5-nitro-3',3',6',6'-tetramethyl-3',4',6',7'-tetrahydrospiro[indoline-3,9'-xanthene]-1',2,8'(2'H,5'H)-trione | 1093239-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-nitro-3',3',6',6'-tetramethyl-3',4',6',7'-tetrahydrospiro[indoline-3,9'-xanthene]-1',2,8'(2'H,5'H)-trione
• 英文别名: 3',3',6',6'-tetramethyl-5-nitrospiro[1H-indole-3,9'-2,4,5,7-tetrahydroxanthene]-1',2,8'-trione
• CAS: 1093239-15-6
• 化学式: C₂₄H₂₄N₂O₆
• 分子量: 436.464
• InChiKey: GIYYVULKCUYDSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-硝基靛红 、 5,5-二甲基-1,3-环己二酮 在 graphene oxide-supported dicationic ionic liquid 作用下， 以 水 为溶剂， 反应 0.5h， 以91%的产率得到5-nitro-3',3',6',6'-tetramethyl-3',4',6',7'-tetrahydrospiro[indoline-3,9'-xanthene]-1',2,8'(2'H,5'H)-trione
  参考文献：
  名称：

  氧化石墨烯负载的阳离子型离子液体催化高效合成水中螺[吲哚啉-3,9'-x吨]三酮和螺[chromene-4,3'-吲哚啉] -3-腈衍生物

  摘要：

  在本文中，开发了一种温和且高效的合成路线，用于使用氧化石墨烯合成螺[吲哚啉-3,9'-吨]三酮和螺[chromene-4,3'-吲哚啉] -3-腈负载的阳离子型离子液体（DIL @ GO）作为水性介质中的非均相催化剂。通过取代的靛红与1,3-二酮化合物（1,3-环己二酮/二甲酮）和螺[色烯-4,3'的一锅缩合反应，合成了靶向的螺[吲哚啉-3,9'-x吨]三酮衍生物-二氢吲哚] -3-腈衍生物是通过取代的靛红，丙二腈和可烯丙基的CH活化化合物（2-羟基萘-1,4-二酮/二甲酮）的一锅反应合成的。DIL @ GO催化剂在所有测试的反应中均表现出出色的催化能力，并在较短的反应时间内获得了优异的最终产物分离产率。另外，催化剂的非均质性质有助于通过离心分离催化剂，并且其具有可保留活性的多达五个连续反应循环的可重复使用性使该方法更为有利且对环境无害。 图形摘要

  DOI：

  10.1007/s11164-021-04405-x

文献信息

• Zinc(II)‐poly(urea‐formaldehyde) supported on magnetic nanoparticles: A hybrid nanocatalyst for green synthesis of spiropyrans, spiroxanthenes, and spiropyrimidines
  作者：Mohammad Ali Bodaghifard、Zahra Mousavi

  DOI：10.1002/aoc.5859

  日期：2020.10

  Zinc‐poly(urea‐formaldehyde) supported on magnetic nanoparticles (MNPs@SiO2@PUF@Zn) was successfully used for the synthesis of spirooxindolopyran and spirooxindoloxanthene derivatives in aqueous medium as an environmentally benign condition. High yields, short reaction times, green solvent, reusability without significant reduction in catalytic activity, and simple separation of the catalyst using an external magnet

  将金属离子固定在无机载体上具有非常有趣的生物学，工业和催化应用。在这项研究中，通过将醋酸锌固定在磁性CoFe 2 O 4 @SiO 2上负载的聚脲甲醛表面上，成功制造了CoFe 2 O 4 @SiO 2 @ PUF @ Zn（OAc）2纳米结构。纳米颗粒通过一层一层的组装。杂化纳米颗粒的结构通过傅里叶变换红外光谱，X射线衍射，热重分析，能量色散X射线光谱，电感耦合等离子体原子发射光谱，振动样品磁力分析，Brunauer-Emmett-Teller表面积分析，扫描进行表征电子显微镜和透射电子显微镜。磁性纳米颗粒（MNPs @ SiO 2）上负载的锌-聚（脲醛）（PUF @ Zn）作为一种环境友好的条件，已成功地用于在水性介质中合成螺并氧杂并吡喃和螺并恶多恶并蒽衍生物。该方法的优点是高收率，较短的反应时间，绿色溶剂，可重用性而不会显着降低催化活性，使用外磁体简单地分离催化剂以及环境相容性。
• An Efficient Synthesis of Spiro[indoline-3,9′-xanthene]trione Derivatives Catalyzed by Magnesium Perchlorate
  作者：Chunfeng Chen、Chunlei Lv、Jianfeng Liang、Jianqing Jin、Lijun Wang、Chunlei Wu、Runpu Shen

  DOI：10.3390/molecules22081295

  日期：——

  A simple and efficient method for the synthesis of spiro[indoline-3,9'-xanthene]trione derivatives by means of condensation between isatins and 1,3-cyclohexanedione in the presence of a catalytic amount of magnesium perchlorate at 80 °C in 50% aqueous ethanol medium has been described. Notably, the present method offers desirable advantages of good yields, simplicity of workup procedure, easy purification

  一种简单有效的方法，是在催化量的高氯酸镁于80°C，50的条件下，通过靛红与1,3-环己二酮之间的缩合，合成螺[吲哚啉-3,9'-黄嘌呤]三酮衍生物。已经描述了％乙醇水溶液介质。值得注意的是，本方法提供了期望的优点，即良好的产率，简化的后处理步骤，易于纯化以及减少的反应时间。
• A Clean Synthesis of Spiro[indoline-3,9'-xanthene]trione Derivatives
  作者：Somayeh Ahadi、Hamid Reza Khavasi、Ayoob Bazgir

  DOI：10.1248/cpb.56.1328

  日期：——

  A simple, clean and efficient method for the synthesis of spiro[indoline-3,9′-xanthene]trione derivatives and spiro[acenaphthene-1,9′-xanthene]-1′,2,8′(2′H,5′H)-trione by condensation reaction of dimedone and isatins or acenaphthene in aqueous media is reported.

  报告了一种简单、清洁、高效的方法，通过二酮与异噻吩或苊在水介质中的缩合反应，合成螺[吲哚啉-3,9′-氧杂蒽]三酮衍生物和螺[苊-1,9′-氧杂蒽]-1′,2,8′(2′H,5′H)-三酮。
• Synthesis of Spirooxindoles through Cyclocondensation of Isatin and Cyclic 1,3-Diones
  作者：Rahul Joshi、Anita Kumawat、Saurabh Singh、Tapta Kanchan Roy、Ram T. Pardasani

  DOI：10.1002/jhet.3217

  日期：2018.7

  A simple, clean, and efficient method for the synthesis of spirooxindole derivatives via condensation of isatin with enolizable cyclic β‐diketones has been developed. The use of water as a solvent allows avoiding the use of toxic organic solvents, which makes this reaction safe and environmentally friendly. The mechanism of the condensation reaction has been investigated using first‐principles‐based

  已开发出一种简单，干净，有效的方法，该方法通过将靛红与可烯丙基的环式β-二酮缩合来合成螺环吲哚衍生物。使用水作为溶剂可以避免使用有毒的有机溶剂，从而使该反应安全且对环境无害。缩合反应的机理已使用基于第一原理的密度泛函理论计算进行了研究。
• 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.