2-amino-5',7,7,7'-tetramethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile | 1321787-76-1

• 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',7,7,7'-tetramethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile
• 英文别名: 2'-amino-5,7,7',7'-tetramethyl-2,5'-dioxospiro[1H-indole-3,4'-6,8-dihydrochromene]-3'-carbonitrile
• CAS: 1321787-76-1
• 化学式: C₂₁H₂₁N₃O₃
• 分子量: 363.416
• InChiKey: MINDTEQOMCPXHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5,7-二甲基靛红 、 5,5-二甲基-1,3-环己二酮 、 丙二腈 在 ZnS nanoparticles 作用下， 以 水 为溶剂， 反应 0.2h， 以96%的产率得到2-amino-5',7,7,7'-tetramethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile
  参考文献：
  名称：

  Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium via Knoevenagel condensation followed by Michael addition

  摘要：

  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。

  DOI：

  10.1039/c1gc15244k

文献信息

• One-Pot Three-Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water
  作者：Guo-Dong Wang、Xiao-Nan Zhang、Zhan-Hui Zhang

  DOI：10.1002/jhet.994

  日期：2013.1

  convenient, and multicomponent strategy for synthesis of spirooxindole derivatives has been developed. This strategy provides a rapid access to construct a diversity‐oriented library of spirooxindoles by using three simple and readily available isatin, malononitrile or cyanoacetic ester, and 1,3‐dicarbonyl compound catalyzed by hexamethylenetetramine in water.

  已经开发出一种简单，方便和多组分合成螺环吲哚衍生物的策略。通过使用三种简单易得的Isatin，丙二腈或氰基乙酸酯以及六亚甲基四胺在水中催化的1,3-二羰基化合物，该策略可快速构建以螺菌毒素为导向的多样性文库。
• 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。
• 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。
• Solvent-free multicomponent assembling of isatins, malononitrile, and dimedone: fast and efficient way to functionalized spirooxindole system
  作者：Michail N. Elinson、Fedor V. Ryzhkov、Tatiana A. Zaimovskaya、Mikhail P. Egorov

  DOI：10.1007/s00706-015-1617-2

  日期：2016.4

  Solvent-free sodium acetate catalyzed multicomponent reaction of isatins, malononitrile, and dimedone initiated by grinding in mortar results in the fast and efficient formation of substituted spirooxindoles in 90-99 % yields. The developed solvent-free fast multicomponent approach to the substituted spirooxindoles-the pharmacologically perspective substances with spasmolytic, diuretic, anticoagulant, anticancer, and antianaphylactic activities-is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast efficient and environmentally benign solvent-free synthetic concept for multicomponent reactions strategy.
• Synthesis of spiropyran derivatives over 1-(carboxymethyl) pyridinium iodide as nanostructured pyridinium salt under aqueous media
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Rasoul Salehi-Moratab、Ehsan Noroozizadeh

  DOI：10.1139/cjc-2016-0374

  日期：2017.2

  In this work, acetic acid functionalized pyridinium salt, namely 1-(carboxymethyl)pyridinium iodide [cmpy]I}, has been applied as reusable nanostructured catalyst for green, simple and efficient preparation of spiropyrans by the one-pot domino Knoevenagel–Michael–cyclization reaction of isatin derivatives or acenaphthenquinone, with malononitrile, and 1,3-dicarbonyl compounds under aqueous media. Moreover, ¹H and ¹³C NMR, mass, CHN analysis, Fourier transform infrared spectroscopy (FTIR), scanning electron microscope (SEM), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), X-ray diffraction analysis (XRD), and calculation of crystallite size and interplaner distance of the catalyst have been studied.

  在这项工作中，乙酸功能化吡啶盐，即1-(羧甲基)吡啶碘化物 [cmpy]I}，已被应用为可重复使用的纳米结构催化剂，用于通过一锅法在水介质下简单高效地制备螺环吡喃。这种螺环吡喃是通过吲哚酮衍生物或苯并蒽醌与马来酰亚胺和1,3-二羰基化合物的Knoevenagel-Michael-环化反应实现的。此外，研究了 ¹H 和 ¹³C 核磁共振、质谱、元素分析、傅立叶变换红外光谱（FTIR）、扫描电子显微镜（SEM）、热重分析（TGA）、差热重（DTG）、X射线衍射分析（XRD）以及计算了催化剂的晶粒尺寸和层间距离。