Phenyl-carbamic acid 6H-5-oxa-benzo[c]phenanthren-7-yl ester | 138308-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: Phenyl-carbamic acid 6H-5-oxa-benzo[c]phenanthren-7-yl ester
• 英文别名: 6H-naphtho[2,1-c]chromen-7-yl N-phenylcarbamate
• CAS: 138308-63-1
• 化学式: C₂₄H₁₇NO₃
• 分子量: 367.404
• InChiKey: PJMCMQJYFULLLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6H-Benzonaphtho<1,2-d>pyran-7-ol 、 异氰酸苯酯 生成 Phenyl-carbamic acid 6H-5-oxa-benzo[c]phenanthren-7-yl ester
  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

文献信息

• 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.
• 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：——