₂H₂₀N₂O₂
• 分子量: 464.523
• InChiKey: ONEAINCCAAHHFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基乙炔基苯甲酸甲酯 在 potassium trimethylsilonate 、 氯甲酸甲酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 1-Phenyl-2-<2-(phenylethynyl)benzyl>pyrazolo<5,1-a>isoquinolin-6-one
  参考文献：
  名称：

  A comparative study of the decomposition of o-alkynyl-substituted aryl diazo ketones. Synthesis of polysubstituted .beta.-naphthols via arylketene intermediates

  摘要：

  The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl alpha-diazoaceto- and propiophenone derivatives have been studied. The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion. Thermolysis or photolysis of o-alkynyl alpha-diazopropiophenone derivatives yields polysubstituted beta-naphthols. These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynyl substituent. In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered pi-system producing a vinyl carbenoid intermediate. Further reaction of the cyclized carbenoid with the starting diazo compound furnishes a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis. Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.

  DOI：

  10.1021/jo00075a045

文献信息

• Rearrangement of o-alkynyl substituted α-diazoacetophenones. Conversion to β-naphthols via arylketene intermediates
  作者：Albert Padwa、David J. Austin、Ugo Chiacchio、Jamal M. Kassir、Antonio Rescifina、Simon L. Xu

  DOI：10.1016/s0040-4039(00)79427-5

  日期：1991.10

  In contrast to the rhodium (II) mediated cycloisomerization of o-alkynyl substituted α-diazoacetophenones, irradiation leads to β-naphthols which are formed via cyclization of an arylketene intermediate.

  与铑（II）介导的邻炔基取代的α-二重氮苯乙酮的环异构化相反，辐射导致生成β-萘酚，后者是通过芳基烯酮中间体的环化反应而形成的。
• Padwa Albert, Chiacchio Ugo, Fairfax David J., Kassir Jamal M., Litrico A+, J. Org. Chem, 58 (1993) N 23, S 6429-6437
  作者：Padwa Albert, Chiacchio Ugo, Fairfax David J., Kassir Jamal M., Litrico A+

  DOI：——

  日期：——
• A comparative study of the decomposition of o-alkynyl-substituted aryl diazo ketones. Synthesis of polysubstituted .beta.-naphthols via arylketene intermediates
  作者：Albert Padwa、Ugo Chiacchio、David J. Fairfax、Jamal M. Kassir、Angelo Litrico、Mark A. Semones、Simon L. Xu

  DOI：10.1021/jo00075a045

  日期：1993.11

  The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl alpha-diazoaceto- and propiophenone derivatives have been studied. The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion. Thermolysis or photolysis of o-alkynyl alpha-diazopropiophenone derivatives yields polysubstituted beta-naphthols. These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynyl substituent. In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered pi-system producing a vinyl carbenoid intermediate. Further reaction of the cyclized carbenoid with the starting diazo compound furnishes a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis. Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.