7-硝基喹啉 | 613-51-4

• 物质功能分类: 医药中间体 - 杂环化合物
• 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
• 中文名称: 7-硝基喹啉
• 英文名称: 7-nitroquinoline
• 英文别名: 7-Nitro-chinolin
• CAS: 613-51-4
• 化学式: C₉H₆N₂O₂
• mdl: MFCD00234498
• 分子量: 174.159
• InChiKey: MXKZSCXYMSXOAO-UHFFFAOYSA-N

物化性质

• 熔点：
  132.5°C
• 沸点：
  305.12°C (rough estimate)
• 密度：
  1.2190 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温和干燥环境

反应信息

• 作为反应物：
  描述：

  7-硝基喹啉 在 盐酸羟胺 、 肼 作用下， 以 乙醇 为溶剂， 生成 2,3-dimethyl-pyrido[2,3-f]quinoxaline
  参考文献：
  名称：

  Controlling Ground and Excited State Properties through Ligand Changes in Ruthenium Polypyridyl Complexes

  摘要：

  The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)(2)(N-N)](2+) (bpy = 2,2'-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the pi* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)(3)(2+) (lambda(max) = 449 nm) with the lowest energy MLCT absorption appearing at lambda(max) = 564 nm. Emission energies decrease from lambda(max) = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.

  DOI：

  10.1021/ic500408j
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 在 硫酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 7-硝基喹啉
  参考文献：
  名称：

  7-氨基喹啉及其衍生物的催化型激发态NH质子转移反应。

  摘要：

  已经对7-氨基喹啉（7AQ）及其各种氨基衍生物（-NHR）进行了战略设计和合成，以研究其激发态质子转移（ESPT）性能。由于质子供体-NHR和受体-N-之间的分离较大，因此如果存在7AQ衍生物中的ESPT，应在质子溶剂催化下进行。发现ESPT受-NHR的酸度和喹啉部分中质子受体-N-的碱性的影响。后者因-NHR取代基在喹啉-N-位点的共振效应而变化。对于那些经历了ESPT的7AQ衍生物，增加的喹啉碱度会导致更快的ESPT速率，这意味着从甲醇向喹啉部分提供质子可能是该过程的关键步骤。我们的研究还表明，就-NHR与甲醇的氢键（H键）构型而言，-NHR的顺式和反式排列之间存在平衡，因此只有顺式-H键形式经历了甲醇辅助的ESPT。除了一个例外，顺式和反式构型之间的相互转化比ESPT的速率快得多，产生具有明显弛豫动力学的氨基型（正常形式）和亚胺型（质子转移互变异构体）发射。

  DOI：

  10.1002/chem.201904027

文献信息

• Chemokine receptor binding heterocyclic compounds
  申请人：AnorMED, Inc.

  公开号：US06750348B1

  公开（公告）日：2004-06-15

  This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1 to R7 may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6 alkyl; R8 is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″ group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6 alkyl group, (3) a C0-6 alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6 alkylamino or C3-7 cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.

  这项发明涉及一类新型的杂环化合物，它们结合趋化因子受体，抑制其天然配体的结合。这些化合物通过结合趋化因子受体，包括CXCR4和CCR5，从而抑制这些趋化因子的后续结合，产生对HIV感染的保护效果。本发明提供了一个式I的化合物 其中，W是氮原子，Y不存在，或者W是碳原子，Y═H； R1至R7可以相同也可以不同，并且独立地选择自氢或直链、支链或环状的C1-6烷基； R8是一个取代的杂环基或取代的芳香基 Ar是一个芳香或杂芳环，每个环在单个或多个非连接位置可选择地取代有电子给体或吸引体基团； n和n′独立地为0-2； X是下式的一个基团： 其中，环A是一个可选择地取代的饱和或不饱和的5或6元环，P是一个可选择地取代的碳原子、一个可选择地取代的氮原子、硫或氧原子。环B是一个可选择地取代的5到7元环。上述式中的环A和环B可以通过基团V从任何位置连接到基团W，其中V是一个化学键，一个(CH2)n″基团（其中n″=0-2）或一个C═O基团。Z是(1)一个氢原子，(2)一个可选择地取代的C1-6烷基基团，(3)一个用可选择地取代的芳香或杂环基团取代的C0-6烷基基团，(4)一个可选择地取代的C0-6烷基氨基或C3-7环烷氨基基团，(5)一个可选择地取代的羰基或磺酰基。这些化合物还包括任何药学上可接受的酸盐和金属络合物，以及它们的任何立体异构体形式和立体异构体形式的混合物。
• Cu-Catalyzed Aerobic Oxidation of Di-<i>tert</i>-butyl Hydrazodicarboxylate to Di-<i>tert</i>-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions
  作者：Dahyeon Jung、Min Hye Kim、Jinho Kim

