2-amino-4-(5-chloro-1H-indol-3-yl)-4H-chromene-3-carbonitrile

• 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: 2-amino-4-(5-chloro-1H-indol-3-yl)-4H-chromene-3-carbonitrile
• 化学式: C₁₈H₁₂ClN₃O
• 分子量: 321.766
• InChiKey: ZQZBNDDQPOOKQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-cyano-2-iminocoumarin 、 5-氯吲哚 在 三乙胺 作用下， 生成 2-amino-4-(5-chloro-1H-indol-3-yl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Facile synthesis of chiral 2-amino-4-(indol-3-yl)-4H-chromene derivatives using thiourea as the catalyst

  摘要：

  The enantioselective Friedel-Crafts alkylation of indoles with iminochromenes catalyzed by a bifunctional thiourea organocatalyst was investigated. This reaction afforded chiral functionalized 2-amino-4-(indol-3-yl)-4H-chromenes in good yields (up to 87% yield) and with moderate to good enantioselectivities (up to 86% ee). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.018

文献信息

• An eco-friendly synthesis of 2-aminochromenes and indolyl chromenes catalyzed by InCl3 in aqueous media
  作者：Gnanamani Shanthi、Paramasivan T. Perumal

  DOI：10.1016/j.tetlet.2007.07.102

  日期：2007.9

  A simple and convenient method for the synthesis of new 2-aminochromenes and indolyl chromenes via an indium trichloride catalyzed, three-component reaction in aqueous media is described.

  描述了一种简单方便的方法，用于在水性介质中通过三氯化铟催化的三组分反应合成新的2-氨基色烯和吲哚基色烯。
• β-Cyclodextrin: A Biomimetic Catalyst used for the Synthesis of 4H-chromene-3-carbonitrile and Tetrahydro-1H-xanthen-1-one Derivatives
  作者：Pratibha Rai、Madhulika Srivastava、Snehlata Yadav、Jaya Singh、Jagdamba Singh

  DOI：10.1007/s10562-015-1588-2

  日期：2015.12

  An efficient and facile protocol has been documented for the synthesis of 4H-chromene and xanthen-1-one derivatives via a three component one pot reaction of salicyladehyde, malononitrile/dimedone and indole utilizing biomimetic catalyst. Affiliation between biomimetic and organocatalyst exhibits a versatile and high catalytic activity emerging to be a sustainable alternative to other catalysts. The significant features of this protocol are compatibility with various types of indole and active-methylene compound, accomplishment of high yields, cleaner reaction condition and avoidance of the use of costly catalysts. Recyclability of beta-cyclodextrin a "biomimetic catalyst" is a significant feature of this protocol.
• Shanthi, Gnanamani; Perumal, Paramasivan T.; Rao, Urmila, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 9, p. 1319 - 1323
  作者：Shanthi, Gnanamani、Perumal, Paramasivan T.、Rao, Urmila、Sehgal, Praveen Kumar

  DOI：——

  日期：——
• Facile synthesis of chiral 2-amino-4-(indol-3-yl)-4H-chromene derivatives using thiourea as the catalyst
  作者：Yu Gao、Da-Ming Du

  DOI：10.1016/j.tetasy.2013.08.018

  日期：2013.10

  The enantioselective Friedel-Crafts alkylation of indoles with iminochromenes catalyzed by a bifunctional thiourea organocatalyst was investigated. This reaction afforded chiral functionalized 2-amino-4-(indol-3-yl)-4H-chromenes in good yields (up to 87% yield) and with moderate to good enantioselectivities (up to 86% ee). (C) 2013 Elsevier Ltd. All rights reserved.