3-(4-(diphenylamino)phenyl)isobenzofuran-1(3H)-one | 1115589-32-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-(diphenylamino)phenyl)isobenzofuran-1(3H)-one
• 英文别名: 3-[4-(N-phenylanilino)phenyl]-3H-2-benzofuran-1-one
• CAS: 1115589-32-6
• 化学式: C₂₆H₁₉NO₂
• 分子量: 377.442
• InChiKey: IYWYYNAWNUIKFP-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  562.3±50.0 °C(predicted)
• 密度：
  1.252±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-(diphenylamino)phenyl)isobenzofuran-1(3H)-one 在 sodium tetrahydroborate 、 lead(IV) tetraacetate 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  涉及路易斯酸介导的不对称1,2-（二芳基/二杂芳基甲胺）二戊酸酯的路易斯选择性环化芳烃和杂芳烃的合成

  摘要：

  室温下，DCM中ZnBr 2介导的不对称1,2-二芳基次甲基新戊二酸酯的区域选择性环化导致环化的芳烃和杂芳烃的形成。二戊酸酯的环化通过苄基碳阳离子的中间进行，然后进行分子内环化和随后的芳构化，以得到环化的产物。对于蒽和萘并[ b ]噻吩类似物的合成，环空方法学是非常有效的。

  DOI：

  10.1021/jo301410w
• 作为产物：
  描述：

  三苯胺 在 aluminum (III) chloride 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-(4-(diphenylamino)phenyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Bistriphenylamine-substituted fluoranthene derivatives as electroluminescent emitters and dye-sensitized solar cells

  摘要：

  A novel series of compounds containing fluoranthene and triphenylamine were designed and synthesized as electroluminescent materials or sensitizers. Photophysical and electrochemical measurements were carried out on these compounds. DPBF exhibited a maximum current efficiency of 1.3 cd/A (1.00 lm/W at 5.17 V) and D2 had the maximum light-to-electricity efficiency of 4.57% under AM 1.5 solar simulator (100 mW cm(-2)). The results suggest that bistriphenylamine-substituted fluoranthene derivatives have the potential application in optoelectronic materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.013

文献信息

• Synthesis of Annulated Arenes and Heteroarenes by Hydriodic Acid and Red Phosphorus Mediated Reductive Cyclization of 2-(Hetero)aroylbenzoic Acids or 3-(Hetero)arylphthalides
  作者：Arasambattu Mohanakrishnan、Settu Rafiq

  DOI：10.1055/s-0036-1588337

  日期：——

  Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.

  通过氢碘酸/红磷介导的 3-（杂）芳基苯酞的还原环化，以良好到非常好的产率制备了环化芳烃和杂环芳烃。2-芳酰基苯甲酸和2-芳酰基萘甲酸也成功地进行了还原环化。
• Oxidative Ring Opening of 1,3-Diarylbenzo[c]heterocycles Using m-CPBA: Preparation of 1,2-Diaroylbenzenes
  作者：Meganathan Nandakumar、Ramakrishnan Sivasakthikumaran、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201200311

  日期：2012.7

  An unprecedented oxidative cleavage of benzo[c]heterocycles using m-CPBA is reported. The reaction of 1,3-diaryl benzo[c]heterocycles with m-CPBA (meta-chloroperoxybenzoic acid) at room temperature for 5 min led to the formation of 1,2-diaroylbenzenes in good to excellent yields.

  报道了使用 m-CPBA 对苯并 [c] 杂环进行前所未有的氧化裂解。1,3-二芳基苯并 [c] 杂环与 m-CPBA（间氯过氧苯甲酸）在室温下反应 5 分钟，以良好到极好的产率形成 1,2-二芳基苯。
• Synthesis and characterization of benzo[c]thiophene analogs tethered with dibenzo-heterocycles as potential OLEDs
  作者：Natarajan Senthil Kumar、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2008.11.044

  日期：2009.1

  Synthesis of mixed heterocyclic system containing benzo[c]thiophene, dibenzo-heterocycles, and thiophene unit is described.

  描述了含有苯并[ c ]噻吩，二苯并杂环和噻吩单元的混合杂环系统的合成。
• Studies on the Phthalidation of Heteroarenes: A Facile Preparation of 3-(Heteroaryl)phthalides via Triflic Acid Mediated Phthalidation
  作者：Arasambattu Mohanakrishnan、Meganathan Nandakumar、Elumalai Sankar

  DOI：10.1055/s-0033-1340551

  日期：——

  A triflic acid mediated heteroarylation of phthalaldehydic acid in 1,2-dichloroethane at reflux temperature leads to the formation of 3-heteroarylphthalides. This method for the phthalidation of heteroarenes can be utilized for the successful preparation of mono-, bis- and tris-heteroarylphthalides.
• Synthesis of Annulated Arenes and Heteroarenes Involving Lewis Acid-Mediated Regioselective Annulation of Unsymmetrical 1,2-(Diaryl/diheteroarylmethine)dipivalates
  作者：Ramakrishnan Sivasakthikumaran、Meganathan Nandakumar、Arasambattu K. Mohanakrishnan

  DOI：10.1021/jo301410w

  日期：2012.10.19

  A ZnBr2-mediated regioselective annulation of unsymmetrical 1,2-diarylmethinedipivalates in DCM at room temperature led to the formation of annulated arenes and heteroarenes. The annulation of the dipivalate proceeds through the intermediacy of benzylic carbocations followed by intramolecular cyclization and subsequent aromatization to give the annulated products. The annulation methodology is highly

  室温下，DCM中ZnBr 2介导的不对称1,2-二芳基次甲基新戊二酸酯的区域选择性环化导致环化的芳烃和杂芳烃的形成。二戊酸酯的环化通过苄基碳阳离子的中间进行，然后进行分子内环化和随后的芳构化，以得到环化的产物。对于蒽和萘并[ b ]噻吩类似物的合成，环空方法学是非常有效的。