o-(3-Phenoxy-1-propynyl)-α-diazoacetophenone | 138308-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: o-(3-Phenoxy-1-propynyl)-α-diazoacetophenone
• 英文别名: 2-diazonio-1-[2-(3-phenoxyprop-1-ynyl)phenyl]ethenolate
• CAS: 138308-58-4
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: USNQUORAYAULFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  o-(3-Phenoxy-1-propynyl)-α-diazoacetophenone 以 二氯甲烷 为溶剂， 以70%的产率得到6H-Benzonaphtho<1,2-d>pyran-7-ol
  参考文献：
  名称：

  邻炔基取代的α-重氮苯乙酮的重排。通过芳基烯酮中间体转化为β-萘酚

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)79427-5
• 作为产物：
  描述：

  苯基炔丙基醚 在 trans-bis(triphenylphosphine)palladium(II) chloride 、 potassium trimethylsilonate 、 copper(II) iodide 、 三乙胺 、 氯甲酸甲酯 作用下， 以 乙醚 为溶剂， 反应 32.0h， 生成 o-(3-Phenoxy-1-propynyl)-α-diazoacetophenone
  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

• 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：——