5-chloro-3',7',7'-trimethyl-1'-phenyl-1',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(6'H)-dione | 1308671-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-3',7',7'-trimethyl-1'-phenyl-1',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(6'H)-dione
• 英文别名: 5-chloro-3',7',7'-trimethyl-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(1'H)-dione；5-chloro-3',7',7'-trimethyl-1'-phenylspiro[1H-indole-3,4'-8,9-dihydro-6H-pyrazolo[3,4-b]quinoline]-2,5'-dione
• CAS: 1308671-32-0
• 化学式: C₂₆H₂₃ClN₄O₂
• 分子量: 458.947
• InChiKey: ONOFWKPJNFMJBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 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 、 5-氯靛红 、 5,5-二甲基-1,3-环己二酮 在 papain from Carcica papaya 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以27%的产率得到5-chloro-3',7',7'-trimethyl-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：

  One-pot construction of spirooxindole backbone via biocatalytic domino reaction

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2017.06.031

文献信息

• 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.