4-羟基-6-甲基喹啉 | 23432-40-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 4-羟基-6-甲基喹啉
• 英文名称: 6-methylquinolin-4-ol
• 英文别名: 6-methyl-1H-quinolin-4-one
• CAS: 23432-40-8
• 化学式: C₁₀H₉NO
• mdl: MFCD12192791
• 分子量: 159.188
• InChiKey: PJEUKNUOCWNERE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• WGK Germany：
  3
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  存放在室温、干燥密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Hydroxy-6-methylquinoline
Product Name:
Synonyms: 6-Methylquinolin-4-ol

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H318: Causes serious eye damage
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Hydroxy-6-methylquinoline
CAS number: 23432-40-8

---

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.

---

Section 7. Handling and storage
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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.
Storage: Store in closed vessels.

---

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.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
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.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-羟基-6-甲基喹啉 在 ammonium hydroxide 、 三氯氧磷 作用下， 生成 4-氯-6-甲基喹啉
  参考文献：
  名称：

  关于双电荷四氮杂环烷作为小电导Ca 2+激活的K +通道的强抑制剂的进一步研究

  摘要：

  以前，已证明基于喹啉鎓的四氮杂环烷酮（例如UCL 1684和UCL 1848）作为有效的小肽非肽类阻滞剂，对化学结构的变化（尤其是对环庚烷体系的大小）非常敏感。电导Ca 2+激活的K +离子通道（SK Ca）。当前的工作试图优化UCL 1848中连接链的结构。我们报道了29个UCL 1848类似物的合成和SK Ca通道阻滞活性，其中UCL 1848的中心CH 2被其他基团X或取代。 Y = O，S，CF 2，C O，CHOH，C C，CHCH，CHMe，以探索键长或柔韧性的细微变化是否可以进一步提高效力。通过合成和测试带有取代基（NO 2，NH 2，CF 3，F，Cl，CH 3，OCH 3，OCF 3， OH）在氨基喹啉鎓环的5、6或7个位置上。与我们之前的工作一样，测定了每种化合物对大鼠交感神经元后超极化（AHP）的抑制作用，这种作用是由SK Ca通道的SK3亚型介导的。一种新化合物（39，R

  DOI：

  10.1016/j.ejmech.2013.02.029
• 作为产物：
  描述：

  4-methyl-2-(trimethylsilylethynyl)aniline 在 盐酸 、 copper(l) iodide 、 十六烷基三甲基溴化铵 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 30.0h， 生成 4-羟基-6-甲基喹啉
  参考文献：
  名称：

  铜催化的2-异氰基乙酰苯的化学选择性环化反应：合成4-羟基喹啉化合物。

  摘要：

  描述了铜催化的2-异氰基苯乙酮衍生物的分子内环化反应，以化学方式提供4-羟基喹啉。该转化通过烯醇互变异构和随后的CC键形成而进行。与以前的方法相比，本研究为在温和条件下从官能化异氰酸酯构建4-羟基喹啉化合物提供了新的方法。

  DOI：

  10.1021/acs.joc.9b02903

文献信息

• A visible-light-irradiated electron donor-acceptor complex-promoted radical reaction system for the C H perfluoroalkylation of quinolin-4-ols
  作者：Yunze Li、Min Rao、Zhenwei Fan、Baoyi Nian、Yaofeng Yuan、Jiajia Cheng

  DOI：10.1016/j.tetlet.2019.151046

  日期：2019.9

  An efficient method for visible-light-induced perfluoroalkylaion of quinolin-4-ol has been reported. In the presence of t-BuONa and perfluoroalkyl iodide, quinolin-4-ol underwent CH perfluoroalkylation under the irradiation of green light. Mechanistic studies demonstrated that visible-light promoted intermolecular charge transfer within the transient electron donor-acceptor complex in the absence of

  已经报道了可见光诱导的喹啉-4-醇全氟烷基阴离子的有效方法。在t- BuONa和全氟烷基碘的存在下，喹啉-4-醇在绿光照射下经历了C H全氟烷基化。机理研究表明，在没有任何光催化剂的情况下，可见光促进了瞬态电子供体-受体复合物中分子间的电荷转移。
• Quinoline derivatives having anti-tumor activity
  申请人：Imperial Chemical Industries PLC

