3,4-dihydro-3,3-dimethyl-13-(3,4-dimethoxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione | 1204395-09-4

• 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: 3,4-dihydro-3,3-dimethyl-13-(3,4-dimethoxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione
• 英文别名: 13-(3,4-dimethoxyphenyl)-3,3-dimethyl-4,13-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1204395-09-4
• 化学式: C₂₅H₂₄N₂O₅
• 分子量: 432.476
• InChiKey: RBISISREVCBPHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.9h， 生成 3,4-dihydro-3,3-dimethyl-13-(3,4-dimethoxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione
  参考文献：
  名称：

  SO 3 H-官能化介孔二氧化硅材料作为固体酸催化剂，可轻松，无溶剂地合成2 H-吲唑并[ 2,1- b ]酞嗪-1,6,11-三酮衍生物

  摘要：

  SO 3 H-官能化介孔二氧化硅材料（SO 3 H-FMSM）作为一种高效，温和，可回收和环保的非均相介孔纳米催化剂，被用于合成2 H-吲唑并[ 2,1 - b ]邻苯二甲酰1.6。 1,11-三酮衍生物在无溶剂热（SF）条件下的2,3-二氢邻苯二甲酸-1,4-二酮，二甲酮和苯甲醛衍生物的一锅三组分缩合反应中，具有优异的收率和较短的反应时间。

  DOI：

  10.1039/c5nj01733e

文献信息

• β -Cyclodextrin as a supramolecular catalyst for the synthesis of 2 H -indazolo[2,1- b ]phthalazine-trione derivatives in water and their antimicrobial activities
  作者：Asha V. Chate、Priyanka K. Bhadke、Manisha A. Khande、Jaiprakash N. Sangshetti、Charansingh H. Gill

  DOI：10.1016/j.cclet.2017.03.007

  日期：2017.7

  been developed for the synthesis of 2 H -indazolo[2,1- b ]phthalazine-triones derivatives by employing 15 mol% β -cyclodextrin via a one-pot multicomponent reaction of aldehyde, dimedone, hydrazine hydrate with succinic anhydride/phthalic anhydride in water at 80 °C for first time. The catalyst could be recovered and reused for four consecutive cycles without appreciable loss in catalytic activity and

  摘要开发了一种高效，绿色的方法，通过醛，二甲酮，水合肼的一锅多组分反应，使用15 mol％β-环糊精，合成2 H-吲哚并[2,1-b]邻苯二甲酰基-三酮衍生物。第一次在80°C的水中加入琥珀酸酐/邻苯二甲酸酐。该催化剂可以连续四个循环回收和再利用，而催化活性没有明显损失，并且可以评估其对不同革兰氏阳性和革兰氏阴性细菌菌株的体外抗菌活性。筛选研究的结果表明，化合物6d，6f和7n表现出对大肠杆菌的优异活性。而化合物6f和6h表现出优异的抗铜绿假单胞菌和化合物6c的活性，与氨苄青霉素（标准对照）相比，化合物6a和6e再次显示出对金黄色葡萄球菌的优异活性，而化合物7o显示出对金黄色葡萄球菌和枯草芽孢杆菌的优异活性。结果表明，最大的化合物对细菌的生长具有中等程度的效力，而对标准药物的效力最高。
• Nano-silica supported acidic ionic liquid as an efficient catalyst for the multi-component synthesis of indazolophthalazine-triones and bis-indazolophthalazine-triones
  作者：Shirin Safaei、Iraj Mohammadpoor-Baltork、Ahmad Reza Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani

  DOI：10.1039/c3cy00344b

  日期：——

  A supported ionic liquid bearing sulfonic acid groups was synthesized by anchoring 3-sulfopropyl-1-(3-propyltrimethoxysilane)imidazolium hydrogen sulfate onto nano-silica and characterized by FT-IR spectroscopy, elemental analysis and scanning electron microscopy (SEM) techniques. This catalyst was used for the efficient one-pot multi-component synthesis of indazolophthalazine-triones and bis-indazolophthalazine-triones. Moreover, the catalyst could be reused at least seven times without any significant loss of activity.

