3,3-bis(2-phenyl-1H-indol-3-yl)indolin-2-one | 1122643-97-3

• 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-bis(2-phenyl-1H-indol-3-yl)indolin-2-one
• 英文别名: 3,3-bis(2-phenyl-1H-indol-3-yl)-1H-indol-2-one
• CAS: 1122643-97-3
• 化学式: C₃₆H₂₅N₃O
• 分子量: 515.614
• InChiKey: PNFIBADMGRMPEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯基吲哚 、 靛红 在 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以85%的产率得到3,3-bis(2-phenyl-1H-indol-3-yl)indolin-2-one
  参考文献：
  名称：

  Zn(OTf)2-catalysed indolylation and pyrrolylation of isatins: Efficient synthesis and biochemical assay of 3,3-di(heteroaryl)oxindoles

  摘要：

  通过Zn(OTf)2催化的吲哚化和吡咯化反应，开发出一种高效且经济的3,3-双(吲哚基)氧吲哚和3,3-双(吡咯基)氧吲哚合成方法。在啮齿类动物模型中对合成的分子进行了初步的生化检测，以评估其血清谷氨酸草酰乙酸转氨酶和丙二醛水平。

  DOI：

  10.1007/s12039-013-0510-y

文献信息

• Efficient synthesis of 3-substituted indoles through a domino gold(I) chloride catalyzed cycloisomerization/C3-functionalization of 2-(alkynyl)anilines
  作者：C. Praveen、K. Karthikeyan、P.T. Perumal

  DOI：10.1016/j.tet.2009.09.019

  日期：2009.11

  An efficient synthesis of 3-substituted indoles by a sequential approach involving gold(I) chloride catalyzed cycloisomerization/bis-addition and conjugate addition of 2-(alkynyl)anilines has been accomplished. A variety of 2-(alkynyl)anilines, aldehydes, isatins and nitroolefins undergo this overall process in good to excellent yields. This methodology represents an effective alternative to the classical

  通过包括氯化金（I）催化的环异构化/双加成和2-（炔基）苯胺的共轭加成的顺序方法，已经完成了3-取代的吲哚的有效合成。各种2-（炔基）苯胺，醛，靛红和硝基烯烃以良好或优异的收率经历了整个过程。这种方法代表了吲哚经典C3功能化的有效替代方法。
• Gold(I)-catalyzed sequential cycloisomerization/bis-addition of o-ethynylanilines: an efficient access to bis(indolyl)methanes and di(indolyl)indolin-2-ones
  作者：C. Praveen、Y. Wilson Sagayaraj、P.T. Perumal

  DOI：10.1016/j.tetlet.2008.11.086

  日期：2009.2

  An efficient synthesis of bis(indolyl)methanes and di(indolyl)indolin-2-ones has been developed by a sequential approach involving gold(I)-catalyzed cycloisomerization/bis-addition of o-ethynylanilines with various aldehydes and isatins, respectively. This methodology opens clean and synthetically competitive alternative to the already established procedures of the synthesis of bis(indolyl)methanes

  通过顺序方法已经开发了有效的合成双（吲哚基）甲烷和二（吲哚基）吲哚-2-酮的方法，该方法涉及金（I）催化的邻乙炔基苯胺的环异构化/双加成分别与各种醛和靛红。这种方法为合成双（吲哚基）甲烷和二（吲哚基）吲哚啉-2-酮的既定方法提供了清洁的，具有合成竞争力的替代方法。
• One-pot synthesis of spirofluorenyl- and spiroindeno[1,2-b]indolyl oxindoles via sequential inter- and intramolecular Friedel–Crafts reactions
  作者：Jin Woo Lim、Hye Ran Moon、Su Yeon Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2015.11.080

  日期：2016.1

  Various spirofluorenyl oxindoles and spiroindeno[1,2-b]indolyl oxindoles were synthesized in good yields in one-pot reaction by TiCl4-catalyzed sequential inter- and intramolecular Friedel-Crafts reactions of isatins with meta-arylphenols and 2-arylindoles in 1,2-dichloroethane. (C) 2015 Elsevier Ltd. 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.
• Zn(OTf)2-catalysed indolylation and pyrrolylation of isatins: Efficient synthesis and biochemical assay of 3,3-di(heteroaryl)oxindoles
  作者：C PRAVEEN、S NARENDIRAN、P DHEENKUMAR、P T PERUMAL

  DOI：10.1007/s12039-013-0510-y

  日期：2013.11

  An efficient and cheap synthetic approach to 3,3-di(indolyl)oxindoles and 3,3-di(pyrrolyl)oxindoles has been developed via Zn(OTf)2 catalysed indolylation and pyrrolylation of isatins. A preliminary biochemical assay of the synthesized molecules in rodent models were performed to estimate the serum glutamate oxaloacetate transaminase and malondialdehyde levels.

  通过Zn(OTf)2催化的吲哚化和吡咯化反应，开发出一种高效且经济的3,3-双(吲哚基)氧吲哚和3,3-双(吡咯基)氧吲哚合成方法。在啮齿类动物模型中对合成的分子进行了初步的生化检测，以评估其血清谷氨酸草酰乙酸转氨酶和丙二醛水平。