5-甲氧基喹啉 | 6931-19-7

• 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: 5-甲氧基喹啉
• 英文名称: 5-methoxyquinoline
• CAS: 6931-19-7
• 化学式: C₁₀H₉NO
• mdl: MFCD02752664
• 分子量: 159.188
• InChiKey: ZFVRPAOFSPXEIM-UHFFFAOYSA-N

物化性质

• 沸点：
  282 °C(Press: 758 Torr)
• 密度：
  1.130±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.1
• 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：
  P280
• 危险性描述：
  H302,H315
• 储存条件：
  应存于阴凉避光处，并置于惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methoxyquinoline
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: 5-Methoxyquinoline
CAS number: 6931-19-7

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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.
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: C10H9NO
Molecular weight: 159.2

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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：

  5-甲氧基喹啉 在 platinum(IV) oxide 氢气 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -78.0 ℃ 、413.68 kPa 条件下， 生成 1,2,3,4-四氢喹啉-5-醇
  参考文献：
  名称：

  Synthesis and SAR of novel histamine H3 receptor antagonists

  摘要：

  The synthesis and biological evaluation of novel tetrahydroisoquinoline, tetrahydroquinoline, and tetrahydroazepine antagonists of the human and rat H-3 receptors are described. The substitution around these rings as well as the nature of the substituent on nitrogen is explored. Several compounds with high affinity and selectivity for the human and rat H-3 receptors are reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.004
• 作为产物：
  描述：

  5-氨基喹啉 在 硫酸 、 sodium hydride 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 5-甲氧基喹啉
  参考文献：
  名称：

  신규 퀴놀린 화합물 및 이를 포함하는 암의 예방 또는 치료용 약학 조성물

  摘要：

  本发明涉及一种对癌细胞具有优异抑制增殖作用的喹诺啉化合物，其药学上可接受的盐或水合物，以及其制备方法和用作抗癌疾病预防或治疗的药物组合物，该化合物、其药学上可接受的盐或水合物根据本发明具有优异的抗癌细胞抑制活性和蛋白激酶及突变激酶的抑制活性，因此可以作为副作用较少的新型抗癌药物得到有益应用。

  公开号：

  KR101778938B1

文献信息

• Cu-Catalyzed carbamoylation<i>versus</i>amination of quinoline<i>N</i>-oxide with formamides
  作者：Yan Zhang、Shiwei Zhang、Guangxing Xu、Min Li、Chunlei Tang、Weizheng Fan

  DOI：10.1039/c8ob02844c

  日期：——

  An efficient, direct carbamoylation and amination of quinoline N-oxides with formamides to access 2-carbamoyl and 2-amino quinolines has been developed through copper-catalyzed C–C and C–N bond formations via cross-dehydrogenative coupling reactions. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. Mechanistic studies suggest

  通过铜催化的C-C和C-N键的形成，通过交叉脱氢偶联反应，已开发出一种高效，直接的氨基甲酰基化和喹啉N-氧化物与甲酰胺的胺化反应，以生成2-氨基甲酰基和2-氨基喹啉。在温和条件下，该反应可在广泛的具有良好官能团耐受性的底物上顺利进行。机理研究表明，根据甲酰胺N原子上不同的取代基，在TBHP存在下，该反应是由甲酰胺基或脱羰基氨酰基自由基的形成引发的。
• Homogeneous pressure hydrogenation of quinolines effected by a bench-stable tungsten-based pre-catalyst
  作者：Thomas Vielhaber、Christian Heizinger、Christoph Topf

  DOI：10.1016/j.jcat.2021.10.020

  日期：2021.12

  on an operationally simple catalytic method for the tungsten-catalyzed hydrogenation of quinolines through the use of the easily handled and self-contained precursor [WCl(η5-Cp)(CO)3]. This half sandwich complex is indefinitely storable on the bench in simple screw-capped bottles or stoppered flasks and can, if required, be prepared on a multi-gram scale while the actual catalytic transformations were

  我们报告了一种操作简单的催化方法，通过使用易于处理且自给自足的前体 [WCl(η 5 -Cp)(CO) 3 ] ，用于喹啉的钨催化氢化。这种半夹心复合物可以无限期地储存在简单的螺旋盖瓶或塞瓶中的工作台上，如果需要，可以在多克规模上制备，同时在 路易斯酸的存在下进行实际的催化转化，以便实现良好的底物转化率和产品产量。所描述的方法代表了对各种 1,2,3,4-四氢喹啉的简便和原子效率的访问，从而避免了成本密集型和氧敏感性膦配体以及辅助氢化物试剂的使用。
• Copper(<scp>ii</scp>)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines
  作者：Gang Li、Chunqi Jia、Kai Sun、Yunhe Lv、Feng Zhao、Kexiao Zhou、Hankui Wu

  DOI：10.1039/c5ob00135h

  日期：——

  Copper acetate-catalyzed C–H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields.

  使用醋酸铜催化的C-H键官能团化氨基化反应实现了喹啉N-氧化物的转化，以O-苯甲酰羟胺作为亲电氨基化试剂，从而以中等至优异的产率获得了所需的产品。

• N-Heterocycle-Triggered MCRs: An Approach to the Concise Synthesis of Perfluoroalkylated Spiro-1,3-oxazines
  作者：Hui Zhang、Weiguo Cao、Gang Liu、Yueci Wu、Jing Han、Weimin He、Jie Chen、Hongmei Deng、Min Shao

  DOI：10.1055/s-0037-1609563

  日期：2018.12

  affording the products in good to excellent yields. Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl- or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded

  摘要 在靛红和二芳基1,2-二酮的存在下，由N-杂环（喹啉，异喹啉和苯并噻唑）引发的涉及全氟烷-2-酸甲酯的多组分反应可有效地获得三氟甲基或其他全氟烷基取代的螺-1,3 -恶嗪衍生物。这种简便的转化具有区域选择性，并在温和的条件下顺利通过1，4-偶极中间体进行转化，从而使产品收率良好至优异。 在靛红和二芳基1,2-二酮的存在下，由N-杂环（喹啉，异喹啉和苯并噻唑）引发的涉及全氟烷-2-酸甲酯的多组分反应可有效地获得三氟甲基或其他全氟烷基取代的螺-1,3 -恶嗪衍生物。这种简便的转化具有区域选择性，并在温和的条件下顺利通过1，4-偶极中间体进行转化，从而使产品收率良好至优异。
• Metal‐ and Solvent‐Free, One‐Pot Synthesis of 3‐Unsubstituted Benzoindolizines
  作者：Lukas Schifferer、Olga García Mancheño

  DOI：10.1002/ejoc.202001245

  日期：2020.12.13

  A simple, one‐pot, metal‐free method for the synthesis of 3‐unsubstituted indolizines from readily available (iso)quinolines and propiolates is presented. Employing solvent‐free conditions, the competitive cyclization into 1,2‐disubstituted indolizines was suppressed, allowing remarkable chemoselectivity towards the synthetically valuable C1 mono‐substituted indolizines.

  提出了一种简单，单罐，无金属的方法，该方法可从容易获得的（异）喹啉和丙酸酯合成3-未取代的吲哚嗪。在无溶剂条件下，竞争性环化成1,2-二取代的吲哚嗪类化合物被抑制，从而对具有合成价值的C1单取代的吲哚嗪类化合物具有显着的化学选择性。

表征谱图