2,3,4,13-tetrahydro-13-(3-hydroxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione | 1187744-34-8

• 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: 2,3,4,13-tetrahydro-13-(3-hydroxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione
• 英文别名: 13-(3-hydroxyphenyl)-2,3,4,13-tetrahydroindazolo[2,1-b]phthalazine-1,6,11-trione；13-(3-Hydroxyphenyl)-2,3,4,13-tetrahydroindazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1187744-34-8
• 化学式: C₂₁H₁₆N₂O₄
• 分子量: 360.369
• InChiKey: ZAXGYNWXRYGNHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻苯二甲酰肼 、 1,3-环己二酮 、 间羟基苯甲醛 在 β‑cyclodextrin sulfonic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以94%的产率得到2,3,4,13-tetrahydro-13-(3-hydroxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione
  参考文献：
  名称：

  β-环糊精-SO 3 H：无溶剂条件下一锅合成2H-吲唑并[2,1-b]邻苯二甲腈-三酮的最有效催化剂

  摘要：

  摘要 通过简单地将各种醛与环状化合物结合，已开发出一种环境友好的高效方法，用于合成一系列以β-环糊精-SO 3 H为催化剂的2H-吲唑并[2,1-b]邻苯二甲腈-三酮衍生物。1,3-二酮和邻苯二甲酰肼在无溶剂条件下使用。这种方法的优点是原子经济性高，操作简单，反应时间短，收敛性好，自动化程度高。 图形概要 首次开发了一种绿色环保，高效且快速的方法，以β-环糊精-SO 3 H作为可循环利用的催化剂来合成2H-吲唑并[2,1-b]酞嗪-三酮衍生物。

  DOI：

  10.1007/s11164-015-2113-3

文献信息

• 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。
• Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions
  作者：Mazaahir Kidwai、Anwar Jahan、Ritika Chauhan、Neeraj Kumar Mishra

  DOI：10.1016/j.tetlet.2012.01.095

  日期：2012.4

  for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones via one-pot, three-component condensation reaction of aromatic aldehydes with 1,3-dicarbonyl compounds and phthalhydrazide using reusable dodecylphosphonic acid (DPA) as heterogeneous solid acid catalyst under solvent-free conditions. This protocol provides a novel and improved method for obtaining 2H-indazolo[2,1-b]phthalazine-triones in terms

  已开发出一种新的绿色方案，用于使用可重复使用的十二烷基膦酸酯通过芳香醛与1,3-二羰基化合物和邻苯二甲酰肼的一锅三组分缩合反应来合成2 H-吲唑并[ 2,1 - b ]邻苯二甲酮三酮。在无溶剂条件下作为多相固体酸催化剂的酸（DPA）。该方案提供了一种新颖且改进的方法，该方法以良好的收率和很少的催化剂载量获得了2 H-吲哚并[ 2,1 - b ]邻苯二嗪-三酮。
• 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）。
• Application of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an efficient polymer-supported catalyst in the rapid synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products
  作者：Seyedeh Zahra Dalil Heirati、Farhad Shirini、Abdollah Fallah Shojaei

  DOI：10.1007/s13738-020-01982-3

  日期：2020.12

  used as a catalyst for the synthesis of a series of 2H-indazolo[2,1-b]phthalazine-triones and Biginelli-like products. It was observed that only 10 mg of the catalyst was enough to catalyze these reactions under mild conditions, and the corresponding products were obtained in high to excellent yields. Moreover, the catalyst could be repeatedly used for at least five times without a noticeable decrease

  在这项工作中，使用O-磺酸聚（4-乙烯基吡咯烷鎓）氯化物（[PVP-SO]首次有效地合成了一系列2 H-吲唑并[2,1-b]邻苯二嗪三酮和类似Biginelli的产物。3 H] Cl）作为环保型聚合物负载型催化剂。首先，根据氯磺酸的量和磺化时间对催化剂的制备工艺进行优化，以得到最大酸度的催化剂。获得的[PVP-SO 3 H] Cl的最大酸度为3.31 mmol g -1。然后，将优化的[PVP-SO 3 H] Cl用作合成一系列2 H的催化剂-吲唑并[2,1-b]酞嗪三酮类和Biginelli样产品。观察到仅10mg的催化剂足以在温和的条件下催化这些反应，并且以高至优异的产率获得了相应的产物。此外，该催化剂可以重复使用至少五次而其催化活性没有明显降低。
• Synthesis of 2 H- indazolo[2,1- b ]phthalazine-1,6,11(13 H )-triones using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate {DABCO(HSO 3 ) 2 (HSO 4 ) 2 } as a new ionic liquid catalyst
  作者：Farhad Shirini、Mohaddeseh Safarpoor Nikoo Langarudi、Omid Goli-Jolodar

  DOI：10.1016/j.dyepig.2015.07.036

  日期：2015.12

  1,4-Disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate DABCO(HSO3)(2)(HSO4)(2)} as a new ionic liquid, is prepared and characterized by using different methods including FT-IR, NMR, Mass and SEM analysis as well as determination of the Hammett acidity function. This reagent can be used as an efficient catalyst for the promotion of the synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives as important biologically active compounds with pharmaceutical properties. All reactions are performed in the absence of solvent using small amounts of the catalyst. Easy preparation of the catalyst, simple and easy work-up, mild reaction conditions, green process, excellent yields and short reaction times are the most important advantages this of method. (C) 2015 Elsevier Ltd. All rights reserved.