6'‑amino‑3'‑methyl‑2‑oxo-1'‑phenyl‑1'H‑spiro[5‑chloroindoline‑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‑chloroindoline‑3,4'‑pyrano[2,3‑c]pyrazole]‑5'‑carbonitrile
• 英文别名: 6’-amino- 5-chloro-3’-methyl-2-oxo-1’phenyl-1’H-spiro[indoline-3,4’-pyrano[2,3-c]pyrazole]-5’carbonitrile；6'-amino-5-chloro-3'-methyl-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-chloroindoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-5'-cyano-3'-methyl-1'-phenyl-5-chlorospiro[indoline-3,4'(1'H)-pyrano[2,3-c]pyrazole]-2-one；6'-amino-5-chloro-5'-cyano-3'-methyl-1'-phenylspiro[indoline-3,4'(1H')-pyrano[2,3-c]pyrazol]-2-one；6'-amino-5-chloro-3'-methyl-2-oxo-1'-phenyl-1,2-dihydro-1'H-spiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-5-chloro-3'-methyl-2-oxo-1'-phenylspiro[1H-indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 化学式: C₂₁H₁₄ClN₅O₂
• 分子量: 403.827
• InChiKey: WLUMADZMKYUYQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 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：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯靛红 在 aluminum oxide 作用下， 反应 0.09h， 生成 6'‑amino‑3'‑methyl‑2‑oxo-1'‑phenyl‑1'H‑spiro[5‑chloroindoline‑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

• 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。
• Na2EDTA: an efficient, green and reusable catalyst for the synthesis of biologically important spirooxindoles, spiroacenaphthylenes and spiro-2-amino-4H-pyrans under solvent-free conditions
  作者：Tayebeh Jazinizadeh、Malek Taher Maghsoodlou、Reza Heydari、Afshin Yazdani-Elah-Abadi

  DOI：10.1007/s13738-017-1148-3

  日期：2017.10

  For the first time, the organic salt Na2EDTA was used as a catalyst for an effective and facile preparation of spiro-4H-pyrans via single-pot three-component condensation of isatin/acenaphthoquinone/ninhydrin, malononitrile, and CH-acids through Knoevenagel–Michael–annulation sequence. This new protocol employing Na2EDTA, which is a green, recyclable, and inexpensive catalyst, offers advantages such

  第一次，将有机盐Na 2 EDTA用作催化剂，通过Isatin / ac萘醌/茚三酮，丙二腈和CH-酸的单锅三组分缩合反应，有效而便捷地制备spiro-4 H -pyrans通过Knoevenagel–Michael–环形序列。这项采用Na 2 EDTA的新方案是一种绿色，可回收且廉价的催化剂，具有无溶剂，高效反应条件，反应时间短（10-15分钟），后处理容易，收率高等优点。比其他环境合成方法更经济。
• Bovine serum albumin catalyzed one-pot, three-component synthesis of dihydropyrano[2,3-c]pyrazole derivatives in aqueous ethanol
  作者：Kiran S. Dalal、Yogesh A. Tayade、Yogesh B. Wagh、Darshak R. Trivedi、Dipak S. Dalal、Bhushan L. Chaudhari

  DOI：10.1039/c5ra13014j

  日期：——

  (BSA) catalyzed synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one pot, three component reaction of an aldehyde/ketone/isatin, malononitrile and 3-methyl-1H-pyrazol-5-(4H)-one in H2O–EtOH (7 : 3) at ambient temperature was developed in this work. The catalyst was found to work efficiently for aldehydes, ketones and isatins to give the corresponding dihydropyrano[2,3-c]pyrazole and spiro[indoline-3

  牛血清白蛋白（BSA）通过一锅，醛/酮/ Isatin，丙二腈和3-甲基-1 H-吡唑-5-（4）的三组分反应催化合成二氢吡喃并[2,3- c ]吡唑衍生物在这项工作中，在环境温度下在H 2 O–EtOH（7：3）中形成了H）-1。发现该催化剂可有效地用于醛，酮和靛红，得到相应的二氢吡喃并[2,3- c ]吡唑和螺[吲哚啉-3,4'-吡喃并[2,3- c][吡唑]衍生物的收率很高。BSA对各种醛，芳族/脂肪族酮和取代的isatins表现出广泛的催化混杂性。使用对环境无害的方案，催化剂的可重复使用性，避免使用有害溶剂，优异的收率，易于加工且不会形成副产物，使得BSA成为进一步用作生物催化剂的有吸引力的候选者。
• 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。