spiro[3,4']-1,3-dihydro-2H-indol-2-one-4',6',7',8'-tetrahydro-2',5'(1'H,3'H)quinazolinedione | 1235515-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: spiro[3,4']-1,3-dihydro-2H-indol-2-one-4',6',7',8'-tetrahydro-2',5'(1'H,3'H)quinazolinedione
• 英文别名: spiro[4.3']oxindole-3,4,7,8-tetrahydroquinazoline-2,5-(1H,6H)-dione；spiro[1H-indole-3,4'-3,6,7,8-tetrahydro-1H-quinazoline]-2,2',5'-trione
• CAS: 1235515-88-4
• 化学式: C₁₅H₁₃N₃O₃
• 分子量: 283.287
• InChiKey: ZIEJZHDXDDPXQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 、 1,3-环己二酮 、 尿素 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以91%的产率得到spiro[3,4']-1,3-dihydro-2H-indol-2-one-4',6',7',8'-tetrahydro-2',5'(1'H,3'H)quinazolinedione
  参考文献：
  名称：

  PTSA催化新型羟吲哚衍生物的新型一锅法合成

  摘要：

  摘要 在乙腈中，在催化量的对甲苯磺酸存在下，通过尿素、靛红和1,3-二羰基化合物的三组分反应，一锅法合成螺环吲哚。

  DOI：

  10.1080/00397911.2010.515364

文献信息

• TiO₂–SiO₂ nanocomposite as a highly efficient catalyst for the solvent-free cyclocondensation reaction of isatins, cyclohexanones, and urea
  作者：Simin Janitabar-Darzi、Shahrzad Abdolmohammadi

  DOI：10.1515/znb-2019-0059

  日期：2019.8.27

  A TiO₂–SiO₂ nanocomposite catalyzes the one-pot cyclocondensation reaction of 1H-indole-2,3-diones (isatins), 1,3-cyclohexanediones, and urea at T = 70°C under solvent-free conditions with high efficiency. The present method affords the corresponding spiro products in high yields and short reaction time. The unique features of the TiO₂–SiO₂ nanocomposite are high catalytic activity, ease of preparation, non-toxicity, low loading, and recyclability.

  一种TiO₂–SiO₂纳米复合催化剂在无溶剂条件下，以高效率催化1H-吲哚-2,3-二酮（异酮）、1,3-环己二酮和尿素的一锅式环合反应，反应温度为T = 70°C。该方法可以高产率地生成相应的螺环产物，并且反应时间短。TiO₂–SiO₂纳米复合催化剂的独特特点是具有高催化活性、易于制备、无毒、负载量低和可重复使用。

• A Novel Biginelli-Like Reaction: An Efficient One-pot Synthesis of Spiro[oxindole-quinazoline/pyrimidine]ones
  作者：Hassan Kefayati、Kurosh Rad-Moghadam、Masoumeh Zamani、Sanaz Hosseyni

  DOI：10.2174/157017810791130577

  日期：2010.6.1

  Some new spiro[oxindole-quinazoline/pyrimidine]ones were synthesized via a novel three-component Biginelli-like reaction between isatin, cyclic or acyclic 1,3-dicarbonyl compounds, and urea, N-methyl urea or thiourea in one pot and good yields.

  通过靛红、环状或非环状 1,3-二羰基化合物与尿素、N-甲基尿素或硫脲在一锅中的新型三组分类 Biginelli 反应合成了一些新的螺[羟吲哚-喹唑啉/嘧啶]酮类化合物。产量。
• A novel one-pot synthesis of spirooxindole derivatives catalyzed by nano ZnO
  作者：B. Baghernejad、M. Khorshidi

  DOI：10.4314/bcse.v27i2.17

  日期：——

  Nano zinc oxide was explored as a heterogeneous and reusable catalyst for the one-pot synthesis of spirooxindoles via three-component reaction between urea, isatin, and 1,3-dicarbonyl compounds.

  研究人员探索了纳米氧化锌作为一种可重复使用的异相催化剂，通过脲、异atin 和 1,3-二羰基化合物之间的三组分反应，实现螺吲哚的一步法合成。
• A new eco-friendly strategy for the synthesis of novel antimicrobial spiro-oxindole derivatives via supramolecular catalysis
  作者：Shyam Babu Singh、Kamleshwar Tiwari、Pankaj Kumar Verma、Madhulika Srivastava、Kamla Prasad Tiwari、Jagdamba Singh

  DOI：10.1080/10610278.2012.761341

  日期：2013.5.1

  Novel spiro-oxindole derivatives were synthesised by one-pot multicomponent reaction using isatins, urea and 1,3-dicarbonyls. -Cyclodextrin, an oligosaccharide, catalysed the reaction and can be reused for further reaction after recovery. This developed synthetic route is environmentally benign in which water is used as solvent to produce excellent yields of products. The synthesised compounds were evaluated for their antimicrobial activities against two bacteria and two fungi. All the synthesised spiro-oxindoles exhibit significant antimicrobial activity.
• Novel One-Pot Synthesis of New Oxindole Derivatives Catalyzed by PTSA
  作者：Maliheh Khorshidi、Majid M. Heravi、Yahia S. Beheshtia、Bita Baghernejad

  DOI：10.1080/00397911.2010.515364

  日期：2011.10

  Abstract The one-pot synthesis of spirooxindoles via three-component reaction of urea, isatin, and 1,3-dicarbonyl compounds in the presence of a catalytic amount of p-toluenesulfonic acid in acetonitrile has been carried out.

  摘要 在乙腈中，在催化量的对甲苯磺酸存在下，通过尿素、靛红和1,3-二羰基化合物的三组分反应，一锅法合成螺环吲哚。