6'‑amino‑3'‑methyl‑2‑oxo-1'‑phenyl‑1'H‑spiro[5‑nitroindoline‑3,4'‑pyrano[2,3‑c]pyrazole]‑5'‑carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6'‑amino‑3'‑methyl‑2‑oxo-1'‑phenyl‑1'H‑spiro[5‑nitroindoline‑3,4'‑pyrano[2,3‑c]pyrazole]‑5'‑carbonitrile
• 英文别名: 6'-amino-3'-methyl-5-nitro-2-oxo-1'-phenyl-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-3'-methyl-2-oxo-1'-phenyl-1'H-spiro[5-nitroindoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-5'-cyano-3'-methyl-1'-phenyl-5-nitrospiro[indoline-3,4'(1'H)-pyrano[2,3-c]pyrazole]-2-one；6'-amino-5'-cyano-3'-methyl-5-nitro-1'-phenylspiro[indoline-3,4'(1H')-pyrano[2,3-c]pyrazol]-2-one；6'-amino-3'-methyl-5-nitro-2-oxo-1'-phenyl-1,2-dihydro-1'H-spiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-3'-methyl-5-nitro-2-oxo-1'-phenylspiro[1H-indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 化学式: C₂₁H₁₄N₆O₄
• 分子量: 414.38
• InChiKey: NHJZQHICYBEZPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-硝基靛红 在 aluminum oxide 作用下， 反应 0.1h， 生成 6'‑amino‑3'‑methyl‑2‑oxo-1'‑phenyl‑1'H‑spiro[5‑nitroindoline‑3,4'‑pyrano[2,3‑c]pyrazole]‑5'‑carbonitrile
  参考文献：
  名称：

  FACILE MICROWAVE-ASSISTED ONE-POT SOLID PHASE SYNTHESIS OF SPIRO [3H-INDOLE-3,4'-PYRAZOLO[3,4-b] PYRIDINES]

  摘要：

  DOI：

  10.1515/hc.2003.9.4.415

文献信息

• Synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] and spiro[indoline-3,4′-pyrano[2,3-c]chromene] derivatives using silica-bonded ionic liquids as a recyclable catalyst in aqueous medium
  作者：Khodabakhsh Niknam、Abolhassan Piran、Zahra Karimi

  DOI：10.1007/s13738-015-0801-y

  日期：2016.5

  recyclable catalyst for the synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] via one-pot condensation reaction of isatin, activated methylene reagents, and 3-methyl-l-phenyl-5-pyrazolone in refluxing aqueous medium in good to high yields. Also, these silica-bonded ionic liquids were used as catalysts for the synthesis of spiro[indoline-3,4′-pyrano[2,3-c]chromene derivatives in refluxing aqueous medium

  摘要硅胶键合的离子液体用作可循环使用的催化剂，用于通过一锅的靛红，活化的亚甲基试剂和3-的缩合反应合成螺[吲哚啉-3,4'-吡喃并[2,3-c]吡唑]甲基-1-苯基-5-吡唑啉酮在回流的水性介质中的收率很高。而且，这些二氧化硅键合的离子液体也用作催化剂，用于在回流的水性介质中以高收率合成螺[吲哚啉-3,4'-吡喃并[2,3-c]苯甲基]衍生物。催化剂可以重复使用几次而无需任何其他处理。 图形概要二氧化硅键合的离子液体被用作可再循环的催化剂，用于合成螺[吲哚啉-3,4'-吡喃并[2,3-c]吡唑]和螺[吲哚啉-3,4'-吡喃并[2,3-] c]色烯，分别通过靛红，活化的亚甲基试剂和3-甲基-1-苯基-5-吡唑啉酮或4-羟基香豆素在回流的水性介质中一锅缩合反应，收率很高。
• A Green Efficient Synthesis of spiro[indoline-3,4′(1<i>H</i>‘)-pyrano [2,3-<i>c</i>]pyrazol]-2-one derivatives
  作者：Ying Liu、Dong Zhou、Zhongjiao Ren、Weiguo Cao、Jie Chen、Hongmei Deng、Qing Gu

  DOI：10.3184/030823409x416875

  日期：2009.3

  A highly efficient and green method has been described for the synthesis of spiropyranopyrazole-oxindole in water. The reaction was carried out at ambient temperature and the products were obtained in excellent isolated yields. The structure of the product (4e) was confirmed by X-ray diffraction analysis.

  本文介绍了一种在水中合成螺吡喃并吡唑-氧化吲哚的高效绿色方法。反应在常温下进行，产物的分离收率极高。X 射线衍射分析证实了产物 (4e) 的结构。
• Catalyst-free UV₃₆₅-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities
  作者：Arup Dutta、Noimur Rahman、John Elisa Kumar、Jintu Rabha、Tridip Phukan、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2020.1825741

  日期：2021.1.17

  A convenient and eco-friendly, one-pot synthetic protocol for pharmaceutically important pyran-based heterocyclic compounds is repeated herein. The reactions were carried out at room temperature in...

  本文重复了一种用于药学上重要的基于吡喃的杂环化合物的方便且环保的一锅合成方案。反应在室温下进行...
• Carbon–SO3H: a novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]
  作者：B. Maheshwar Rao、G. Niranjan Reddy、T. Vijaikumar Reddy、B.L.A. Prabhavathi Devi、R.B.N. Prasad、J.S. Yadav、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2013.02.089

  日期：2013.5

  A bioglycerol derived carbon-sulfonic acid is found to catalyze efficiently the three-component one-pot condensation of isatin, malononitrile, and 1,3-dicarbonyls to afford a wide range of spiro[4H-pyran-3,3′-oxindole]derivatives in good yields and selectivity. The use of a recyclable solid acid catalyst makes this method simple, convenient, and cost-effective.

  已发现生物甘油衍生的碳磺酸可有效催化伊斯丁，丙二腈和1,3-二羰基的三组分一锅缩合，从而提供广泛的螺[4H-吡喃-3,3'-羟吲哚]衍生物具有良好的产率和选择性。可循环使用的固体酸催化剂的使用使该方法简单，方便且具有成本效益。
• NaCl as a Novel and Green Catalyst for the Synthesis of Biodynamic Spiro Heterocycles in Water Under Sonication
  作者：Anshu Dandia、Anuj Kumar Jain、Dharmendra Singh Bhati

  DOI：10.1080/00397911.2010.515365

  日期：2011.10

  Abstract An efficient and novel green catalytic protocol for the synthesis of biologically important spirooxindole derivatives is developed in a one-pot, three-component approach involving substituted isatin, activated methylene reagent, and 3-methyl-1-phenyl-2-pyrazolin-5-one in water under sonication. This report describes the use of sodium chloride as a nonacidic and green catalyst for a variety

  摘要 一种用于合成具有生物学意义的螺羟吲哚衍生物的高效、新颖的绿色催化方案是通过一锅、三组分的方法开发的，包括取代的靛红、活化的亚甲基试剂和 3-methyl-1-phenyl-2-pyrazolin-5 - 一个在水中超声处理。本报告描述了氯化钠作为各种底物的非酸性和绿色催化剂的用途。这种方法的优点是环境友好、操作简单、产量高、易于处理以及产品不需要纯化。