  DOI：10.1021/acs.orglett.6b03166

  日期：2016.12.16

  developed with homogeneous CuI and di-tert-butyl azodicarboxylate for aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines under mild conditions. The developed co-catalytic system is consisting of di-tert-butyl azodicarboxylate-mediated dehydrogenation of 1,2,3,4-tetrahydroquinoline and aerobic oxidative regeneration of di-tert-butyl azodicarboxylate from di-tert-butyl hydrazodicarboxylate using molecular

  用均相的CuI和偶氮二甲酸二叔丁酯开发了一种新型的共催化体系，用于在温和条件下对1,2,3,4-四氢喹啉进行好氧脱氢。发达共催化体系是由二-叔丁基偶氮二羧酸酯介导的二- 1,2,3,4-四氢喹啉和好氧氧化再生的脱氢叔丁基偶氮二羧酸酯选自二叔使用分子氧作为丁基hydrazodicarboxylate终端氧化剂。发达的铜和偶氮二羧酸二叔丁酯助催化体系有效地合成了各种喹啉。
• Monomeric vanadium oxide: a very efficient species for promoting aerobic oxidative dehydrogenation of N-heterocycles
  作者：Zhenbing Xie、Bingfeng Chen、Lirong Zheng、Fangfang Peng、Huizhen Liu、Buxing Han

  DOI：10.1039/d0nj04708b

  日期：——

  homogeneously in the catalysts. The VOx–NbOy@C catalysts displayed high performance in the aerobic oxidative dehydrogenation of N-heterocycles to aromatic heterocycles. It was demonstrated that the selectivity of reaction over the catalyst with a very small amount of V (0.07 wt%) was much higher than that over the NbOy@C, and the catalyst also exhibited excellent stability in the reaction. The detailed study

  单体活性物质在多相催化中非常有趣。在这项工作中，我们提出了一种制备VO x -NbO y @C催化剂的方法，该方法涉及一锅法水热合成含V / Nb的无机/有机杂化材料，然后在还原气氛下进行热处理。使用不同的技术对制备的催化剂进行表征，例如高角度环形暗场扫描透射电子显微镜和X射线吸收精细结构光谱学。结果表明，单体VO x物质均匀地分散在催化剂中。VO x –NbO y@C催化剂在N杂环好氧氧化脱氢成芳族杂环方面表现出高性能。结果表明，在极少量的V（0.07 wt％）的条件下，该催化剂的反应选择性比在NbO y C上的反应选择性高得多，该催化剂在反应中也表现出出色的稳定性。详细的研究表明，单体VO 2种类最能促进反应。
• Nucleophilic addition of amide anions to 1-methyl-5(6,7,8)-nitroquinolinium salts
  作者：Elena K. Avakyan、Gulminat А. Amangasieva、Oleg P. Demidov、Anastasia А. Borovleva、Elena S. Beketova、Oksana А. Nechaeva、Ivan V. Borovlev

  DOI：10.1007/s10593-019-02529-y

  日期：2019.8

  The stable adducts, N-(1-methyl-5(6,7,8)-nitro-1,2-dihydroquinolin-2-yl)benzamides were synthesized for the first time by the action of amide anions of aromatic acids on the N-methyl salts of 5-, 6-, 7-, and 8-nitroquinolines in anhydrous MeCN. Oxidative dehydrogenation of these amides afforded aroylimino derivatives of the corresponding 1-methyl-5(6,7,8)-nitro-2-quinolones.

  稳定的加合物N-（1-甲基-5（6,7,8）-硝基-1,2-二氢喹啉-2-基）苯甲酰胺是首次通过芳族酸的酰胺阴离子作用于其上而合成的。无水MeCN中5-，6-，7-和8-硝基喹啉的N-甲基盐。这些酰胺的氧化脱氢得到相应的1-甲基-5（6,7,8）-硝基-2-喹诺酮的芳香酰亚胺衍生物。
• [EN] TETRAHYDRONAPHTHYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE, AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE<br/>[FR] TÉTRAHYDRONAPHTYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE ET COMPOSÉS BICYCLIQUES APPARENTÉS POUR L'INHIBITION DE L'ACTIVITÉ DE RORGAMMA ET LE TRAITEMENT DE MALADIE
  申请人：MERCK SHARP & DOHME

  公开号：WO2015095795A1

  公开（公告）日：2015-06-25

  The invention provides certain bicylic heterocyclic compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein X1, X2, R1, R2, R3, R4, and Cy are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds of the Formula (I) or pharmaceutically acceptable salts thereof, and methods of using the compounds of the Formula (I) or pharmaceutically acceptable salts thereof or pharmaceutical compositions comprising the same for treating diseases or conditions mediated by RORgammaT.

  这项发明提供了公式（I）的某些双环杂环化合物或其药学上可接受的盐，其中X1、X2、R1、R2、R3、R4和Cy如本文所定义。该发明还提供了包括公式（I）的这种化合物或其药学上可接受的盐的药物组合物，以及使用公式（I）的这种化合物或其药学上可接受的盐或包含相同的药物组合物治疗由RORgammaT介导的疾病或症状的方法。

表征谱图