ethyl 6′-amino-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate | 106536-40-7

• 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-3′-methyl-2-oxo-1′-phenyl-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carboxylate
• 英文别名: 6'-Amino-3'-methyl-2-oxo-1'-phenyl-spiro<2,3-dihydro-indol-3,4'-pyrano<2,3-c>pyrazol>-5'-carbonsaeure-ethylester；ethyl 6'-amino-3'-methyl-2-oxo-1'-phenylspiropyrazole>-5'-carboxylate；6'-amino-5'-ethoxycarbonyl-3'-methyl-1'-phenylspiropyrazol>-2-one；ethyl 6-amino-3-methyl-1-phenyl spiro[(3'H)-indol-3',4-4(H)pyrano(3,2-d)pyrazol]-(1'H)-2'-one-5-carboxylate；ethyl 6'-amino-3'-methyl-2-oxo-1'-phenyl-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate；ethyl 6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate；Ethyl 6'-amino-3'-methyl-2-oxo-1'-phenyl-1'h-spiro[indoline3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate；ethyl 6'-amino-3'-methyl-2-oxo-1'-phenylspiro[1H-indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carboxylate
• CAS: 106536-40-7
• 化学式: C₂₃H₂₀N₄O₄
• 分子量: 416.436
• InChiKey: YRSWWGKINAYPQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 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：

  ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate 、 依达拉奉 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到ethyl 6′-amino-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：

  Hafez, Ebtisam Abdel Aziz; Galil, Fathy M. Abdul; Sherif, Sherif M., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1375 - 1378

  摘要：

  DOI：

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• Nano-FGT: a green and sustainable catalyst for the synthesis of spirooxindoles in aqueous medium
  作者：Ramen Jamatia、Ajay Gupta、Amarta Kumar Pal

  DOI：10.1039/c5ra27552k

  日期：——

  glutathione grafted nano-organocatalyst (nano-FGT) was used as an efficient catalyst for the synthesis of spirooxindole derivatives. An aqueous medium, easy separation by an external magnet, efficient catalyst reusability, low catalyst loading, and column chromatography free separation of the product makes the present procedure green, sustainable and economically viable. The TON and TOF of the nanocatalyst

  谷胱甘肽接枝的纳米有机催化剂（nano-FGT）被用作合成螺恶英吲哚衍生物的有效催化剂。水性介质，易于被外部磁体分离，有效的催化剂可重复使用性，低的催化剂负载量以及产物的无柱色谱分离使本发明方法绿色，可持续且经济可行。纳米催化剂的TON和TOF分别达到850 000和56 667 min -1。
• Efficient One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by <scp>l</scp>-Proline in Aqueous Medium
  作者：Yuling Li、Hui Chen、Chunling Shi、Daqing Shi、Shunjun Ji

  DOI：10.1021/cc9001185

  日期：2010.3.8

  An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of l-proline is reported. This new protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, low cost, and convenient operation.

  据报道，在1-脯氨酸存在下，靛红，丙二腈（氰基乙酸酯）和1,3-二羰基化合物在水中的三组分反应可有效地一锅合成螺环吲哚衍生物。该新方案具有环境友好，产率高，反应时间短，成本低和操作方便的优点。
• 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。
• The Synthesis of Heterocycles from Indolin-2-one Derivatives and Active Methylene Reagents
  作者：Fathy F. Abdel-Latif、Ramadan A. Mekheimer、Mohamed M. Mashaly、Essam Kh. Ahmed

  DOI：10.1135/cccc19941235

  日期：——

  Investigation the synthesis of multifunctionalized heterocyclic spiro derivatives via the reaction of isatin, ethyl cyanoacetate and an other active methylene compound. It has been found that refluxing of an ethanolic piperidine solution of equimolar ratios of isatin (Ia), ethyl cyanoacetate (II) and barbituric acid (IIIa) or thiobarbituric acid (IIIb) afforded a solid product whose structure was assumed, in accordance with elemental analysis and IR and ¹H NMR spectra, to be VIIIa and VIIIb. Confirmation of the structures VIIIa and VIIIb follows from their preparation from compound IV, synthesized separately, and barbituric acids IIIa and IIIb in 1 : 1 molar ratio under the same reaction conditions.

  通过对异吲哚、乙基氰乙酸酯和另一种活性亚甲基化合物的反应合成多官能杂环螺环衍生物的研究。发现，在等摩尔比的异吲哚（Ia）、乙基氰乙酸酯（II）和巴比妥酸（IIIa）或硫巴比妥酸（IIIb）的乙醇哌嗪溶液中回流，得到了一种固体产物，根据元素分析、红外光谱和1H核磁共振谱，认为其结构为VIIIa和VIIIb。VIIIa和VIIIb的结构确认来自于它们在相同反应条件下，通过分别合成的化合物IV和巴比妥酸IIIa、IIIb按照1：1摩尔比制备而成。