3-[3-(5-cyano-1H-indol-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-1H-indole-5-carbonitrile | 1193358-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[3-(5-cyano-1H-indol-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-1H-indole-5-carbonitrile
• 英文别名: 3,3-bis(5-cyano-1H-indol-3-yl)indolin-2-one；3,3-di(5-cyano-1H-indol-3-yl)indolin-2-one；3-[3-(5-cyano-1H-indol-3-yl)-2-oxo-1H-indol-3-yl]-1H-indole-5-carbonitrile
• CAS: 1193358-88-1
• 化学式: C₂₆H₁₅N₅O
• 分子量: 413.438
• InChiKey: IGBAPUDDQAPTAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氰基吲哚 、 靛红 在 zinc(II) oxide 作用下， 反应 2.0h， 以86%的产率得到3-[3-(5-cyano-1H-indol-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-1H-indole-5-carbonitrile
  参考文献：
  名称：

  氧化锌表面：多功能纳米平台，可无溶剂合成各种靛红衍生物

  摘要：

  在纳米结构的氧化锌表面上进行的多组分反应以优异的产率得到了3,3-双（吲哚基）吲哚-2-酮和x吨衍生物。氧化锌表面上的路易斯酸性位点（Zn 2+）和碱性位点（O 2-）均用于执行上述转化。通过使用表面掩蔽的氧化锌进行实验，进一步证明了表面催化的重要性。所开发的氧化锌纳米催化剂可重复使用多达五次，而活性没有明显损失。

  DOI：

  10.1016/j.tetlet.2016.06.094

文献信息

• Ruthenium-catalyzed efficient routes to oxindole derivatives
  作者：Khalil Tabatabaeian、Manouchehr Mamaghani、Nosratollah Mahmoodi、Alireza Khorshidi

  DOI：10.1139/v09-098

  日期：2009.9

  Ruthenium-catalyzed preparation of oxindoles from one-pot trimerization of indoles under oxidative conditions and from electrophilic substitution reaction of indoles with isatins or isatin-derived imines under very mild reaction conditions is reported.

  报告了钌催化制备氧化吲哚的过程，包括氧化条件下吲哚的一锅三聚反应，以及在非常温和的反应条件下吲哚与异汀或异汀衍生亚胺的亲电取代反应。
• Oxalic acid dihydrate: Proline (LTTM) as a new generation solvent for synthesis of 3,3-diaryloxindole and chromone based bis(indolyl)alkanes: Green, chromatography free protocol
  作者：Dattatray Chandam、Abhijeet Mulik、Prasad Patil、Suryabala Jagdale、Dayanand Patil、Sandeep Sankpal、Madhukar Deshmukh

  DOI：10.1016/j.molliq.2015.02.036

  日期：2015.7

  The new green approach has been used for the reaction of indole with various carbonyl compounds. The attractive features of this protocol are the use of green reaction medium, good to excellent product yields, operational simplicity, easy workup procedures and the use of group assistance purification process avoiding chromatographic purification. This protocol is expected to find application in the combinatorial synthesis of biologically active compounds, since indole and chromone motifs have a broad spectrum of biological activities. (C) 2015 Elsevier B.V. All rights reserved.
• Iodine-catalyzed condensation of isatin with indoles: A facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity
  作者：B.V. Subba Reddy、N. Rajeswari、M. Sarangapani、Y. Prashanthi、Roopa Jones Ganji、Anthony Addlagatta

  DOI：10.1016/j.bmcl.2012.02.011

  日期：2012.4

  Isatin reacts smoothly with indoles in the presence of a catalytic amount of molecular iodine under mild conditions to afford a novel class of di(indolyl)indolin-2-one derivatives in good yields. These molecules are found to possess a promising cytotoxicity against cancer cells only but not on normal cells. (C) 2012 Elsevier Ltd. All rights reserved.