3',7',7'-trimethyl-5-nitro-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(1'H)-dione | 1308671-33-1

• 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',7',7'-trimethyl-5-nitro-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(1'H)-dione
• 英文别名: 3',7',7'-trimethyl-5-nitro-1'-phenylspiro[1H-indole-3,4'-8,9-dihydro-6H-pyrazolo[3,4-b]quinoline]-2,5'-dione
• CAS: 1308671-33-1
• 化学式: C₂₆H₂₃N₅O₄
• 分子量: 469.5
• InChiKey: BMERBESIIQKISA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 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：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氨基巴豆腈 、 5-硝基靛红 、 5,5-二甲基-1,3-环己二酮 、 苯肼 在 camphor-10-sulfonic acid 作用下， 以 水 为溶剂， 反应 3.0h， 以94%的产率得到3',7',7'-trimethyl-5-nitro-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(1'H)-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.03.020

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.