2-amino-5-oxo-7,7-dimethylspiro[4H-5,6,7,8-tetrahydrochromene-4,3'-3'H-6'-bromoindol]-1'H-2'-one-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-5-oxo-7,7-dimethylspiro[4H-5,6,7,8-tetrahydrochromene-4,3'-3'H-6'-bromoindol]-1'H-2'-one-3-carbonitrile
• 英文别名: 2-amino-6'-bromo-1',2',5,6,7,8-hexahydro-7,7-dimethyl-2',5-dioxospiro[4H-1-benzopyran-4,3'-[3H]indole]-3-carbonitrile；2-Amino-6'-bromo-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile；2'-amino-6-bromo-7',7'-dimethyl-2,5'-dioxospiro[1H-indole-3,4'-6,8-dihydrochromene]-3'-carbonitrile
• 化学式: C₁₉H₁₆BrN₃O₃
• 分子量: 414.258
• InChiKey: FKYLWGUBWOUGLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-溴靛红 、 5,5-二甲基-1,3-环己二酮 、 丙二腈 在 12-tungstophosphoric acid supported on silica gel 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以84%的产率得到2-amino-5-oxo-7,7-dimethylspiro[4H-5,6,7,8-tetrahydrochromene-4,3'-3'H-6'-bromoindol]-1'H-2'-one-3-carbonitrile
  参考文献：
  名称：

  H3PW12O40: An Efficient Catalyst for the Synthesis of Spirooxindoles Under Ultrasound Irradiation

  摘要：

  以钨磷酸为催化剂，通过异汀、丙二腈和 1,3-二羰基化合物的反应，简单高效地实现了具有重要生物学意义的螺吲哚支架的三组份一锅合成。这种方法产量高、操作简便，因此具有重要价值。

  DOI：

  10.14233/ajchem.2013.14390

文献信息

• Multi-component supramolecular synthesis of spirooxindoles catalyzed by β-cyclodextrin in water
  作者：Regati Sridhar、Boga Srinivas、Bandaru Madhav、Vutukuri Prakash Reddy、Yadavalli Venkata Durga Nageswar、Kakulapati Rama Rao

  DOI：10.1139/v09-137

  日期：2009.12

  A neutral and efficient one-pot three-component aqueous-phase synthesis is developed for various spirooxindole derivatives from isatin, malononitrile, and 1,3-dicarbonyl compounds in high yields by supramolecular catalysis involving β-cyclodextrin. The β-cyclodextrin can be recovered and reused a number of times without any loss of activity.

  通过β-环糊精的超分子催化，开发了一种中性、高效的单锅三组分水相合成方法，可从异汀、丙二腈和 1,3-二羰基化合物中高产率地合成各种螺吲哚衍生物。β-环糊精可以多次回收和重复使用，而不会失去任何活性。
• A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium
  作者：Song-Lei Zhu、Shun-Jun Ji、Yong Zhang

  DOI：10.1016/j.tet.2007.06.113

  日期：2007.9

  A simple and efficient one-pot three-component synthesis of the biologically important spirooxindoles scaffold was carried out by the reaction of isatin, activated methylene reagent, and 1,3-dicarbonyl compounds in aqueous medium. This method is of great value because of its environmentally benign character, high yield processing, and easy handling.

  具有重要生物学意义的螺毒素平台的简单，有效的一锅三组分合成方法是通过使Isatin，活化的亚甲基试剂和1,3-二羰基化合物在水性介质中反应来进行的。该方法由于其对环境有益的特性，高产量的处理和易于处理而具有很大的价值。
• Efficient and Convenient Polyethylene Glycol (PEG)-Mediated Synthesis of Spiro-oxindoles
  作者：Harshadas Mitaram Meshram、Dachepally Aravind Kumar、Busam Ramalinga Vara Prasad、Palakuri Ramesh Goud

  DOI：10.1002/hlca.200900273

  日期：2010.4

  Polyethylene glycol (PEG) has been reported as an efficient and convenient medium for the three‐component synthesis for spiro‐oxindole.

  据报道，聚乙二醇（PEG）是螺-氧吲哚三组分合成的一种高效便捷的介质。
• An efficient one-pot three-component reaction for synthesis of spirooxindole derivatives in water media under catalyst-free condition
  作者：Li-Qin Zhao、Bo Zhou、Yi-Qun Li

  DOI：10.1002/hc.20723

  日期：2011.9

  An efficient, clean, and environmentally benign synthesis of spirooxindole derivatives by one-pot three-component reaction of isatins, malononitrile, and carbonyl compound in the absence of catalysis in water was described. A variety of spirooxindole derivatives were obtained with excellent yields within short reaction time. This novel protocol has the advantages of convenient operation, low cost,

  描述了在没有催化作用的情况下，通过靛红、丙二腈和羰基化合物的一锅三组分反应，高效、清洁和环境友好地合成螺吲哚衍生物。在很短的反应时间内以优异的产率获得了多种螺羟吲哚衍生物。这种新颖的协议具有操作方便、成本低、环境友好的优点。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:673–677, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20723
• Novel magnetic nanoparticles-supported inorganic-organic hybrids based on POSS as an efficient nanomagnetic catalyst for the synthesis of pyran derivatives
  作者：Javad Safaei-Ghomi、Seyed Hadi Nazemzadeh、Hossein Shahbazi-Alavi

  DOI：10.1016/j.catcom.2016.07.022

  日期：2016.11

  A new family of polyhedral oligomeric silsesquioxanes with eight triethoxysilane arms (APTPOSS) has been successfully anchored on the surface of Fe3O4 nanomagnetics and characterized by infrared spectroscopy, X-ray diffraction spectroscopy, scanning electron microscope, Energy Dispersive Spectroscopy, thermogravimetric analysis, dynamic light scattering and vibrating sample magnetometer. Fe3O4@APTPOSS, as a magnetic nanocatalyst for high-yield synthesis of pyrans has been employed. (C) 2016 Elsevier B.V. All rights reserved.