6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile | 74647-55-5

• 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-4'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 英文别名: 6'‑amino‑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[indoline-3,4’-pyrano[2,3-c]pyrazole]-5’- carbonitrile；6'-amino-5'-cyano-3'-methyl-1'-phenylspiropyrazole>-2-one；spiropyrazole)>；6-amino-3-methyl-1-phenyl spiro[(3'H)-indol-3',4-4(H)pyrano(3,2-d)pyrazol]-(1'H)-2'-one-5-carbonitrile；6'-amino-3'-methyl-2-oxo-1'-(p-tolyl)-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-3'-methyl-2-oxo-1'-phenyl-1,2-dihydro-1'H-spiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-3'-methyl-2-oxo-1'-phenylspiro[1H-indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• CAS: 74647-55-5
• 化学式: C₂₁H₁₅N₅O₂
• 分子量: 369.382
• InChiKey: DQOPBBDEGXOTAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 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

• 作为反应物：
  描述：

  6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile 在 溶剂黄146 作用下， 以 苯 为溶剂， 反应 7.0h， 生成 1-diethoxymethyl-6'-diethylaminomethylideneamino-3'-methyl-2-oxo-1'-phenyl-1,2-dihydro-1'H-spiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
  参考文献：
  名称：

  New method for functionalization of 6′-amino-3′-methyl-2-oxo-1′-phenyl-1,2-dihydro-1′H-spiro[indole-3,4′-pyrano-[2,3-c]pyrazole]-5′-carbonitrile

  摘要：

  DOI：

  10.1134/s1070428006100320
• 作为产物：
  描述：

  靛红 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
  参考文献：
  名称：

  取代的吡喃并[2,3- c ]吡唑类化合物的生态友好合成及生物学评价

  摘要：

  通过在完全非催化条件下在乙醇水溶液中的多组分一锅法开发了一种环保的绿色方法，用于合成取代的吡喃并[2,3- c ]吡唑。评价合成的化合物的抗菌，抗炎和细胞毒性活性。

  DOI：

  10.1016/j.bmcl.2012.06.055

文献信息

• Synthesis and characterization of acetic acid functionalized poly (4-vinylpyridinium) salt as new catalyst for the synthesis of spiropyran derivatives and their biological activity
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Ehsan Noroozizadeh、Mahmoud Zarei、Roya Karamian、Mostafa Asadbegy

  DOI：10.1016/j.molcata.2016.10.011

  日期：2016.12

  Abstract Acetic acid functionalized poly(4-vinylpyridinium) bromide (APVPB), as a new and heterogeneous catalyst, was designed and successfully tested on the synthesis of 2-aminospiro[indoline-3,4ʹpyran]-2-one and spiro[indeno[1,2-b]quinoxaline-11,4-pyran]-2ʹ-amine derivatives. Also, infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), scanning

  摘要 醋酸功能化聚（4-乙烯基吡啶）溴化物（APVPB）作为一种新型的非均相催化剂，设计并成功用于合成2-氨基螺[indoline-3,4ʹpyran]-2-one和螺[indeno[ 1,2-b]quinoxaline-11,4-pyran]-2ʹ-胺衍生物。此外，红外光谱（FT-IR）、热重分析（TGA）、差热重重（DTG）、扫描电子显微镜（SEM）、X射线衍射分析（XRD）和能量色散X射线分析（EDX）该催化剂已在所提出的工作中进行了研究。将制备的螺吡喃溶解在DMSO中，通过DPPH自由基清除试验和对尖孢镰刀菌的抗真菌活性进行抗氧化活性筛选。结果表明，合成的螺吡喃具有很强的抗氧化活性（IC50；0.161 ± 0.009 to 1. 509 ± 0.007 mg/ml）和对尖孢镰刀菌的良好抑制活性（在 500 ppm 浓度下为 65.8 ± 1.4% 至 88.3 ± 2.2%，在 1000
• Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans
  作者：Hamid Reza Safaei、Mohsen Shekouhy、Sudabeh Rahmanpur、Athar Shirinfeshan

  DOI：10.1039/c2gc35135h

  日期：——

  Glycerol is applied as a green, biodegradable and reusable promoting medium for one-pot three component synthesis of 4H-pyrans under catalyst-free conditions. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatine derivatives, acenaphthenequinone and ninehydrine are condensed with carbonyl compounds possessing a reactive α-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The reaction medium could be recycled and reused several times without any loss of efficiency.

  甘油作为绿色、生物可降解且可重复利用的促进介质，在无催化剂条件下用于一锅法三组分合成4H-吡喃。广泛的一系列底物，包括芳香和杂环醛、吲哚醌衍生物、苊醌和九氢吲哚，与具有活性α-亚甲基的羰基化合物及烷基丙二酸酯进行缩合反应。所有反应均在短时间内完成，产物收率良好至优异。反应介质可回收并重复使用多次，效率无任何损失。
• 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。