7,8-Dihydrobenzophenanthren-6-ol | 138308-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7,8-Dihydrobenzophenanthren-6-ol
• 英文别名: 7,8-Dihydrobenzo[c]phenanthren-6-ol
• CAS: 138308-61-9
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: GVEKVUXOODDLNH-UHFFFAOYSA-N

物化性质

• 沸点：
  449.3±24.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,8-Dihydrobenzophenanthren-6-ol 在 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 168.0h， 生成 6-methoxybenzophenanthrene
  参考文献：
  名称：

  内-外环1,3-双（三甲基甲硅烷氧基）-1,3-二烯作为螺旋合成中的有用中间体

  摘要：

  基于内外环1,3-bis（-）之间的狄尔斯-阿尔德反应的新颖合成方法，从四氢萘酮和四氢菲蒽酮化合物通过五步合成了功能化的苯并[ c ]菲（[4]螺旋）和[5]三甲基甲硅烷氧基）-1,3-二烯和苯炔或醌。

  DOI：

  10.1016/s0040-4039(02)02246-3
• 作为产物：
  描述：

  邻溴苯甲酸甲酯 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 、 二氯甲烷 为溶剂， 反应 32.33h， 生成 7,8-Dihydrobenzophenanthren-6-ol
  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：——
• CHROMENE COMPOUND
  申请人：Tokuyama Corporation

  公开号：EP2275418B1

  公开（公告）日：2012-10-17
• US8147726B2
  申请人：——

  公开号：US8147726B2

  公开（公告）日：2012-04-03
• US8308995B2
  申请人：——

  公开号：US8308995B2

  公开（公告）日：2012-11-13