  一种带有磺酸基团的支持性离子液体通过将3-磺丙基-1-(3-丙基三甲氧基硅烷)咪唑鎓硫酸氢盐锚定在纳米二氧化硅上合成，并通过FT-IR光谱、元素分析和扫描电子显微镜(SEM)技术进行了表征。这种催化剂用于高效的一锅法多组分合成吲唑并吡嗪三酮和双吲唑并吡嗪三酮。此外，该催化剂至少可以重复使用七次而没有任何明显的活性损失。
• Magnetic Nanoparticle Immobilized N-Propylsulfamic Acid as a Recyclable and Efficient Nanocatalyst for the Synthesis of 2H-indazolo[2,1-b]phthalazine-triones in Solvent-Free Conditions: Comparison with Sulfamic Acid
  作者：Amin Rostami、Bahman Tahmasbi、Ako Yari

  DOI：10.5012/bkcs.2013.34.5.1521

  日期：2013.5.20

  N-Propylsulfamic acid supported onto magnetic $Fe_3O_4$ nanoparticles (MNPs-PSA) was used as an efficient and magnetically recoverable catalyst for synthesis of 2H-Indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives from the three-component, one-pot condensation reaction of phthalhydrazide, aromatic aldehydes and cyclic 1,3-diones, in good to excellent yields at $100^\circ}C$ under solvent-free conditions. The catalyst was easily separated with the assistance of an external magnetic field from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency. In order to compare, the synthesis of 2H-Indazolo[ 2,1-b]phthalazine-1,6,11(13H)-trione derivatives in the presence of catalytic amount of sulfamic acid (SA) under same reaction condition was also reported.

  负载在磁性$Fe_3O_4$纳米颗粒上的N-丙基磺酸胺(MNPs-PSA)被用作一种高效且可磁性回收的催化剂，用于从酞酰肼、芳香醛和环状1,3-二酮的三组分一锅法缩合反应中合成2H-吲唑[2,1-b]酞嗪-1,6,11(13H)-三酮衍生物，在无溶剂条件下于$100^\circ}C$下得到良好至优异的产率。催化剂借助外部磁场轻松地从反应混合物中分离出来，并在连续多次循环使用中保持其催化效率无显著损失。为了进行比较，同样反应条件下使用硫酸胺(SA)催化量的2H-吲唑[2,1-b]酞嗪-1,6,11(13H)-三酮衍生物的合成也进行了报道。
• A new natural based ionic liquid 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate as an efficient catalyst for the preparation of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones
  作者：Reza Tayebee、Malihe Jomei、Behrooz Maleki、Maryam Kargar Razi、Hojat Veisi、Mohammad Bakherad

  DOI：10.1016/j.molliq.2015.02.021

  日期：2015.6

  A novel Brønsted acidic ionic liquid 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate [Simp]HSO4 was synthesized via the reaction of caffeine with chlorosulfonic acid and was characterized by studying FT-IR, 1H NMR, 13C NMR, UV–Vis, and fluorescence spectra. Then, the prepared ionic liquid was utilized as an efficient catalyst for the preparation of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione

  通过咖啡因与氯磺酸的反应合成了一种新型的布朗斯台德酸性离子液体3-磺酸1-咪唑并吡啶鎓硫酸氢盐[Simp] HSO 4，并通过FT-IR，1 H NMR，13 C NMR，UV-Vis进行了表征和荧光光谱。然后，将制备的离子液体用作通过一锅多醛缩合制备2H-吲唑并[2,1-b]酞嗪-1,6,11（13H）-三酮衍生物的有效催化剂。 ，邻苯二甲酰肼和二甲酮在无溶剂的条件下使用。该催化剂的高布朗斯台德酸性功能主要源自SO 3 H基团的双重氢键结合能力。
• Magnetic nanoparticles Fe3O4-supported guanidine as an efficient nanocatalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions
  作者：Bahareh Atashkar、Amin Rostami、Hoshyar Gholami、Bahman Tahmasbi

  DOI：10.1007/s11164-013-1480-x

  日期：2015.6

  Here, the application of guanidine supported on magnetic nanoparticles Fe3O4 (MNPs-guanidine) as a novel magnetically separable base nanocatalyst is described. We have investigated the application of this new catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives from the three-component, one-pot condensation reaction of phthalhydrazide, cyclic 1,3-dicarbonyl, and aromatic aldehydes under solvent-free conditions. The products were obtained in short reaction times with good to high yields. The supported catalyst could be simply separated and recovered from the reaction mixture with the assistance of an external magnet and reused 18 times with little loss of activity.

  这里描述了氨基脲负载在磁性纳米颗粒Fe3O4上的应用（MNPs-guanidine），作为一种新型的可磁性分离的碱性纳米催化剂。我们研究了这种新催化剂在无溶剂条件下，通过邻苯二酸肼、环状1,3-二羰基化合物和芳香醛的三组分、一步缩合反应合成2H-indazolo[2,1-b]phthalazine-trione衍生物的应用。产物在短反应时间内获得，产率良好至很高。负载催化剂可以通过外部磁铁简单地从反应混合物中分离和回收，并可重复使用18次，活性损失很少。