3-nitro-7,8,9,10-tetrahydro-6H-azepino[1,2-a]benzimidazole | 5381-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-nitro-7,8,9,10-tetrahydro-6H-azepino[1,2-a]benzimidazole
• 英文别名: 7,8,9,10-Tetrahydro-3-nitro-6H-azepino<1,2-a>benzimidazol；3-nitro-7,8,9,10-tetrahydro-6H-benzo[4,5]imidazo[1,2-a]azepine；3-nitro-5a,6,7,8,9,10-hexahydro-5H-benzo[4,5]imidazo[1,2-a]azepine；3-Nitro-7,8,9,10-tetrahydro-6H-benz[4,5]imidazo[1,2-a]azepin
• CAS: 5381-75-9
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: QNZVMYVXYISBET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2,4-Dinitrophenyl)-perhydroazepin 在 edetate disodium 、 tin(ll) chloride 、 mercury(II) oxide 作用下， 以 乙醇 为溶剂， 生成 3-nitro-7,8,9,10-tetrahydro-6H-azepino[1,2-a]benzimidazole
  参考文献：
  名称：

  Kondensierte Nitrobenzimidazole

  摘要：

  AbstractBei der Quecksilber(II)‐EDTA‐Dehydrierung von 2‐tert. Amino‐5‐nitroanilinen entstehen unter 4‐Elektronenentzug die entsprechenden Benzimidazole. Durch methodische Modifizierungen konnte die Ausbeute im Vergleich zu derjenigen bei Standardbedingungen erhöht werden.

  DOI：

  10.1002/ardp.19823150410

文献信息

• α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles
  作者：Chunling Yuan、Yingdai Zhao、Li Zheng

  DOI：10.1055/s-0039-1690226

  日期：2019.12

  The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C–N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.

  这里报告了α-D-半乳糖醛酸水合物（GalA）作为潜在的O-供体配体的首次应用。N-杂环化合物与芳基卤化物或芳基硼酸的C-N偶联可以轻松进行，并且具有良好的官能团容忍性和选择性特征。这些N-芳基唑允许快速获得几种药用中间体，并且也可以轻松转化为各种其他有趣的骨架。
• Iridium-catalyzed intramolecular C N and C O/S cross-coupling reactions: Preparation of benzoazole derivatives
  作者：Yajie Shi、Qifan Zhou、Fangyu Du、Yang Fu、Yang Du、Ting Fang、Guoliang Chen

  DOI：10.1016/j.tetlet.2019.151082

  日期：2019.10

  The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously

  使用KOAc和仅1mol％的催化剂已经有效地实现了铱催化的与邻卤代芳基酰胺或邻卤代芳基idine杂的分子内芳基碳杂交联反应。事实证明，[Ir（cod）Cl] 2具有更大的潜力，可以平稳地组装功能结构苯并咪唑，苯并恶唑和苯并噻唑，优于铜和钯催化的体系。同时，开发了一种5 g规模的简洁而有效的tafamidis合成方法。
• Thermal transformations of 2H-benzimidazole 1,3-dioxides
  作者：V. A. Samsonov、I. Yu. Bagryanskaya、Yu. V. Gatilov、V. A. Savel’ev

  DOI：10.1007/s11172-011-0257-x

  日期：2011.8

  Thermal transformations of 2H-benzimidazole 1,3-dioxides represented by spiro[2H-benz-imidazole-2,1′-cyclohexane] 1,3-dioxide and its 5-nitro derivative were studied. Their heating resulted in reversible isomerization to spiro[3H-[2,1,4]benzoxadiazine-3,1′-cyclohexane] 4-oxides. More prolonged heating of 2H-benzimidazole 1,3-dioxides caused sequential elimination of the first and then (at higher temperature) the second N-oxide oxygen atom to form 2H-benzimidazole derivatives, which upon further heating were transformed to 7,8,9,10-tetrahydro-6H-azepino[1,2-a]benzimidazoles. A scheme of the process was suggested, which described the experimental data obtained. Spiro[3H-[2,1,4]benzoxadiazine-3,1′-cyclohexane] 4-oxides on exposure to the sunlight were quantitatively transformed to 2H-benzimidazole 1,3-dioxides.

  对由螺[2H-苯并咪唑-2,1′-环己烷] 1,3-二氧化物及其5-硝基衍生物代表的2H-苯并咪唑1,3-二氧化物的热转化进行了研究。加热导致其可逆异构化为螺[3H-[2,1,4]苯并噁二嗪-3,1′-环己烷] 4-氧化物。对2H-苯并咪唑1,3-二氧化物的更长时间加热则导致第一个、然后（在更高温度下）第二个N-氧原子的顺序消除，形成2H-苯并咪唑衍生物，这些衍生物在进一步加热后转化为7,8,9,10-四氢-6H-氮杂环[1,2-a]苯并咪唑。提出了一个过程示意图，以描述获得的实验数据。螺[3H-[2,1,4]苯并噁二嗪-3,1′-环己烷] 4-氧化物在阳光照射下定量转化为2H-苯并咪唑1,3-二氧化物。
• Herbert, John A. L.; Iddon, Brian; Robinson, Andrew G., Journal of the Chemical Society. Perkin transactions I, 1988, p. 991 - 998
  作者：Herbert, John A. L.、Iddon, Brian、Robinson, Andrew G.、Suschitzky, Hans

  DOI：——

  日期：——
• Syntheses in the pyrido- and piperido-(1′ : 2′-1 : 2)benziminazole series
  作者：K. H. Saunders

  DOI：10.1039/jr9550003275

  日期：——