6,7-二氢-5H-喹啉-8-酮 | 56826-69-8

• 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: 6,7-二氢-5H-喹啉-8-酮
• 中文别名: 6,7-二氢-5H-8-喹啉酮；6,7-二氢喹啉-8(5H)-酮
• 英文名称: 5,6,7,8-Tetrahydroquinolin-8-one
• 英文别名: 5,6,7,8-tetrahydro-8-quinolinone；6,7-dihydroquinolin-8(5H)-one；6,7-dihydro-5H-quinolin-8-one；5,6,7-trihydroquinolin-8-one
• CAS: 56826-69-8
• 化学式: C₉H₉NO
• mdl: MFCD03839916
• 分子量: 147.177
• InChiKey: JIAKIQWNYAZUJD-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  140 °C(Press: 0.1 Torr)
• 密度：
  1.168±0.06 g/cm3(Predicted)
• 溶解度：
  DMF: 30 mg/ml,DMSO: 30 mg/ml,乙醇: 30 mg/ml,PBS (pH 7.2): 10 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

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：
  H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6,7-Dihydro-5H-quinolin-8-one
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 6,7-Dihydro-5H-quinolin-8-one
CAS number: 56826-69-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H9NO
Molecular weight: 147.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6,7-二氢-5H-喹啉-8-酮 在 盐酸羟胺 、 potassium acetate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 6,7-二氢-5H-吡啶并[2,3-b]氮杂革-8(9H)-酮
  参考文献：
  名称：

  [EN] FABI INHIBITORS FOR GRAM-NEGATIVE PATHOGENS
  [FR] INHIBITEURS DE FABI POUR DES PATHOGÈNES À GRAM NÉGATIF

  摘要：

  一种名为Fabimycin的FabI抑制剂对200多种临床分离的E. coli、K. pneumoniae和A. baumannii表现出令人印象深刻的活性。Fabimycin在多个小鼠感染模型中对革兰氏阴性菌引起的感染具有活性，包括尿路感染模型。Fabimycin具有翻译前景，其发现提供了数据，表明其谱系活性仅限于革兰氏阳性菌的抗生素可以被系统地改变以在革兰氏阴性菌中积累并对这些问题菌产生作用。

  公开号：

  WO2022187329A1
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉 在 草酰氯 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.33h， 生成 6,7-二氢-5H-喹啉-8-酮
  参考文献：
  名称：

  高效的 Pyrazolo[5,4-f]quinoxaline 功能化 Os(II) 基发射体，在 811 nm 处具有最大电致发光峰值

  摘要：

  具有功能性吡唑并[3,4- f ]喹喔啉螯合物的Os(II)配合物实现了高效但几乎“不可见”的近红外电致发光，峰值最大。超过 800 纳米。

  DOI：

  10.1002/chem.202103202
• 作为试剂：
  描述：

  5,6,7,8-四氢-8-氨基喹啉 在 6,7-二氢-5H-喹啉-8-酮 、 4 A molecular sieve 、 immobilized Candida antarctica Lipase B 、 水 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (8R)-5,6,7,8-四氢-8-氨基喹啉
  参考文献：
  名称：

  8-氨基-5,6,7,8-四氢喹啉的自发酶促动力学动力学拆分

  摘要：

  在南极假丝酵母脂肪酶B存在的情况下，观察到了8-氨基-5,6,7,8-四氢喹啉1的自发动态动力学拆分，其中（R）-乙酰胺[（R）-2]的收率> 60％从外消旋胺中分离出]。酮3的自发形成，然后通过烯胺4与其余（S）-胺1的缩合/水解过程提供了必要的消旋途径。

  DOI：

  10.1021/jo062037t

文献信息

• An air and moisture tolerant iminotrihydroquinoline-ruthenium(<scp>ii</scp>) catalyst for the transfer hydrogenation of ketones
  作者：Jiaoyan Li、Yingmiao Ma、Zheng Wang、Qingbin Liu、Gregory A. Solan、Yanping Ma、Wen-Hua Sun

  DOI：10.1039/c8dt01919c

  日期：——

  with RuCl2(PPh3)3 at room temperature affords the ruthenium(II) chelate (8-NH2-C9H10N)RuCl2(PPh3)2 (E), in which the two triphenylphosphine ligands are disposed mutually cis. By contrast, when the reaction is performed at reflux ligand oxidation/dehydrogenation occurs along with cis–trans reorganization of the triphenylphosphines to form the 8-imino-5,6,7-trihydroquinoline-ruthenium(II) complex, (8

