ethyl 2-amino-5′-nitro-7,7-dimethyl-2′,5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3′-indoline]-3-carboxylate | 1321787-69-2

• 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: ethyl 2-amino-5′-nitro-7,7-dimethyl-2′,5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3′-indoline]-3-carboxylate
• 英文别名: ethyl 2-amino-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carboxylate；ethyl 2-amino-7,7-dimethyl-5'-nitro-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carboxylate；ethyl 2-amino-7,7-dimethyl-5-nitro-2',5-dioxo-5, 6,7, 8-tetrahydrospiro[chromene-4,3-indoline]-3-carboxylate；ethyl 2'-amino-7',7'-dimethyl-5-nitro-2,5'-dioxospiro[1H-indole-3,4'-6,8-dihydrochromene]-3'-carboxylate
• CAS: 1321787-69-2
• 化学式: C₂₁H₂₁N₃O₇
• 分子量: 427.414
• InChiKey: OICNHCNWBNZWBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-硝基靛红 、 5,5-二甲基-1,3-环己二酮 、 氰乙酸乙酯 在 sodium chloride 作用下， 以 水 为溶剂， 反应 0.33h， 以92%的产率得到ethyl 2-amino-5′-nitro-7,7-dimethyl-2′,5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3′-indoline]-3-carboxylate
  参考文献：
  名称：

  NaCl 作为一种新型绿色催化剂，用于在水中超声合成生物动力螺杂环

  摘要：

  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。

  DOI：

  10.1080/00397911.2010.515365

文献信息

• Oxalic acid dihydrate: proline as a new recyclable designer solvent: a sustainable, green avenue for the synthesis of spirooxindole
  作者：Dattatray R. Chandam、Abhijeet G. Mulik、Dayanand R. Patil、Madhukar B. Deshmukh

  DOI：10.1007/s11164-015-2093-3

  日期：2016.2

  encouraged to explore oxalic acid dihydrate: proline low transition temperature mixture as a new designer solvent for the said synthesis at room temperature. It has been successfully applied for the three component reaction of isatin, malononitrile or ethyl cyanoacetate and 1,3–dicarbonyl compounds for the first time. Moderate to good yield of the products, shorter reaction time, energy efficiency, chromatography-free

  摘要 为开发具有巨大生物活性的螺氧基吲哚衍生物的环保，可持续协议的要求鼓励了探索草酸二水合物：脯氨酸低转变温度混合物作为在室温下所述合成的新型设计溶剂。它已成功地首次用于靛红，丙二腈或氰基乙酸乙酯与1,3-二羰基化合物的三组分反应。该产品具有中等至良好的收率，较短的反应时间，能源效率，无色谱纯化工艺，可回收性和高原子经济性是该协议的诱人特性，将在多组分，面向多样性的合成中得到应用。 图形概要
• A Simple and One-pot Synthesis of Tetrahydrobenzo[b]pyrans and Spirooxindoles Catalyzed by H-Fe3O4@DA-SO3H as an Efficient, Light and Reusable Nanocatalyst
  作者：Marzie Sadat Mirhosseyni、Firouzeh Nemati、Ali Elhampour

  DOI：10.2174/1386207321666180817142658

  日期：2018.11.15

  chemistry is using inexpensive reagents and catalysts to design green route for synthesis of organic compounds. Recently magnetic nanoparticles have provided a considerable merits. In this study, hollow Fe3O4@Dopamine-SO3H has been successfully applied for the green synthesis of tetrahydrobenzo[b]pyrans and spirooxindoles via one-pot multi-component reaction. MATERIALS AND METHODS Chemical reagents were purchased

  目的和目标绿色化学的原理之一是使用廉价的试剂和催化剂来设计合成有机化合物的绿色途径。最近，磁性纳米颗粒已经提供了相当多的优点。在这项研究中，空心Fe3O4 @ Dopamine-SO3H已通过一锅多组分反应成功地用于绿色合成四氢苯并[b]吡喃类和螺硫醇。材料与方法化学试剂购自Merck和Aldrich。使用Electrothermal 9100测定熔点。分别用Shimadzu 8400光谱仪和Bruker光谱仪记录傅立叶变换红外光谱和NMR光谱。结果选择了苯甲醛，丙二腈和二甲酮之间的反应作为合成四氢苯并[b]吡喃的模型。所得结果表明，最佳催化剂量为0.01g，反应在70℃无溶剂条件下进行。结果表明吸电子和给电子取代基在反应中均具有可接受的产率。此后，通过靛红衍生物，丙二腈或氰基乙酸乙酯与1，3-环二酮的三组分反应，对一锅合成螺并吲哚衍生物进行了评价。最佳条件是在回流条件下使用H2O的催化剂为0
• A New Reaction of Isatin, Cyclic 1,3-Diketone, and 2-Cyanoacetamide: A Four-Component Synthesis of Spirooxindoles
  作者：Ramin Ghahremanzadeh、Ghaffar Hosseini、Roya Akbarzadeh、Ayoob Bazgir

