5'-bromo-8,8-dimethyl-2-thioxo-2,3,8,9-tetrahydrospiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-2',4,6(1H,7H)-trione | 1132760-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 5'-bromo-8,8-dimethyl-2-thioxo-2,3,8,9-tetrahydrospiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-2',4,6(1H,7H)-trione
• 英文别名: 5-bromo-8',8'-dimethyl-2'-sulfanylidenespiro[1H-indole-3,5'-7,9-dihydro-1H-chromeno[2,3-d]pyrimidine]-2,4',6'-trione
• CAS: 1132760-17-8
• 化学式: C₂₀H₁₆BrN₃O₄S
• 分子量: 474.335
• InChiKey: FHTZIPLTEWIWIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 5-溴靛红 、 5,5-二甲基-1,3-环己二酮 在 MnFe₂O₄-NH₂-2AB-Ni 作用下， 以 水 为溶剂， 反应 0.67h， 以90%的产率得到5'-bromo-8,8-dimethyl-2-thioxo-2,3,8,9-tetrahydrospiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-2',4,6(1H,7H)-trione
  参考文献：
  名称：

  MnFe₂O₄@NH₂@2AB-Ni: a novel, highly active, stable and magnetically recoverable nanocatalyst and use of this heterogeneous catalyst in green synthesis of spirooxindoles in water

  摘要：

  在这项研究中，采用共沉淀法合成了超顺磁性锰铁氧体纳米颗粒，并通过硅烷化反应用3-氨丙基三乙氧基硅烷（APTES）进行了包覆。锰铁氧体纳米颗粒由于异苯酸酐与氨基功能化MnFe2O4之间的反应而赋予了双齿配体。氨基功能化的纳米颗粒与醋酸镍反应，形成了固定化的镍复合物。最后，通过在水中绿色合成脊环氧喹啉，考察了所制备纳米颗粒的催化性质，结果表明它们具有优异的催化活性。催化剂的回收只需应用外部永久磁铁即可轻松实现。分离的催化剂在新的反应中重复使用，没有显著降低催化活性。

  DOI：

  10.1039/c4nj01182a

文献信息

• One-pot three-component synthesis of functionalized spirooxindoles in gluconic acid aqueous solution
  作者：Rui-Yun Guo、Ping Wang、Guo-Dong Wang、Li-Ping Mo、Zhan-Hui Zhang

  DOI：10.1016/j.tet.2012.12.081

  日期：2013.2

  A general, efficient, and green method for one-pot synthesis of functionalized spirooxindoles through three-component condensation reaction of isatins, cyclohexane-1,3-diones, and barbituric acids is described employing gluconic acid aqueous solution (GAAS) as a novel reaction medium and catalyst. The reaction medium could be recycled and reused several times without significant loss of its efficiency

  描述了一种利用葡糖酸水溶液（GAAS）通过靛红，环己烷-1,3-二酮和巴比妥酸的三组分缩合反应一锅合成官能化螺硫辛醇的通用，有效且绿色的方法。介质和催化剂。反应介质可以循环使用多次，而不会显着降低其效率。
• Alum (KAl(SO4)2·12H2O) Catalyzed Multicomponent Transformation: Simple, Efficient, and Green Route to Synthesis of Functionalized Spiro[chromeno[2,3-d]pyrimidine-5,3′-indoline]-tetraones in Ionic Liquid Media
  作者：Mojtaba Mirhosseini Moghaddam、Ayoob Bazgir、Akhondi Mohammad Mehdi、Ramin Ghahremanzadeh

  DOI：10.1002/cjoc.201280014

  日期：2012.3

  The combination of isatin, barbituric acid, and cyclohexane‐1,3‐dione derivatives in the presence of alum (KAl(SO4)2·12H2O) as a catalyst for 15 min was found to be a suitable and efficient method for the synthesis of spiro[chromeno[2,3‐d]pyrimidine‐5,3′‐indoline]‐tetraones.

  发现在明矾（KAl（SO 4）2 ·12H 2 O）作为催化剂存在下15分钟将Isatin，巴比妥酸和环己烷-1,3-二酮衍生物组合使用是一种合适且有效的方法螺[ chromeno [2,3 - d ]嘧啶-5,3'-二氢吲哚]-四酮的合成。
• MnFe₂O₄@NH₂@2AB-Ni: a novel, highly active, stable and magnetically recoverable nanocatalyst and use of this heterogeneous catalyst in green synthesis of spirooxindoles in water
  作者：Hossein Naeimi、Zahra Rashid、Amir-Hassan Zarnani、Ramin Ghahremanzadeh

  DOI：10.1039/c4nj01182a

  日期：——

  In this research, superparamagnetic manganese ferrite nanoparticles were synthesized following a co-precipitation method, and subsequently coated with 3-aminopropyltriethoxysilane (APTES) through a silanization reaction. Manganese ferrite nanoparticles afforded bidentate ligands as a result of the reaction between isatoic anhydride and amino-functionalized MnFe2O4. The amino-functionalized nanoparticles were treated with nickel acetate, giving the immobilized nickel complex. Finally, catalytic properties of the prepared nanoparticles were examined by a green synthesis of spirooxindoles in water and they showed excellent catalytic activity. Recovery of the catalyst was simply achieved by applying an external permanent magnet. The isolated catalyst was reused for new reaction runs without significant loss of catalytic activity.

  在这项研究中，采用共沉淀法合成了超顺磁性锰铁氧体纳米颗粒，并通过硅烷化反应用3-氨丙基三乙氧基硅烷（APTES）进行了包覆。锰铁氧体纳米颗粒由于异苯酸酐与氨基功能化MnFe2O4之间的反应而赋予了双齿配体。氨基功能化的纳米颗粒与醋酸镍反应，形成了固定化的镍复合物。最后，通过在水中绿色合成脊环氧喹啉，考察了所制备纳米颗粒的催化性质，结果表明它们具有优异的催化活性。催化剂的回收只需应用外部永久磁铁即可轻松实现。分离的催化剂在新的反应中重复使用，没有显著降低催化活性。
• One-Pot, Three-Component Synthesis of a Library of Spirooxindole-Pyrimidines Catalyzed by Magnetic Nanoparticle Supported Dodecyl Benzenesulfonic Acid in Aqueous Media
  作者：Jia Deng、Li-Ping Mo、Fei-Yang Zhao、Zhan-Hui Zhang、Shou-Xin Liu

  DOI：10.1021/co3000264

  日期：2012.5.14

  Dodecyl benzenesulfonic acid functionalized silica-coated magnetic nanoparticles (gamma-Fe2O3@SiO2-DDBSA) were readily prepared and identified as an efficient catalyst for the synthesis of a library of spirooxindole-pyrimidine derivatives by three-component condensation reaction of barbituric acids, isatins and cyclohexane-1,3-diones. The aqueous reaction medium, easy recovery of the catalyst using an external magnet, and high yields make the protocol sustainable and economic.
• 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。