  公开号：US05112837A1

  公开（公告）日：1992-05-12

  The invention relates to a quinoline of the formula: ##STR1## wherein each of R.sup.1 and R.sup.2, which may be the same or different, is hydrogen, halogeno, hydroxy, cyano, carbamoyl, nitro or amino, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkanoylamino each of up to 4 carbon atoms, or substituted alkyl or alkoxy each of up to 3 carbon atoms, provided that both R.sup.1 and R.sup.2 are not hydrogen; the quinoline ring may bear further substituents; R.sup.3 is hydrogen or alkyl of up to 4 carbon atoms; R.sup.4 is hydrogen, alkyl, alkenyl or alkynyl each of up to 4 carbon atoms or substituted alkyl of up to 3 carbon atoms; Ar is phenylene, naphthylene or heterocyclene which is unsubstituted or which bears one or more substituents; R.sup.5 is such that R.sup.5 --NH.sub.2 is an amino acid; or a pharmaceutically-acceptable salt or ester thereof. The compounds possess anti-tumor activity.

  本发明涉及一种喹啉，其公式为：##STR1## 其中，R.sup.1和R.sup.2可以是相同的或不同的，为氢、卤素、羟基、氰基、碳酰胺基、硝基或氨基，为碳原子数不超过4的烷基、烷氧基、烷硫基、烷氨基、二烷氨基或烷酮氨基，或为碳原子数不超过3的取代烷基或取代烷氧基，但R.sup.1和R.sup.2均不为氢；喹啉环可带有进一步的取代基；R.sup.3为氢或碳原子数不超过4的烷基；R.sup.4为氢、碳原子数不超过4的烷基、烯基或炔基，或为碳原子数不超过3的取代烷基；Ar为二价苯基、二价萘基或杂环基，其中未取代或带有1个或多个取代基；R.sup.5满足R.sup.5 --NH.sub.2是一种氨基酸；或其药用可接受的盐或酯。这些化合物具有抗肿瘤活性。
• Compounds and Methods of Treatment
  申请人：LACKEY Karen Elizabeth

  公开号：US20080234267A1

  公开（公告）日：2008-09-25

  A derivative, which is useful as a ret kinase inhibitor is described herein. The described invention also includes methods of using the same in the treatment of diseases mediated by inappropriate ret kinase activity.

  本文描述了一种作为Ret酪氨酸激酶抑制剂有用的衍生物。所述发明还包括使用相同物质治疗由不当的Ret酪氨酸激酶活性介导的疾病的方法。
• Synthesis of Bridged Benzazocines and Benzoxocines by a Titanium-Catalyzed Double-Reductive Umpolung Strategy
  作者：Plamen Bichovski、Thomas M. Haas、Daniel Kratzert、Jan Streuff

  DOI：10.1002/chem.201405852

  日期：2015.2.2

  A sequence of two titanium(III)‐catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo‐ and benzoxozine building blocks. The first step is a reductive cross‐coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn‐selectivity for the quinolone functionalization while the anti‐diastereomers are obtained as the major

  据报道，由两个钛（III）催化的还原性蛋白还原反应序列可快速构建苯并偶氮和苯并恶嗪结构单元。第一步是喹诺酮或色酮与迈克尔受体的还原性交叉偶联。这种反应完全进行SYN -选择性的喹诺酮类功能化，而抗-diastereomers是从色酮的主要产品获得。在不同的反应条件下，可以改变立体化学结果以提供合成苯并二氢吡喃酮产品。随后的还原性酮基自由基环化以良好的产率锻造了三环标题化合物。提供了解释所观察到的立体选择性的立体化学模型，并且通过X射线分析和2D NMR光谱实验明确验证了产物构型。
• Bicyclic Kinase Inhibitors
  申请人：Burger Matthew

  公开号：US20110195980A1

  公开（公告）日：2011-08-11

  New compounds, compositions and methods of inhibition of Provirus Integration of Maloney Kinase (PIM kinase) activity associated with tumorigenesis in a human or animal subject are provided. In certain embodiments, the compounds and compositions are effective to inhibit the activity of at least one PIM kinase. The new compounds and compositions may be used either alone or in combination with at least one additional agent for the treatment of a serine/threonine kinase- or receptor tyrosine kinase-mediated disorder, such as cancer.

  提供了用于抑制与人类或动物主体中的肿瘤发生相关的PIM激酶（PIM kinase）活性的新化合物、组合物和抑制方法。在某些实施例中，这些化合物和组合物能够有效抑制至少一种PIM激酶的活性。这些新化合物和组合物可以单独使用，也可以与至少一种额外药物联合使用，用于治疗丝氨酸/苏氨酸激酶或受体酪氨酸激酶介导的疾病，如癌症。