  DOI：10.1002/jhet.1010

  日期：2013.3

  A novel reaction of isatins, 2‐cyanoacetamide, and cyclic 1,3‐diketones in ethanol was reported. The reaction gave the unexpected spirooxindole ethyl carboxylates in excellent yields and the spirooxindole carboxamide was not observed.

  据报道，靛红，2-氰基乙酰胺和环状1,3-二酮在乙醇中发生了新的反应。该反应以优异的产率得到了意想不到的螺并吲哚羧酸乙酯，未观察到螺并吲哚羧酰胺。
• Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium via Knoevenagel condensation followed by Michael addition
  作者：Anshu Dandia、Vijay Parewa、Anuj Kumar Jain、Kuldeep S. Rathore

  DOI：10.1039/c1gc15244k

  日期：——

  An environmentally friendly, one-pot, three-component ZnS nanoparticle-mediated synthesis of biologically important spirooxindole derivatives in water under ultrasonic irradiation is described herein. ZnS nanoparticles were synthesized by aqueous chemical method. The advantages of this method lies in its simplicity, cost effectiveness, environment friendliness, easier scaling up for large scale synthesis without using high pressure, temperature and toxic chemicals. Greenness of the process was well instituted as water was exploited both as reaction media as well as medium for synthesis of catalyst (ZnS nanoparticles). The particle size was determined by transmission electron microscopy (TEM) and XRD. Compared with other methods for synthesis of spirooxindole derivatives, satisfactory results were obtained with high yields, short reaction time, with simple experimental procedure. After reaction course, the ZnS NPs can be recycled and reused without any apparent loss of activity.

  本文介绍了一种在超声波辐照下，以 ZnS 纳米粒子为介导，在水中合成具有重要生物活性的螺吲哚衍生物的环保型一锅三组份合成方法。ZnS 纳米粒子采用水化学方法合成。这种方法的优点在于简单、成本效益高、环境友好，而且无需使用高压、高温和有毒化学品，更容易进行大规模合成。由于水既可用作反应介质，也可用作合成催化剂（ZnS 纳米粒子）的介质，因此该工艺绿色环保。粒度由透射电子显微镜（TEM）和 XRD 确定。与其他合成螺吲哚衍生物的方法相比，该方法产率高、反应时间短、实验过程简单，取得了令人满意的结果。反应过程结束后，ZnS NPs 可回收再利用，且没有明显的活性损失。
• Synthesis of Zr-MOF/rGO-nanocomposites used for spirooxindole scaffolds derivatives
  作者：Gyanendra Kumar、Arup Dutta、Munmee Goswami、Bachan Meena、Sreehari Parasuboyina、Rishanlang Nongkhlaw、Dhanraj T. Masram

  DOI：10.1016/j.molstruc.2023.135653

  日期：2023.9

  A highly resourceful synthetic strategy has been developed for the production of spirooxindole derivatives employing Zr-MOF/rGO nanocomposites as a heterogeneous catalyst in aqueous ethanol environments. This protocol involves a three-component one-pot reaction comprising isatin, malononitrile, or ethyl cyanoacetate as well as several 1,3-dicarbonyl compounds at room temperature. In addition to achieving

  已经开发出一种资源丰富的合成策略，用于在含水乙醇环境中使用 Zr-MOF/rGO 纳米复合材料作为多相催化剂生产螺氧吲哚衍生物。该协议涉及三组分一锅反应，包括靛红、丙二腈或氰基乙酸乙酯以及室温下的几种 1,3-二羰基化合物。除了在反应混合物中获得合成有机产物外，还可以通过离心方便地收集产生的催化剂。这种方法有几个显着的优点，包括使用绿色溶剂、反应时间短、操作简单、反应条件简单和产品收率高。此外，所得 Zr-MOF/rGO 纳米催化剂具有稳定性好、活性高、