8-nitro-quinoline N-oxide | 14753-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-nitro-quinoline N-oxide
• 英文别名: 8-nitroquinoline 1-oxide；8-nitro-quinoline-1-oxide；8-Nitro-chinolin-1-oxid；8-Nitro-chinolin-1-oxyd；8-Nitrochinolin-1-oxid；8-nitro-1-oxidoquinolin-1-ium
• CAS: 14753-18-5
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: XKMPRDAFNNEZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-nitro-quinoline N-oxide 在 palladium on activated charcoal 氢气 、 苯甲酰氯 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 22.5h， 生成 2-aminomethylquinolin-8-ylamine
  参考文献：
  名称：

  Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites

  摘要：

  A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via H-1 NMR complexation studies in 5% DMSO-d(6)-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure -function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.

  DOI：

  10.1021/jo0501689
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 硝酸 作用下， 生成 8-nitro-quinoline N-oxide
  参考文献：
  名称：

  Tanida, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1079,1082

  摘要：

  DOI：

文献信息

• Hypervalent Iodine(III)‐Mediated Regioselective Cyanation of Quinoline <i>N</i> ‐Oxides with Trimethylsilyl Cyanide
  作者：Feng Xu、Yuqin Li、Xin Huang、Xinjie Fang、Zhuofei Li、Hongshuo Jiang、Jingyi Qiao、Wenyi Chu、Zhizhong Sun

  DOI：10.1002/adsc.201801185

  日期：2019.2

  A regioselective cyanation of quinoline N‐oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal‐free and base‐free reaction conditions to obtain 2‐cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N−O bond cleavage. The reaction system featured

  在无金属和无碱反应条件下，使用（二乙酰氧基碘）苯（PIDA）作为介导的高价碘（III）试剂，开发了用三甲基甲硅烷基氰化喹啉N-氧化物的区域选择性氰化反应，从而获得2-氰基喹啉。高效的PIDA试剂可以起到底物的活化剂和N-O键断裂促进剂的作用。该反应系统具有广泛的底物适用性和高收率的特点。该程序以克级放大以合成结核病（TB）抑制剂。最后，根据一些实验结果，提出了合理的氰化反应机理。
• Tricyclic benzimidazoles and their use as metabotropic glutamate receptor modulators
  申请人：Isaac Methvin

  公开号：US20070032469A1

  公开（公告）日：2007-02-08

  The invention provides for a compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein R 1 , R 2 , R 3 , A, B, D, m, n, x, and y are defined as described in the specification. The invention additionally provides a pharmaceutically composition comprising the compound of formula I, together with a method of using the same to treat or prevent neurological and psychiatric disorders. The compounds are useful in therapy related to the treatment or prevention of mGluR2 receptor-mediated disorders.

  该发明提供了一个式(I)的化合物或其药用盐：其中R1、R2、R3、A、B、D、m、n、x和y的定义如规范中所述。该发明还提供了一种包含式I化合物的药用组合物，以及使用该组合物来治疗或预防神经学和精神疾病的方法。这些化合物在与mGluR2受体介导的疾病的治疗或预防相关的治疗中是有用的。
• Cyano-Sacrificial (Arylthio)arylamination of Quinoline and Isoquinoline <i>N</i>-Oxides Using <i>N</i>-(2-(Arylthio)aryl)cyanamides
  作者：Ahalya Behera、Prasenjit Sau、Ashish Kumar Sahoo、Bhisma K. Patel

  DOI：10.1021/acs.joc.8b01797

  日期：2018.9.21

  arylthio-arylamination of quinoline and isoquinoline N-oxides has been achieved at the expense of a cyano (CN) group from N-(2-(arylthio)aryl)cyanamides. This reductive amination proceeds in one pot at 80 °C in the absence of any additives. This is a unique demonstration of aryl cyanamides serving as arylaminating agents on quinoline/isoquinoline N-oxides with concurrent autoreduction of N-oxide.

  以N-（2-（芳硫基）芳基）氰酰胺的氰基（CN）基团为代价，已经实现了喹啉和异喹啉N-氧化物的铜（I）催化的区域选择性芳硫基芳基化。在没有任何添加剂的情况下，该还原胺化反应在80°C的一个锅中进行。这是芳基氰酰胺在喹啉/异喹啉N-氧化物上同时芳构胺化并同时自动还原N-氧化物的独特例证。
• Nitration of Quinoline 1-Oxide: Mechanism of Regioselectivity.
  作者：Akihiro YOKOYAMA、Tomohiko OHWADA、Shinichi SAITO、Koichi SHUDO

  DOI：10.1248/cpb.45.279

  日期：——

  The acidity dependence of orientation in the nitration of quinoline 1-oxide was investigated by using the trifluoromethanesulfonic acid (TFSA)-trifluoroacetic acid (TFA) system and the antimony pentafluoride (SbF5)-TFSA system. These systems provide a wider range of acidity than that of aqueous sulfuric acid. Comparison of the behavior of quinoline 1-oxide and 1-methoxyquinolinium triflate in acidic and neutral media demonstrated that O-protonated quinoline 1-oxide is nitrated at the 5- and 8-positions, and the free (unprotonated) molecule is nitrated at the 4-position. This result is consistent with theoretical expectation. It was also discovered that nitration at the 5-position increasingly predominates over that at the 8-position as the acidity is increased.

  在1-氧化喹啉的硝化反应中，使用三氟甲磺酸（TFSA）-三氟乙酸（TFA）体系和五氟化锑（SbF5）-TFSA体系研究了酸度对取向的影响。这些体系提供了比水合硫酸更广泛的酸度范围。比较了喹啉1-氧化物和1-甲氧基喹啉四氟乙酸盐在酸性和中性介质中的行为，表明O-质子化的喹啉1-氧化物在5位和8位被硝化，而自由（未质子化）分子在4位被硝化。这个结果与理论预期一致。还发现，随着酸度的增加，5位的硝化反应越来越占优势，超过了8位的硝化反应。
• Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof
  申请人：Lim Mu'Ill

  公开号：US20060156485A1

  公开（公告）日：2006-07-20

  Compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and at least one bicyclic 6-6 (0:1, 0:2, 1:1, 1:2) aza heteroaromatic keratin dyeing compound with one or two N-oxides. A method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.

  用于氧化染色角蛋白纤维的组合物，包括适合染色的介质和至少一种含有一个或两个N-氧化物的双环6-6（0:1, 0:2, 1:1, 1:2）杂环芳香族角蛋白染色化合物。一种氧化染色角蛋白纤维的方法，包括在氧化剂存在下施用这种组合物，以足够时间发展所需的着色。