3-溴-5-硝基喹啉 | 116632-33-8

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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: 3-溴-5-硝基喹啉
• 英文名称: 3-bromo-5-nitroquinoline
• CAS: 116632-33-8
• 化学式: C₉H₅BrN₂O₂
• 分子量: 253.055
• InChiKey: VBGNJJXCTAWOIU-UHFFFAOYSA-N

物化性质

• 熔点：
  203-205 °C
• 沸点：
  325.0±0.0 °C(Predicted)
• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在室温、干燥且密封的环境中。

反应信息

• 作为反应物：
  描述：

  3-溴-5-硝基喹啉 在 硫酸 、 palladium diacetate 、 铁粉 、 potassium carbonate 、 氯化铵 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium nitrite 作用下， 以 2-甲基四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 ethyl 5-((dimethylcarbamoyl)oxy)quinoline-3-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

  摘要：

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.

  DOI：

  10.1021/acs.joc.5b01119
• 作为产物：
  描述：

  5-硝基喹啉 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 以100%的产率得到3-溴-5-硝基喹啉
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

  摘要：

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.

  DOI：

  10.1021/acs.joc.5b01119

文献信息

• [EN] SPIRO-FUSED TRICYCLIC MAP4K1 INHIBITORS<br/>[FR] INHIBITEURS DE MAP4K1 TRICYCLIQUES SPIRO FUSIONNÉS
  申请人：BAYER AG

  公开号：WO2021074279A1

  公开（公告）日：2021-04-22

  The present invention relates to Map4K1 inhibitors of formula (I) to pharmaceutical compositions and combinations comprising the compounds according to the invention, and to the prophylactic and therapeutic use of the inventive compounds, respectively to the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular for neoplastic disorders, repectively cancer or conditions with dysregulated immune responses or other disorders associated with aberrant MAP4K1 signaling, as a sole agent or in combination with other active ingredients. The present invention further relates to the use, respectively to the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of protein inhibitors in benign hyperplasias, atherosclerotic disorders, sepsis, autoimmune disorders, vascular disorders, viral infections, in neurodegenerative disorders, in inflammatory disorders, in atherosclerotic disorders and in male fertility control.

  本发明涉及式(I)的MAP4K1抑制剂，以及包含根据本发明的化合物的药物组合物和组合物，以及创新化合物的预防性和治疗性用途，分别用于制造用于治疗或预防疾病的药物组合物，特别是用于肿瘤性疾病，癌症或与异常MAP4K1信号相关的其他紊乱免疫反应或其他紊乱的疾病，作为单一药剂或与其他活性成分组合使用。本发明还涉及使用，分别用于制造用于治疗或预防良性增生、动脉粥样硬化疾病、败血症、自身免疫疾病、血管疾病、病毒感染、神经退行性疾病、炎症性疾病、动脉粥样硬化疾病和男性生育控制的蛋白抑制剂的药物组合物的用途。
• Tetraazaarenes by the ceramidonine approach
  作者：Parantap Sarkar、Ie-Rang Jeon、Fabien Durola、Harald Bock

  DOI：10.1039/c2nj21033a

  日期：——

  The synthesis of extended heteroarenesvia the acid-promoted dehydrocyclisation of arylamino-anthraquinones is examined as an approach to highly conjugated electron-acceptor materials and eventually to heterographene nanoribbons. Whilst the latter perspective is found to remain challenging, the former is exemplified by the synthesis of extended tetraazaheterocycles bearing solubilising alkyl substituents.

  通过酸催化的脱环化反应合成扩展的杂芳烃，被作为一种高共轭电子受体材料的途径，最终导向异石墨烯纳米带。尽管后者的视角仍被认为具有挑战性，但前者的例子则是合成带有溶解性烷基取代基的扩展四氮杂环。
• Enantioselective transfer hydrogenation, a key step for the synthesis of 3-aminotetrahydroquinolines
  作者：Alexandre Aillerie、Vincent Lemau de Talencé、Clément Dumont、Sylvain Pellegrini、Frédéric Capet、Till Bousquet、Lydie Pélinski

  DOI：10.1039/c6nj02249a

  日期：——

  An enantioselective transfer hydrogenation has been successfully achieved to furnish 3-aminotetrahydroquinolines. The reaction was conducted in the presence of Hantzsch dihydropyridine and a catalytic amount of chiral phosphoric acid under mild conditions.

  已经成功实现对映选择性转移氢化，以提供3-氨基四氢喹啉。反应在温和条件下在汉兹二氢吡啶和催化量的手性磷酸的存在下进行。
• Protonmotive Force: Development of Electrostatic Drivers for Synthetic Molecular Motors
  作者：James D. Crowley、Ian M. Steele、Brice Bosnich

  DOI：10.1002/chem.200500519

  日期：2006.12.4

  Ferrocene has been investigated as a platform for developing protonmotive electrostatic drivers for molecular motors. When two 3-pyridine groups are substituted to the (rapidly rotating) cyclopentadienyl (Cp) rings of ferrocene, one on each Cp, it is shown that the (Cp) eclipsed, pi-stacked rotameric conformation is preferred both in solution and in the solid state. Upon quaternization of both of the

  二茂铁已被研究为开发用于分子电动机的质子静电驱动器的平台。当两个3-吡啶基团被取代到二茂铁的（快速旋转的）环戊二烯基（Cp）环上时，每个Cp上都显示出（Cp）黯淡，π堆积的旋转异构构象，无论是在溶液中还是在溶液中都是优选的固体状态。当两个吡啶取代基通过质子化或烷基化进行季铵化时，表明优选的旋转异构构象是其中吡啶鎓基团旋转远离完全π-堆积构象的构象。静电计算表明旋转是由电荷之间的静电排斥引起的。一致地，当pi堆叠能量增加时，pi堆叠人口增加，相反，当静电排斥力增加时，π堆积的人口就会减少。这项工作旨在提供对静电驱动的二茂铁平台结合到分子电动机中时可以产生的扭矩大小的近似估计。总的结论是，二价二茂铁二吡啶基系统之间的静电相互作用能类似于pi堆积相互作用能，因此，至少需要三阳离子体系才能完全解开pi堆积吡啶取代基。
• Regiodivergent Synthesis of 11 <i>H</i> ‐Indolo[3,2‐ <i>c</i> ]quinolines and Neocryptolepine from a Common Starting Material
  作者：Katja S. Håheim、Bjarte Aarmo Lund、Magne O. Sydnes

  DOI：10.1002/ejoc.202300137

  日期：——

  A common intermediate gives easy access to both neocryptolepine and isocryptolepine analogues in up to 80 % and 95 % yield, respectively.

  一种常见的中间体可以很容易地以高达 80% 和 95% 的收率分别获得新隐藤碱和异隐藤碱类似物。