3,7,7- trimethyl-1-phenyl-7,8-dihydro-1H-spiro[chromeno[2,3’-c]pyrazole-4,3-indoline]-2’,5(6H)-dione | 1246222-58-1

• 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-1-phenyl-7,8-dihydro-1H-spiro[chromeno[2,3’-c]pyrazole-4,3-indoline]-2’,5(6H)-dione
• 英文别名: 3,7,7-trimethyl-1-phenyl-7,8-dihydro-1H-spiro[chromeno[2,3-c]pyrazole-4,3'-indoline]-2',5(1'H,6H)-dione；3',7',7'-trimethyl-1'-phenylspiro[1H-indole-3,4'-6,8-dihydrochromeno[2,3-c]pyrazole]-2,5'-dione
• CAS: 1246222-58-1
• 化学式: C₂₆H₂₃N₃O₃
• 分子量: 425.487
• InChiKey: XJOMEOGZXNYCBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 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：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  靛红 、 5,5-二甲基-1,3-环己二酮 、 依达拉奉 在 silica-supported organocatalyst system based on L-proline 作用下， 以 水 为溶剂， 反应 1.5h， 以91%的产率得到3,7,7- trimethyl-1-phenyl-7,8-dihydro-1H-spiro[chromeno[2,3’-c]pyrazole-4,3-indoline]-2’,5(6H)-dione
  参考文献：
  名称：

  A new silica-supported organocatalyst based on L-proline: An efficient heterogeneous catalyst for one-pot synthesis of spiroindolones in water

  摘要：

  A simple and practical synthetic strategy for the synthesis of a novel silica-supported organocatalyst system based on L-proline (SSLP) has been developed. First, silica was treated with trimethoxy(vinyl)silane to produced a vinyl-silica (VS) substrate. Then, VS was oxidized using H2O2 to generate the silica-oxiran (SO) material. Finally, ring-opening of oxiranes in SO substrate with L-proline was resulted the production of SSLP catalyst. The catalytic performance of SSLP was evaluated in the three-component synthesis of spirooxindole derivatives via the condensation reaction of isatins and dicarbonyl compounds in water. All reactions were completed in short times and all products were obtained in good to excellent yields. Besides, SSLP could be recovered for 8 times without any additional treatments. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.07.009

文献信息

• A comparative study on the catalytic activity of Fe3O4@SiO2–SO3H and Fe3O4@SiO2–NH2 nanoparticles for the synthesis of spiro [chromeno [2, 3-c] pyrazole-4, 3′-indoline]-diones under mild conditions
  作者：Fatemeh Alemi-Tameh、Javad Safaei-Ghomi、Mohammad Mahmoudi-Hashemi、Raheleh Teymuri

  DOI：10.1007/s11164-016-2470-6

  日期：2016.7

  dispersive X-ray spectroscopy, and Fourier transform infrared spectroscopy. To compare the efficiency of the two prepared functionalized magnetic nanoparticles, they were employed as catalysts for the synthesis of spirooxindole containing chromene ring fragments in one-pot four-component reactions. Sulfuric acid-functionalized magnetic nanoparticles showed high catalytic activity in mild reaction conditions

  摘要 硫酸和（3-氨基丙基）-三乙氧基硅烷已成功连接到Fe 3 O 4 @SiO 2的核-壳结构上纳米粒子分开。通过振动样品磁力计，粉末X射线衍射，扫描电子显微镜，热重分析，能量色散X射线光谱和傅里叶变换红外光谱对制备的纳米颗粒进行表征。为了比较两种制备的官能化磁性纳米颗粒的效率，将它们用作在一锅四组分反应中合成含环己吲哚的亚甲基环片段的催化剂。硫酸官能化的磁性纳米粒子在温和的反应条件下，短的反应时间和优异的产物收率下显示出高催化活性。使用磁体可以轻松地分离出催化剂，并将其重复用于多个反应周期，而不会显着降低催化活性。 图形概要
• The one-pot four-component eco-friendly synthesis of spirooxindoles in deep eutectic solvent
  作者：Thokchom Jeeta Devi、Thokchom Prasanta Singh、Okram Mukherjee Singh

  DOI：10.1007/s12039-019-1730-6

  日期：2020.12

  Abstract An efficient and facile synthesis of spirooxindole derivatives bearing pyrano[2,3- c ]pyrazole moiety has been achieved using deep eutectic solvent (DES) promoting a four-component reaction. The protocol avoids the use of costly and toxic catalysts and organic solvents which encounters many side effects on the environment and human beings. The simplicity and versatility of this eco-friendly

  摘要使用深共熔溶剂（DES）促进四组分反应， 可以高效，轻松地合成带有吡喃并[2,3- c ]吡唑部分的螺并吲哚衍生物 。该方案避免了使用昂贵且有毒的催化剂和有机溶剂，而这种催化剂和有机溶剂会对环境和人类造成许多副作用。描述了这种环保绿色方法的简单性和多功能性。 摘要摘要本文介绍了 深共熔溶剂（DES）促进的螺四氮杂吲哚衍生物的生态友好合成，涉及四组分反应。该方法具有高度的可持续性，因为涉及到了易于获得且可生物降解的深共晶溶剂作为反应介质和促进剂。
• One-pot and three-component synthesis of spiro[chromeno[2,3-d] pyrimidine-5,3′-indoline]-diones and spiro[chromeno[2,3-c] pyrazole-4,3′-indoline]-diones
  作者：Ramin Ghahremanzadeh、Fatemeh Fereshtehnejad、Zahra Yasaei、Tayebeh Amanpour、Ayoob Bazgir

  DOI：10.1002/jhet.399

  日期：——

  Abstract magnified image A novel, clean, one‐pot and three‐component synthesis of new spiro[chromeno[2,3‐d]pyrimidine‐5,3′‐indoline]‐2′,6(7H)‐diones and spiro[chromeno[2,3‐c]pyrazole‐4,3′‐indoline]‐2′,5(6H)‐diones via cyclo‐condensation reaction of isatins, 1,3‐cyclohexadiones, and 2‐methylpyrimidine‐4,6‐diol or 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol, in aqueous media is reported. J. Heterocyclic Chem., (2010).
• A new silica-supported organocatalyst based on L-proline: An efficient heterogeneous catalyst for one-pot synthesis of spiroindolones in water
  作者：Ali Khalafi-Nezhad、Elham Shaikhi Shahidzadeh、Samira Sarikhani、Farhad Panahi

  DOI：10.1016/j.molcata.2013.07.009

  日期：2013.11

  A simple and practical synthetic strategy for the synthesis of a novel silica-supported organocatalyst system based on L-proline (SSLP) has been developed. First, silica was treated with trimethoxy(vinyl)silane to produced a vinyl-silica (VS) substrate. Then, VS was oxidized using H2O2 to generate the silica-oxiran (SO) material. Finally, ring-opening of oxiranes in SO substrate with L-proline was resulted the production of SSLP catalyst. The catalytic performance of SSLP was evaluated in the three-component synthesis of spirooxindole derivatives via the condensation reaction of isatins and dicarbonyl compounds in water. All reactions were completed in short times and all products were obtained in good to excellent yields. Besides, SSLP could be recovered for 8 times without any additional treatments. (C) 2013 Elsevier B.V. All rights reserved.