ethyl 6′-amino-5-chloro-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate | 900877-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 6′-amino-5-chloro-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate
• 英文别名: ethyl 6'-amino-5-chloro-3'-methyl-2-oxo-1'-phenyl-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate；ethyl 6'-amino-5-chloro-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate；ethyl 6'-amino-5-chloro-3'-methyl-1'-phenylspiro[indole-3,4'-pyrano(3',2'-d)pyrazole]-2-one-5'-carboxylate；Ethyl-6'-amino-5-chloro-3'-methyl-2-oxo-1'-phenyl-1'h-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate；ethyl 6'-amino-5-chloro-3'-methyl-2-oxo-1'-phenylspiro[1H-indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate
• CAS: 900877-65-8
• 化学式: C₂₃H₁₉ClN₄O₄
• 分子量: 450.881
• InChiKey: BONBAPGFUAEHCC-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(Solv: ethanol (64-17-5))
• 沸点：
  685.0±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氯靛红 、 氰乙酸乙酯 、 依达拉奉 在 ZnS nanoparticles 作用下， 以 水 为溶剂， 反应 0.25h， 以93%的产率得到ethyl 6′-amino-5-chloro-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate
  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

• 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。
• 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。
• A Facile Synthesis of Some Spirooxoindole Derivatives via One-Pot Three-Component Reactions
  作者：Ghada E. Badri、Fatma E.M. El-Baih、Hassan M. Al-Hazimi

  DOI：10.14233/ajchem.2013.14270

  日期：——

  Tetrahydrospiro[chromene-4,3-indole]-2-ones (5a-c) and spiro[indole-3,4-pyrano(3,2-d)pyrazole]-2-ones (6a-b) have been synthesized based on the one-pot three-component cyclocondensation reaction of 5-(un)substituted isatins (1a-c) with ethyl cyanoacetate (2) and 5,5-dimethylcyclohexane-1,3-dione (3) or 5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one (4) in absolute ethanol containing a catalytic amount of Et3N carried out under both conventional heating and environmentally benign procedures. The structures of the resulting compounds were confirmed by spectral IR, 1H NMR, 13C NMR, 2D NMR [1H-1H COSY, 1H-13C COSY (HETCOR)] and electrospray ionization tandem mass [(±) ESI-MS/MS]} analysis.

  合成了四氢螺[色烯-4,3-吲哚]-2-酮(5a-c)和螺[吲哚-3,4-吡喃(3,2-d)吡唑]-2-酮(6a-b)基于5-(未)取代靛红(1a-c)与氰基乙酸乙酯(2)和5,5-二甲基环己烷-1,3-二酮(3)或5-甲基-的一锅三组分环缩合反应2-苯基-2,4-二氢-吡唑-3-酮(4)在含有催化量的Et3N的无水乙醇中在常规加热和环境友好的程序下进行。所得化合物的结构通过光谱IR、1H NMR、13C NMR、2D NMR [1H-1H COSY、1H-13C COSY (HETCOR)]和电喷雾电离串联质量[(±) ESI-MS/MS]确认} 分析。
• Ultrasound promoted green synthesis of spiro[pyrano[2,3-c]pyrazoles] as antioxidant agents
  作者：Anshu Dandia、Deepti Saini、Sumit Bhaskaran、Dinesh Kumar Saini

  DOI：10.1007/s00044-013-0671-8

  日期：2014.2

  Ultrasound promoted, cerium ammonium nitrate catalyzed sustainable synthesis of spiro[indoline3,4'-pyrano[2,3-c]pyrazole] derivatives (4a-l) is reported herein. The synthesized compounds were screened for their antioxidant activities as free radical scavenging effect on diphenylpicryl hydrazine (DPPH center dot), 2,2'-azino-bis(3-ethylbenzthiazoline- 6-sulphonic acid) (ABTS(center dot+)) and nitric oxide (NO) radicals. The screened compounds showed potent scavenging activities against DPPH center dot, ABTS(center dot+) and NO radicals. In order to further extend on studies and to obtain a deep insight into structure activity relationship of this class of compounds, we designed N-substitution of indole moiety with the aim to study its antioxidant potential.
• 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。