2-phenylimino-1,3-indandione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenylimino-1,3-indandione
• 英文别名: 2-Phenyliminoindene-1,3-dione
• 化学式: C₁₅H₉NO₂
• 分子量: 235.242
• InChiKey: JPAPSRZOOKRCDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylimino-1,3-indandione 、 (三苯基膦烯)乙烯酮 以 甲苯 为溶剂， 反应 10.0h， 以77%的产率得到1-phenyl-2-(oxo)-3-(triphenylphosphoranylidene)spiro[azetidine-2,2'-(2H)-indene]1',3'-dione
  参考文献：
  名称：

  磷叶立德化学 21 合成氮杂环丁酮的新路线。鏻叶立德与苯偶酰、邻萘醌和三酮单苯胺的反应

  摘要：

  Active vinylidenetriphenylphosphoranes are nucleophilic reagents which can be considered as versatile synthons for the synthesis of new heterocycles. The active phosphacumulene ylides, namely N-phenylimino-2a, 2-oxo-2b or 2-thioxovinylidenetriphenylphosphoranes (2c), react with benzil-(1a,b), o-naphthoquinone-(8), or triketonemonoanils (11), to give the corresponding phenylimino- (3a, d, 9a, 12a), oxo-(3b, e, 9b, 12b), or thioxoazetidinones (3c, f, 9c, 12c), respectively, which constitute an important class of organic compounds with medicinal and biological importance. On the other hand, quinone monoanils la, 8, 11 can be converted by reaction with the stabilized alkylidenephosphoranes (5a-d), namely acetylmethylene-5a, methoxycarbonylmethylene-5b, ethoxycarbonylmethylene-5c, and benzoylmethylenetriphenylphosphorane 5d, into the phosphoranylidenes (7a-d, 10a-d, 13a-d). No reaction was observed between iminophosphorane (14) and the monoanil (11). The structures of the new products were assigned according to consistent analytical and spectroscopic data. (c) 2005 Wiley Periodicals, Inc.

  DOI：

  10.1002/hc.20144
• 作为产物：
  描述：

  1,2,3-茚满三酮 、 苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-phenylimino-1,3-indandione
  参考文献：
  名称：

  铜催化一锅法、三组分非对映选择性合成 3-Spiroazetidinimine-2-oxindoles 及其合成转化为荧光共轭吲哚酮

  摘要：

  一种简便高效的铜 (I) 催化一锅、三组分非对映选择性合成已完成，该合成以优异的收率提供了新的 3-spiroazetinimine-2-oxindoles。通过在碱性条件下用 KOH/MeOH 和对硫甲酚处理，3-spiroazetidinimine-2-oxindoles 经历了 spiroazetidinimine 单元的轻松开环反应，以提供两类新的荧光共轭吲哚酮。该方法对于衍生自 9-芴酮、1,2-二酮和 1,2,3-三酮的亚胺具有普遍应用。

  DOI：

  10.1002/ejoc.201301244

文献信息

• A Copper-Catalyzed One-Pot, Three-Component Diastereoselective Synthesis of 3-Spiroazetidinimine-2-oxindoles and Their Synthetic Transformation into Fluorescent Conjugated Indolones
  作者：Somasundharam Periyaraja、Ponnusamy Shanmugam、Asit Baran Mandal

  DOI：10.1002/ejoc.201301244

  日期：2014.2

  copper(I)-catalyzed one-pot, three-component diastereoselective synthesis that provides new 3-spiroazetidinimine-2-oxindoles in excellent yield has been accomplished. The 3-spiroazetidinimine-2-oxindoles underwent a facile ring-opening reaction of the spiroazetidinimine unit by treatment with KOH/MeOH and p-thiocresol under basic conditions to afford two new classes of fluorescent conjugated indolones. This method

  一种简便高效的铜 (I) 催化一锅、三组分非对映选择性合成已完成，该合成以优异的收率提供了新的 3-spiroazetinimine-2-oxindoles。通过在碱性条件下用 KOH/MeOH 和对硫甲酚处理，3-spiroazetidinimine-2-oxindoles 经历了 spiroazetidinimine 单元的轻松开环反应，以提供两类新的荧光共轭吲哚酮。该方法对于衍生自 9-芴酮、1,2-二酮和 1,2,3-三酮的亚胺具有普遍应用。
• Chemistry of phosphorus ylides 21 new route for the synthesis of azetidinones. Reaction of phosphonium ylides with benzil-,o-naphthoquinone-, and triketonemonoanils
  作者：Fouad M. Soliman、Medhat M. Said、Soher S. Maigali

  DOI：10.1002/hc.20144

  日期：——

  Active vinylidenetriphenylphosphoranes are nucleophilic reagents which can be considered as versatile synthons for the synthesis of new heterocycles. The active phosphacumulene ylides, namely N-phenylimino-2a, 2-oxo-2b or 2-thioxovinylidenetriphenylphosphoranes (2c), react with benzil-(1a,b), o-naphthoquinone-(8), or triketonemonoanils (11), to give the corresponding phenylimino- (3a, d, 9a, 12a), oxo-(3b, e, 9b, 12b), or thioxoazetidinones (3c, f, 9c, 12c), respectively, which constitute an important class of organic compounds with medicinal and biological importance. On the other hand, quinone monoanils la, 8, 11 can be converted by reaction with the stabilized alkylidenephosphoranes (5a-d), namely acetylmethylene-5a, methoxycarbonylmethylene-5b, ethoxycarbonylmethylene-5c, and benzoylmethylenetriphenylphosphorane 5d, into the phosphoranylidenes (7a-d, 10a-d, 13a-d). No reaction was observed between iminophosphorane (14) and the monoanil (11). The structures of the new products were assigned according to consistent analytical and spectroscopic data. (c) 2005 Wiley Periodicals, Inc.