3,3-dimethyl-13-(naphthalen-2-yl)-3,4-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione | 1204395-08-3

• 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: 3,3-dimethyl-13-(naphthalen-2-yl)-3,4-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione
• 英文别名: 3,3-dimethyl-13-(naphthalen-2-yl)-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione；3,4-dihydro-3,3-dimethyl-13-(naphthalen-2-yl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione；2,3,4,13-tetrahydro-3,3-dimethyl-13-(naphthalen-2-yl)-indazolo[2,1-b]phtha-lazine-1,6,11-trione；3,3‑dimethyl‑13‑(naphthalen‑2‑yl)‑2,3,4,13‑tetrahydro‑1H‑indazolo[1,2‑b]phthalazine‑1,6,11‑trione；3,3-Dimethyl-13-(naphthalen-2-yl)-3,4-dihydro-1h-indazolo[1,2-b]phthalazine-1,6,11(2h,13h)-trione；3,3-dimethyl-13-naphthalen-2-yl-4,13-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11-trione
• CAS: 1204395-08-3
• 化学式: C₂₇H₂₂N₂O₃
• 分子量: 422.483
• InChiKey: AWDUJZRTTXCYOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 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 、 5,5-二甲基-1,3-环己二酮 、 2-萘甲醛 在 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 7305.0h， 以93%的产率得到3,3-dimethyl-13-(naphthalen-2-yl)-3,4-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione
  参考文献：
  名称：

  Fe3O4@SiO2-imid-催化的2H-吲唑并[2,1-b]酞嗪-三酮和1H-吡唑并[1,2-b]酞嗪-二酮的无溶剂、声化学、一锅四组分合成PMAn磁性纳米粒子

  摘要：

  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。

  DOI：

  10.1007/s11164-016-2462-6

文献信息

• Nano-silica supported acidic ionic liquid as an efficient catalyst for the multi-component synthesis of indazolophthalazine-triones and bis-indazolophthalazine-triones
  作者：Shirin Safaei、Iraj Mohammadpoor-Baltork、Ahmad Reza Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani

  DOI：10.1039/c3cy00344b

  日期：——

  A supported ionic liquid bearing sulfonic acid groups was synthesized by anchoring 3-sulfopropyl-1-(3-propyltrimethoxysilane)imidazolium hydrogen sulfate onto nano-silica and characterized by FT-IR spectroscopy, elemental analysis and scanning electron microscopy (SEM) techniques. This catalyst was used for the efficient one-pot multi-component synthesis of indazolophthalazine-triones and bis-indazolophthalazine-triones. Moreover, the catalyst could be reused at least seven times without any significant loss of activity.

  一种带有磺酸基团的支持性离子液体通过将3-磺丙基-1-(3-丙基三甲氧基硅烷)咪唑鎓硫酸氢盐锚定在纳米二氧化硅上合成，并通过FT-IR光谱、元素分析和扫描电子显微镜(SEM)技术进行了表征。这种催化剂用于高效的一锅法多组分合成吲唑并吡嗪三酮和双吲唑并吡嗪三酮。此外，该催化剂至少可以重复使用七次而没有任何明显的活性损失。
• 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。
• 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。