3'-methyl-1'-phenyl-1',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(6'H)-dione | 1231744-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3'-methyl-1'-phenyl-1',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(6'H)-dione
• 英文别名: 3'-methyl-1'-phenyl-6',7',8',9'-tetrahydrospiro-[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(1'H)-dione；3'-methyl-1'-phenylspiro[1H-indole-3,4'-6,7,8,9-tetrahydropyrazolo[3,4-b]quinoline]-2,5'-dione
• CAS: 1231744-28-7
• 化学式: C₂₄H₂₀N₄O₂
• 分子量: 396.448
• InChiKey: OJRWYYDGMJLZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 靛红 、 1,3-环己二酮 在 对甲苯磺酸 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到3'-methyl-1'-phenyl-1',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(6'H)-dione
  参考文献：
  名称：

  通过5-氨基吡唑，靛红和环状β-二酮的三组分反应有效合成吡唑并[3,4- b ]吡啶-4-螺吲哚酮

  摘要：

  新型吡唑并吡啶-螺并吲哚满酮是通过5-氨基吡唑，靛红和环状β-二酮在水性介质中的三组分反应制备的，并通过p -TSA催化。该协议提供了一个简单的一步程序，具有易于处理，反应条件温和且对环境无害的优点。

  DOI：

  10.1016/j.tetlet.2011.03.067

文献信息

• Efficient One-Pot Synthesis of Novel Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium
  作者：Hui Chen、Daqing Shi

  DOI：10.1021/cc100056p

  日期：2010.7.12

  A novel and efficient one-pot synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]dione, spiro[furo[3,4-e]pyrazolo[3,4-b]pyridine-4,3'-indoline]dione, and spiro[indeno[2,1-e]pyrazolo[3,4-b]pyridine-4,3'-indoline]dione derivatives via three-component reaction of isatin, 5-amino-3-methylpyrazole, and 1,3-dicarbonyl compounds in aqueous medium is described. The advantages of this method include

  螺[吲哚啉-3,4'-吡唑并[3,4-b]喹啉]二酮，螺[呋喃[3,4-e]吡唑并[3,4-b]吡啶- 4,3'-二氢吲哚]二酮和螺[茚并[2,1-e]吡唑并[3,4-b]吡啶-4,3'-二氢吲哚]二酮衍生物是通过Isatin，5-amino的三组分反应描述了在水性介质中的-3-甲基吡唑和1，3-二羰基化合物。该方法的优点包括高效，温和的反应条件，方便的操作以及对环境有益的条件。
• New four-component reactions in water: a convergent approach to the metal-free synthesis of spiro[indoline/acenaphthylene-3,4′-pyrazolo[3,4-b]pyridine derivatives
  作者：Kamaraj Balamurugan、Subbu Perumal、J. Carlos Menéndez

  DOI：10.1016/j.tet.2011.03.020

  日期：2011.5

  New four-component domino reactions are described that allow the one-pot synthesis of spiro[indoline/acenaphthylene-3,4'-pyrazolo[3,4-b]pyridine derivatives from the reaction of phenylhydrazine, 3-aminocrotononitrile, isatin/acenaphthylene-1,2-dione, and cyclic 1,3-dicarbonyl compounds, including cyclohexane-1,3-diones, barbituric acid, and 2-thioxodihydropyrimidine-4,6(1H,5H)-dione, in the presence of (+/-)-camphor-10-sulfonic acid (CSA). These processes take place in water and involve the generation of two rings and five new bonds (two C-C, two C-N and one C = N) in a single synthetic operation, with expedient work-up and diminished waste generation due to the absence of extraction and purification steps. (C) 2011 Elsevier Ltd. All rights reserved.
• One-pot construction of spirooxindole backbone via biocatalytic domino reaction
  作者：Yi-Ru Liang、Yu-Jing Hu、Xue-Han Zhou、Qi Wu、Xian-Fu Lin

  DOI：10.1016/j.tetlet.2017.06.031

  日期：2017.7

  A simple and environmentally friendly method to synthesize spiropyrazolo[3,4-b]pyridines derivatives starting from isatin, cyclic-1,3-diketone and 3-methyl-5-aminopyrazole was developed. With the optimized conditions for enzymes, solvents, enzyme loading and reaction time in hand, 9 compounds were obtained in acceptable yields. Moreover, the investigation in fluorescent properties of these products showed their potential application in the field of new fluorescent material. (C) 2017 Elsevier Ltd. All rights reserved.