13-(4-fluorophenyl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione | 1204395-16-3

• 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-(4-fluorophenyl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione
• CAS: 1204395-16-3
• 化学式: C₂₁H₁₅FN₂O₃
• 分子量: 362.36
• InChiKey: AOJOBMXMJQMMQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  邻苯二甲酰肼 、 对氟苯甲醛 、 1,3-环己二酮 在 Fe₃O₄ nanoparticles-supported N-propylsulfamic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.83h， 以89%的产率得到13-(4-fluorophenyl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.5012/bkcs.2013.34.5.1521

文献信息

• 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。
• Efficient one-pot syntheses of 2H-indazolo[2,1-b] phthalazine-triones by catalytic H2SO4 in water–ethanol or ionic liquid
  作者：Jitender M. Khurana、Devanshi Magoo

  DOI：10.1016/j.tetlet.2009.10.032

  日期：2009.12

  Sulfuric acid-catalyzed, three-component, one-pot condensation of phthalhydrazide, aromatic aldehydes and 1,3-dicarbonyl compounds has been reported for the synthesis of a series of 2H-indazolo[2,1-b] phthalazine-triones in water–ethanol or in ionic liquid. The protocol proves to be efficient and environmentally benign in terms of high yields, low reaction times, ease of recovery, and reusability of

  据报道，硫酸催化的三组分邻苯二甲酰肼，芳族醛和1,3-二羰基化合物的一锅缩合反应可用于合成一系列2 H-吲哚并[ 2,1 - b ]邻苯二甲腈-三酮。水-乙醇或离子液体中。该协议在高产率，低反应时间，易于回收和反应介质（离子液体）的可重复使用性方面被证明是有效且对环境无害的。
• Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives
  作者：Shihua Song、Xiang Deng、Zhi Guan、Yanhong He

  DOI：10.5560/znb.2012-0090

  日期：2012.7.1

  A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO₃HmIm]HSO₄) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

  本研究报道了一种在离子液体 4-(3-甲基-1-咪唑基)-1-丁烷磺酸硫酸氢盐（[BSO3HmIm]HSO4）催化下，通过邻苯二甲酰肼、1,3-二羰基化合物和醛的单锅三组分缩合反应合成邻苯二甲酰肼衍生物的简单方法。在 PEG 600（聚乙二醇 600）溶剂中，反应时间短，温度为 120 °C，即可获得良好甚至极佳的产率。事实证明，该策略既高效又环保。催化剂/溶剂系统可轻松回收并重复使用至少 5 次，而不会明显丧失活性