  8-氨基-5,6,7,8-四氢喹啉在室温下与RuCl 2（PPh 3）3反应得到钌（II）螯合物（8-NH 2 -C 9 H 10 N）RuCl 2（PPh 3）2（E），其中两个三苯基膦配体相互顺式排列。相反，当反应在回流条件下进行时，配体会发生氧化/脱氢以及三苯基膦的顺式-反式重组，形成8-亚氨基-5,6,7-三氢喹啉-钌（II）络合物，（8-NH C9 H 9 N）RuCl 2（PPh 3） 2（ F）。通过单独加热E溶液至回流，也可以高收率获得配合物F。它们的分子结构比较突出了F中的二齿亚胺配体比E中的含胺对应物优越的结合性能。两种络合物在多种烷基-，芳基-和环烷基的酮的转移氢化中非常有效，从而提供其相应的仲醇，其负载量低至0.1 mol％。明显地， F即使在与空气接触的反应釜中，即使是台式质量的2-丙醇也可以提供出色的转化率，而E的催化效率会因空气的存在而降低，但只能在惰性条件下有效地操作。
• Electrochemical benzylic oxidation of C–H bonds
  作者：Jason A. Marko、Anthony Durgham、Stacey Lowery Bretz、Wei Liu

  DOI：10.1039/c8cc08768g

  日期：——

  An electrochemical benzylic C–H oxidation reaction that is mediated by tert-butyl peroxyl radical is reported.

  一种由叔丁基过氧自由基介导的芳基C-H氧化反应被报道。
• [EN] SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE<br/>[FR] INHIBITEURS À PETITE MOLÉCULE DE KINASE INDUISANT NF-KB
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2020239999A1

  公开（公告）日：2020-12-03

  The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

  本发明涉及抑制NIK的化合物，以及包含这些化合物的药物组合物和使用方法。这些化合物和药物组合物预期能用于预防或治疗癌症（如包括白血病、淋巴瘤和多发性骨髓瘤的B细胞恶性肿瘤）、炎症性疾病、自身免疫疾病、免疫皮肤病学疾病（如掌跖脓疱病和化脓性汗腺炎）以及代谢紊乱疾病（如肥胖和糖尿病）。
• Rigid geometry 8-arylimino-7,7-dimethyl-5,6-dihydroquinolyl nickel bromides: single-site active species towards ethylene polymerization
  作者：Chuanbing Huang、Youfu Zhang、Tongling Liang、Zhijuan Zhao、Xinquan Hu、Wen-Hua Sun

  DOI：10.1039/c6nj02464e

  日期：——

  to probe the solid state structures of L1, L3 and Ni1–Ni4; this technique provided valuable information regarding the net charge on nickel within the complexes. Upon activation with either methylaluminoxane (MAO) or ethylaluminium sesquichloride (EASC), all nickel complexes exhibited high activities towards ethylene polymerization and produced polyethylene waxes with low molecular weights. The catalytic

  制备了稠环杂环酮5,6-二氢-7,7-二甲基喹啉-8-one，并用于合成一系列8-芳基-7,7-二甲基-5,6-二氢喹啉衍生物（芳基= 2,6-Me 2 Ph（L1），2,6-Et 2 Ph（L2），2,4,6-Me 3 Ph（L3），2,6-Et 2 -4-MePh（L4） ，2,6-i-Pr 2 Ph（L5））。的反应L1-L4与（DME）NIBR 2（DME = 1,2-二甲氧基乙烷），得到相应的阳离子双-螯合物，[（Lx的）2 NIBR] [BR]（Lx的= L1（Ni1），L2（Ni2），L3（Ni3），L4（Ni4）），为溴化物盐；没有这样的复合物可以用体积最大的L5分离出来。所有新化合物均使用IR光谱，元素分析进行​​表征，对于L1 - L5则使用1 H和13 C NMR光谱进行表征。此外，Ni1和Ni3的分子结构已经确定，并且它们揭示了基于三角双锥体锥体含镍阳离子电荷并由溴
• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。

表征谱图