ethyl 2'-amino-6'-methyl-2,5'-dioxo-5',6'-dihydrospiro[indoline-3,4'-pyrano[3,2-c]quinoline]-3'-carboxylate | 1163730-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 2'-amino-6'-methyl-2,5'-dioxo-5',6'-dihydrospiro[indoline-3,4'-pyrano[3,2-c]quinoline]-3'-carboxylate
• 英文别名: ethyl 2-amino-6-methyl-2',5-dioxo-5,6-dihydro-spiro[pyrano[3,2-c]quinoline-4,3'-indoline]-3-carboxylate；ethyl 2'-amino-6'-methyl-2,5'-dioxospiro[1H-indole-3,4'-pyrano[3,2-c]quinoline]-3'-carboxylate
• CAS: 1163730-40-2
• 化学式: C₂₃H₁₉N₃O₅
• 分子量: 417.421
• InChiKey: AQRBMBYCGRNTJG-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  683.9±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-1-甲基-2(1H)-喹啉酮 在 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate 作用下， 反应 0.6h， 生成 ethyl 2'-amino-6'-methyl-2,5'-dioxo-5',6'-dihydrospiro[indoline-3,4'-pyrano[3,2-c]quinoline]-3'-carboxylate
  参考文献：
  名称：

  离子液体介导的N-甲基喹诺酮绿色合成螺并吲哚及其抗细菌活性

  摘要：

  特定任务中涉及1-甲基喹啉-2,4（1 H，3 H）-二酮1，靛红2（a-e）和丙二腈/氰基乙酸酯3（a-b）缩合的三组分反应离子液体[DBU] [Ac]（1,8-二氮杂双环[5.4.0]-十一-7-en-8-乙酸乙酸盐）被描述为螺氧杂吲哚衍生物4（a–j）。这种方法无需柱色谱即可提供高收率的产品，并评估了所得化合物对革兰氏阳性和革兰氏阴性细菌（金黄色葡萄球菌， 大肠杆菌）的抗菌活性，蜡状芽孢杆菌，枯草芽孢杆菌，鼠伤寒沙门氏菌和肺炎克雷伯菌）。在所有化合物中，四种化合物，即4b，4e，4f，4g，4j与所用标准品相比，对所有菌株均表现出中等活性。

  DOI：

  10.1002/jhet.2821

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。
• Ultrasound-assisted the three-component synthesis of spiro[4H-pyrano[3,2-c]quinolin-4,3′-indoline]-2′,5(6H)-diones in water
  作者：Shaghyegh Gholizadeh、Koorosh Radmoghadam

  DOI：10.13005/ojc/290450

  日期：2013.12.30

  A simple and efficient synthesis of the titled spirooxindoles was accomplished via the three-component reaction between isatins, 4-hydroxy-2H-quinolin-2-one, and malononitrile or ethylcyanoacetate in aqueous medium under ultrasound irradiation.

  通过超声波辐照下的水相三组分反应，实现了标题螺环噁唑啉的简单高效合成，该反应涉及靛红、4-羟基-2H-喹啉-2-酮与丙二腈或乙基氰基乙酸酯的反应。
• El-Taweel; Elagamey; Elmougy, Sh.M., Egyptian Journal of Chemistry, 2011, vol. 54, # 6, p. 703 - 721
  作者：El-Taweel、Elagamey、Elmougy, Sh.M.

  DOI：——

  日期：——
• Ambient synthesis of spiro[4H-pyran-oxindole] derivatives under [BMIm]BF4 catalysis
  作者：Kurosh Rad-Moghadam、Leila Youseftabar-Miri

  DOI：10.1016/j.tet.2011.05.077

  日期：2011.8

  A simple and efficient one-pot approach for assembling some fused spiro[4H-pyran-oxindole] heterocycles by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds is reported. The combinatorial syntheses were achieved for the first time without applying extra activation energy at ambient temperature while making use of [BMIm]BF4 as an ionic liquid catalyst. Good functional group tolerance and broad scope of usable substrates are other prominent features of the present methodology. (C) 2011 Elsevier Ltd. All rights reserved.
• Ionic Liquid Mediated Green Synthesis of Spirooxindoles from <i>N</i> -methyl Quinolones and Their Anti Bacterial Activity
  作者：Raja S. Bhupathi、Bandi Madhu、Ch. Venkata Ramana Reddy、B. Rama Devi、P.K. Dubey

  DOI：10.1002/jhet.2821

  日期：2017.7

  quinoline‐2,4(1H,3H)‐dione 1, isatins 2(a–e), and malononitrile/cyanoacetic ester 3(a–b) in the task‐specific ionic liquid [DBU][Ac] (1,8‐diazabicyclo[5.4.0]‐undec‐7‐en‐8‐ium acetate) leading to the spirooxindole derivatives 4(a–j) is described. This approach is affords the products in high yields without use of column chromatography and resulting compounds were evaluated for antibacterial activity against both

  特定任务中涉及1-甲基喹啉-2,4（1 H，3 H）-二酮1，靛红2（a-e）和丙二腈/氰基乙酸酯3（a-b）缩合的三组分反应离子液体[DBU] [Ac]（1,8-二氮杂双环[5.4.0]-十一-7-en-8-乙酸乙酸盐）被描述为螺氧杂吲哚衍生物4（a–j）。这种方法无需柱色谱即可提供高收率的产品，并评估了所得化合物对革兰氏阳性和革兰氏阴性细菌（金黄色葡萄球菌， 大肠杆菌）的抗菌活性，蜡状芽孢杆菌，枯草芽孢杆菌，鼠伤寒沙门氏菌和肺炎克雷伯菌）。在所有化合物中，四种化合物，即4b，4e，4f，4g，4j与所用标准品相比，对所有菌株均表现出中等活性。