13-(2,4-dichlorophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione | 1173891-44-5

• 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: 13-(2,4-dichlorophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione
• 英文别名: 3,4-dihydro-3,3-dimethyl-13-(2,4-dichlorophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione；13-(2,4-dichlorophenyl)-3,3-dimethyl-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione；13-(2,4-dichlorophenyl)-3,3-dimethyl-4,13-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1173891-44-5
• 化学式: C₂₃H₁₈Cl₂N₂O₃
• 分子量: 441.314
• InChiKey: DRJIZGVGLVERBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯酐 在 (4-sulfobutyl)-tris(4-sulfophenyl)phosphonium hydrogen sulfate 、 一水合肼 作用下， 反应 0.13h， 生成 13-(2,4-dichlorophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione
  参考文献：
  名称：

  Four-component synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives

  摘要：

  通过使用可重复使用的离子液体、2-吡咯烷酮氢硫酸盐、(4-磺丁基)三(4-磺苯基)膦氢硫酸盐和三苯基(丙基-3-磺酰基)膦对甲苯磺酸盐作为酸性催化剂,研究了二甲酮、芳基醛、水合肼和邻苯二甲酸酐四组分缩合制备2H-吲唑并[2,1-b]酞嗪-1,6,11(13H)-三酮衍生物的高效合成方法。

  DOI：

  10.1016/j.crci.2012.09.005

文献信息

• An efficient and green one-pot synthesis of indazolo[1,2-b]-phthalazinetriones via three-component reaction of aldehydes, dimedone, and phthalhydrazide using Fe3O4@SiO2 core–shell nanoparticles
  作者：Boshra Mirhosseini-Eshkevari、Mohammad Ali Ghasemzadeh、Javad Safaei-Ghomi

  DOI：10.1007/s11164-014-1854-8

  日期：2015.10

  An efficient and eco-friendly procedure for the one-pot synthesis of biologically active heterocyclic compounds including indazolo[1,2- b ]-phthalazinetriones has been developed in the presence of Fe3O4@SiO2 nanoparticles. The multicomponent reactions of aldehydes, dimedone, and phthalhydrazide were carried out under solvent-free conditions to obtain some indazolo[1,2- b ]-phthalazinetrione derivatives

  在Fe 3 O 4 @SiO 2纳米粒子的存在下，已经开发出了一种有效且环保的方法，用于一锅合成生物活性杂环化合物，包括吲哚并[1,2- b ]-酞嗪三酮。在无溶剂条件下进行醛，二甲酮和邻苯二甲酰肼的多组分反应，得到一些吲唑并[1,2- b ]-酞嗪三酮衍生物。本方法提供了许多优点，例如优异的收率，简单的后处理，低的反应时间，容易的催化剂分离和很少的催化剂负载。
• Solvent-free, sonochemical, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones and 1H-pyrazolo[1,2-b]phthalazine-diones catalyzed by Fe3O4@SiO2-imid-PMAn magnetic nanoparticles
  作者：Mohsen Esmaeilpour、Jaber Javidi、Fatemeh Nowroozi Dodeji、Saeed Zahmatkesh

  DOI：10.1007/s11164-016-2462-6

  日期：2021.6

  A practical and green method for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones and 1H-pyrazolo[1,2-b]phthalazine-diones using Fe3O4@SiO2-imid-PMAn nanoparticles as an eco-friendly magnetic catalyst from the four-component condensation, solvent-free reaction of phthalic anhydride, hydrazinium hydroxide, 1,3-diketones, and aldehydes under thermal or ultrasound irradiation at room temperature

  一种使用 Fe 3 O 4 @SiO 2 -imid-PMA合成 2 H -吲唑并[2,1- b ]酞嗪三酮和 1 H -吡唑并[1,2- b ]酞嗪二酮的实用绿色方法n描述了纳米粒子作为一种环保磁性催化剂，来自邻苯二甲酸酐、氢氧化肼、1,3-二酮和醛的四组分缩合、无溶剂反应，在室温下进行热或超声辐照。这种新方法具有显着的优点，例如操作简单、产率高、反应时间短以及没有任何繁琐的后处理或纯化。此外，催化剂的热稳定性、易于制备和分离使其成为一种良好的多相体系，是其他多相催化剂的有用替代品。此外，催化剂可以很容易地通过磁场回收并重复使用八个连续的反应循环而不会显着损失活性。
• One-pot synthesis of aliphatic and aromatic 2H-indazolo[2,1-b]phthalazine-triones catalyzed by N-halosulfonamides under solvent-free conditions
  作者：Ramin Ghorbani-Vaghei、Rahman Karimi-Nami、Zahra Toghraei-Semiromi、Mostafa Amiri、Mehdi Ghavidel

  DOI：10.1016/j.tet.2011.01.024

  日期：2011.3

  N, N, N′, N′-Tetrabromobenzene-1,3-disulfonamide and poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) were used as efficient catalysts for the one-pot synthesis of aliphatic and aromatic 2H-indazolo[2,1-b]phthalazine-triones in excellent yields from aldehydes, phthalhydrazide, and dimedone at 80–100 °C under solvent-free conditions.

  N，N，N '，N'-四溴苯-1,3-二磺酰胺和聚（N-溴-N-乙基苯-1,3-二磺酰胺）被用作一锅合成脂肪族和芳香族2的有效催化剂在80–100°C的无溶剂条件下，H-吲哚并[2,1- b ]酞嗪三酮以优异的产率从醛，邻苯二甲酰肼和二甲基酮产生。
• An efficient and recyclable bifunctional acid–base ionic liquid for synthesis of 1H-indazolo[1,2-b]phthalazinetriones
  作者：Davood Habibi、Atefeh Shamsian

  DOI：10.1007/s11164-014-1736-0

  日期：2015.9

  A bifunctional ionic liquid, 1,4-dimethyl(4-sulfobutyl)piperazinium hydrogen sulfate ([DMSBP][HSO4], 1), containing both acid and basic sites was prepared. This ionic liquid was used as a homogeneous and reusable catalyst and efficiently promoted synthesis of 1H-indazolo[1,2-b]phthalazinetriones (5a–m) in a one-pot, four-component condensation reaction of phthalic anhydride, hydrazinium hydroxide, dimedone, and aromatic aldehydes under solvent-free conditions at 80 °C. Advantages of the method include short reaction time, high yields, and simple purification.

  制备了一种含有酸性和碱性位点的双功能离子液体1,4-二甲基（4-磺丁基）哌嗪硫酸氢盐（[DMSBP][HSO4], 1）。该离子液体作为均相可重复使用的催化剂，在无溶剂条件下，于80°C下高效促进了邻苯二甲酸酐、水合肼、二甲基乙二肟和芳香醛的四组分一锅法缩合反应，合成了1H-吲唑并[1,2-b]酞嗪三酮类化合物（5a-m）。该方法的优点包括反应时间短、产率高和纯化简单。
• 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。