3,4-dihydro-3,3-dimethyl-13-(4-bromophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione | 1017238-95-7

• 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-(4-bromophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione
• 英文别名: 13-(4-bromophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione；13-(4-bromophenyl)-3,3-dimethyl-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione；13-(4-Bromophenyl)-3,3-dimethyl-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione；13-(4-bromophenyl)-3,3-dimethyl-4,13-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1017238-95-7
• 化学式: C₂₃H₁₉BrN₂O₃
• 分子量: 451.319
• InChiKey: LIWDUCKAKRDNFC-UHFFFAOYSA-N

物化性质

• 熔点：
  265-267 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  583.8±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 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

• 作为反应物：
  描述：

  3,4-dihydro-3,3-dimethyl-13-(4-bromophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 以 水 、 乙腈 为溶剂， 反应 25.0h， 生成 13-(4-bromophenyl)-3, 3-dimethyl-3, 4-dihydro-1H-indazolo [1, 2-b] phthalazine 1, 6, 11 (2H, 13H)-trione
  参考文献：
  名称：

  Synthesis of phthalazine derivative based organic nanoflakes in aqueous solvent as a potential nano-anticancer agent: A new approach in medical field

  摘要：

  A simple phthalazine derivative 13-(4-bromophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[1,2-b] phthalazine-1,6,11(2H,13H)-trione (IDP) was synthesized by Knoevenagel condensation with Michael addition reaction. The present articles deals with preparation of highly fluorescent nanoparticles as prepared drug (IDP) by simple reprecipitation method using single aqueous solvent. The DLS measurement predicted the 150 nm size of a synthesized IDP NPs. Furthermore UV-Visible and fluorescence spectroscopy measurement showed a distinct peak for IDP NPs from their parent molecule. Scanning Electron Microscopy (SEM) microphotograph of air dried film of nanoparticles exhibited nanoflakes type and feathery morphology. The highly fluorescent nature of IDP NPs ultimately revealed in high quantum yield than IDP parent molecule. These fluorescent organic nanoflakes then further applied as anticancer agent. Interestingly it showed better activity than IDP molecules. Thus this is the first report to use organic nanoflakes as an anticancer agent, which may open new avenues in medical field's and related sciences. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127156
• 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 6.83h， 生成 3,4-dihydro-3,3-dimethyl-13-(4-bromophenyl)-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

• 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。
• Novel ionic liquid <i>N,N</i>-diethyl-<i>N</i>-sulfoethanaminium hydrogen sulfate: Design, characterization, and application as a highly efficient catalyst for the production of triazolo[1,2-<i>a</i>]indazole-triones and 2<i>H</i>-indazolo[2,1-<i>b</i>]phthalazine-triones
  作者：Abdolkarim Zare、Fatemeh Masihpour

  DOI：10.1080/10426507.2016.1149853

  日期：2016.8.2

  mass data. Then, its catalytic activity was examined for the preparation of triazolo[1,2-a]-indazole-triones and 2H-indazolo[2,1-b]phthalazine-triones by the one-pot multi-component condensation of arylaldehydes with dimedone and 4-phenylurazole/2,3-dihydrophthalazine-1,4-dione under solvent-free conditions. [Et3N-SO3H]HSO4 efficiently promoted the reaction to afford the products in high yields and

  图形摘要 摘要合成了一种新型布朗斯台德酸性离子液体，即 N,N-二乙基-N-磺胺硫酸氢盐 ([Et3N-SO3H]HSO4)，并使用 FT-IR、1H NMR、13C NMR 和质谱数据进行表征。然后，通过芳醛与二甲酮的一锅多组分缩合反应制备三唑并[1,2-a]-吲唑-三酮和2H-吲唑并[2,1-b]酞嗪-三酮的催化活性和 4-苯基脲唑/2,3-二氢酞嗪-1,4-二酮在无溶剂条件下。[Et3N-SO3H]HSO4 有效地促进了反应，以高产率和短反应时间提供了产物。
• Efficient synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives using succinimidinium N-sulfonic acid hydrogen sulfate as a new ionic liquid catalyst
  作者：Masoumeh Abedini、Farhad Shirini、Javad Mohammad-Alinejad Omran

  DOI：10.1016/j.molliq.2015.09.014

  日期：2015.12

  Succinimidinium N-sulfonic acid hydrogen sulfate is prepared as a new ionic liquid and characterized with a variety of techniques including FT-IR, 1H and 13C NMR, SEM, mass spectra method as well as Hammett acidity function. After identification, this reagent was used as an efficient catalyst for the multi-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives. The simple work-up, mild

  琥珀酰亚胺N-磺酸硫酸氢盐被制备为新型离子液体，并通过多种技术进行表征，包括FT-IR，1 H和13 C NMR，SEM，质谱法以及哈米特酸度函数。鉴定后，该试剂用作2 H-吲哚并[ 2,1 - b ]邻苯二甲腈-三酮衍生物的多组分合成的有效催化剂。简单的后处理，温和的反应条件，优异的收率和相对较短的反应时间是该方案的显着优势。另外，该离子液体可以循环使用几次而其催化活性没有明显降低。
• Solvent-free sonochemical one-pot three-component synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-triones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
  作者：Gaurav Shukla、Rajiv K. Verma、Girijesh K. Verma、Maya Shankar Singh

  DOI：10.1016/j.tetlet.2011.10.136

  日期：2011.12

  A rapid and efficient one-pot three-component protocol for the synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-triones 4 and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones 6 has been developed by domino coupling of phthalhydrazide, 1,3-diketones, and aldehydes under solvent-free conditions at 80 °C as well as under solvent-free ultrasound irradiation at room temperature promoted by (S)-camphorsulfonic

  一种快速高效的一锅三组分规程，用于合成2 H-吲唑并[2,1- b ]邻苯并-1,6,11-三酮4和1 H-吡唑并[1,2- b ]邻苯并-通过在80°C下无溶剂条件下以及（S）促进的室温下在无溶剂超声辐照下，将邻苯二甲酰肼，1,3-二酮和醛进行多米诺偶联，开发了5,10-二酮6。樟脑磺酸。
• 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。