3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H, 13H)-trione | 1173891-40-1

• 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: 3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-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-(3,4,5-trimethoxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione；3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione；2,3,4,13-tetrahydro-3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-indazolo[2,1-b]ph-thalazine-1,6,11-trione；3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-2,3,4,13-tetrahydroindazolo[2,1-b]phthalazine-1,6,11-trione；3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-3,4-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione；3,4-dihydro-13-(3,4,5-trimethoxyphenyl)-3,3-dimethyl-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione；2,3,4,13-Tetrahydro-3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-indazolo[2,1-b]phthalazine-1,6,11-trione；3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-4,13-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1173891-40-1
• 化学式: C₂₆H₂₆N₂O₆
• 分子量: 462.502
• InChiKey: RZEHJLPUEDIMDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

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 3,3-dimethyl-13-(3,4,5-trimethoxyphenyl)-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

• 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。
• TMSCl-mediated one-pot, three-component synthesis of 2<i>H</i>-indazolo[2,1-<i>b</i>]phthalazine-triones
  作者：Lingaiah Nagarapu、Rajashaker Bantu、Hari Babu Mereyala

  DOI：10.1002/jhet.135

  日期：2009.7

  A simple, efficient, and cost-effective method for the synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives by a one-pot, three-component condensation reaction of phthalazide, dimedone, or 1,3-cyclohexanedione and aromatic aldehydes under CH3CN/DMF (8:2) media at 80°C for 30–60 min in the presence of trimethylsilyl chloride (TMSCl) is described. J. Heterocyclic Chem., (2009).

  一种通过一锅三组分缩合反应合成2 H-吲哚并[ 2,1- b ]邻苯二甲酰1,6,11（13 H）-三酮衍生物的简单，高效且经济高效的方法酞嗪，双甲酮，或1,3-环己二酮和芳香醛在CH 3 CN / DMF（8：2）介质中在80°C下存在30-60分钟的条件下描述了三甲基甲硅烷基氯（TMSCl）。J.杂环化​​学，（2009）。
• Silica-supported tungstic acid (STA): A recyclable catalyst for the synthesis of <i>1H</i>-indazolo [1,2-<i>b</i>]phthalazine-trione and spiro-triazolo[1,2-<i>a</i>]indazole-tetraone derivatives under solvent-free condition
  作者：Amol Maruti Jadhav、Sandip Gangadhar Balwe、Yeon Tae Jeong

  DOI：10.1080/10426507.2019.1661414

  日期：2020.3.3

  Abstract An efficient one-pot synthesis of 1 H-indazolo[1,2-b]phthalazine-trione and spiro-triazolo[1,2-a]indazole-tetraone derivatives via three-component condensation reaction of phthalhydrazide or 4-phenylurazole, aldehydes or isatins and dimedone in the presence of a catalytic amount of silica-supported tungstic acid (STA), as a heterogeneous solid acid catalyst under solvent-free conditions is

  摘要 通过邻苯二甲酰肼或4-苯脲三组分缩合反应，高效一锅法合成1 H-吲唑并[1,2-b]酞嗪-三酮和螺-三唑并[1,2-a]吲唑-四酮衍生物，醛或靛红和二甲酮在催化量的二氧化硅负载钨酸 (STA) 存在下，作为无溶剂条件下的多相固体酸催化剂。这种生态友好的协议提供了几个优点，例如具有高产率、反应时间短、处理简单、回收和可重复使用的催化剂具有广泛的可用底物范围的具有成本效益的程序。这使得该协议具有可持续性和经济性。图形概要