4-羟基-6-甲氧基喹啉-2-酮 | 14300-45-9

• 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-甲氧基喹啉-2-酮
• 中文别名: 2,4-二羟基-6-甲氧基喹啉
• 英文名称: 4-hydroxy-6-methoxy-1H-quinolin-2-one
• 英文别名: 4-hydroxy-6-methoxyquinolin-2(1H)-one；4-Hydroxy-6-methoxy-carbostyril；2,4-Dihydroxy-6-methoxyquinoline
• CAS: 14300-45-9
• 化学式: C₁₀H₉NO₃
• mdl: MFCD01463812
• 分子量: 191.186
• InChiKey: HBHIHNYMVBNMOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 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：
  58.6
• 氢给体数：
  2
• 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：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2,4-Dihydroxy-6-methoxyquinoline
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2,4-Dihydroxy-6-methoxyquinoline
CAS number: 14300-45-9

---

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.

---

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.

---

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
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:

---

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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H9NO3
Molecular weight: 191.2

---

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.

---

Section 12. Ecological information
No data.

---

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-甲氧基喹啉-2-酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 19.5h， 生成 haplamine
  参考文献：
  名称：

  (4+2)环加成反应合成吡喃喹啉生物碱

  摘要：

  通过生成邻醌甲基化物中间体和多聚甲醛，分别从 4-羟基喹啉 2 (l//)-酮、二甲基丙烯酸和多聚甲醛合成吡喃喹啉类生物碱，如弗林德辛、单丙胺、1-V-甲基弗林德辛及其衍生物。进行 (4+2) 环加成。此外，二氢中间体被 DDQ 氧化。简介 吡喃喹啉是芸香科植物许多生物碱的主要组成单位，因其有趣的药理特性而倍受重视”。Flindersine 4a 是吡喃喹啉生物碱家族的成员，是从弗林德西亚的木材中分离出来的australis 于 1984 年。 O-Quinone methide 是有机合成中的重要中间体，它们的作用是 1, 3-氧杂丁二烯单元在逆电子需求 Diels-Alder 反应中得到了广泛的研究”。然而，一般杂环醌甲基化物，特别是喹诺酮醌甲基化物的 Diels-Alder 反应很少受到关注”。在本文中，我们编写了一种新的直接方法，用于合成吡喃喹啉类生物碱，如 Findersine、

  DOI：

  10.1515/hc.2005.11.1.79
• 作为产物：
  描述：

  N,N'-bis(4-methoxyphenyl)malonamide 在 PPA 作用下， 反应 16.0h， 以85%的产率得到4-羟基-6-甲氧基喹啉-2-酮
  参考文献：
  名称：

  芸香科异戊二烯基，呋喃基和吡喃基喹啉生物碱的简便合成方法

  摘要：

  描述了一种方便的合成4-羟基-3-异戊烯基-2-喹诺酮的方法，该方法被认为是芸香科异戊二烯基，呋喃基和吡喃喹啉生物碱的前体。该方法涉及2，4-二羟基喹啉的C，C-二烯丙基化，然后使用碲化氢钠试剂进行部分脱甲酰化。

  DOI：

  10.1016/0040-4020(89)80106-1

文献信息

• Mild, Efficient and Selective Silver Carbonate Mediated O-Alkylation of 4-Hydroxy-2-quinolones: Synthesis of 2,4-Dialkoxyquinolines
  作者：Enrique L. Larghi、Ademir Farias Morel、Marcel Manke Selvero

  DOI：10.1055/s-2005-918945

  日期：——

  The reaction of 4-hydroxy-2-quinolones with alkyl iodides, benzyl bromides and allyl bromides in benzene at room temperature, in the presence of Ag 2 CO 3 , afforded 2,4-dialkoxyquinolines in moderate to excellent yields. The process is highly regioselective and constitutes a new and mild one-pot alternative for the preparation of this class of compounds.

  4-羟基-2-喹诺酮类与烷基碘、苄基溴和烯丙基溴在室温下在苯中，在Ag 2 CO 3 存在下反应，以中等至极好的收率得到2,4-二烷氧基喹啉。该方法具有高度区域选择性，构成了制备此类化合物的一种新的、温和的单锅替代方法。
• A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups
  作者：Rajasekar Reddy Annapureddy、Christian Jandl、Thorsten Bach

  DOI：10.1021/jacs.0c02803

  日期：2020.4.22

  of various quinolones and pyridones. The C-H activation reaction proceeded with high site- and enantioselectivity (14 examples, 83-97% ee). Key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahy-dro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol%) served as the silver source, PhI=NNs as the nitrene precursor and 1,10- phenanthroline

  据报道，在各种喹诺酮类和吡啶酮类的脂肪族 C3 取代基上发生了银催化的胺化。CH 活化反应以高位点和对映选择性进行（14 个实例，83-97% ee）。其成功的关键是使用手性菲咯啉配体，该配体通过乙炔基接头连接到八氢-1H-4,7-methanoisoindol-1-one 的 8 位。AgPF6 (10 mol%) 作为银源，PhI=NNs 作为氮烯前体，1,10-菲咯啉作为配体。反应结果可以通过假设在氢键银络合物中插入氮烯 CH 来理解，其中单个 CH 键暴露于催化反应中心。
• Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity
  作者：Mohammed A. I. Elbastawesy、Yaseen A. M. M. El-Shaier、Mohamed Ramadan、Alan B. Brown、Ashraf A. Aly、Gamal El-Din A. Abuo-Rahma

  DOI：10.1007/s11030-019-10021-0

  日期：2021.2

  A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09 µM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00 µM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye® software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors.

  一系列6-取代的喹啉-2-酮硫脲6a–j已被合成。目标化合物的结构通过不同的光谱和元素分析得到证实。所有设计的最终化合物分别对产生脲酶的R. mucilaginosa和Proteus mirabilis细菌作为真菌和细菌病原体的体外活性进行了评估。此外，所有化合物在体外采用杯盘扩散法作为潜在的脲酶抑制剂进行了测试。化合物6a和6b活性最强，分别为（IC50 = 0.58 ± 0.15和0.43 ± 0.09μM），与先导化合物I（IC50 = 1.13 ± 0.00μM）相比。此外，设计的化合物通过Open Eye®软件对接入脲酶蛋白（ID：3LA4和ID：4UBP），以正确理解配体-受体相互作用。对接结果显示，设计的化合物可以通过多个强氢键与酶的活性位点相互作用。此外，还描述了化学结构的快速叠加分析，以理解合成的化合物作为脲酶抑制剂的3D QSAR。结果强调了直接连接到6-取代喹诺酮部分的极性硫脲作为有前途的抗菌脲酶抑制剂的重要性。
• New Quinoline-2-one/thiazolium bromide Derivatives; Synthesis, Characterization and Mechanism of Formation
  作者：Sara M. Mostafa、Ashraf A. Aly、Samia M. Sayed、Mohamed A. Raslan、Amira E. Ahmed、Ayman Nafady、Esam A. Ishak、Ahmed M. Shawky、El-Shimaa M.N. Abdelhafez

  DOI：10.1016/j.molstruc.2021.130501

  日期：2021.9

  We report on the formation of new quinoline-2-one derived by thiazolium bromides from the reaction of 3-thiosemicarbazides derived by 2-quinolones with 2-bromoacetophenones. The structure of products was elucidated by mass, IR and NMR spectra together with elemental analysis. The mechanism of products formation was discussed.

  我们报道了由噻唑溴化物衍生的新喹啉-2-酮的形成，该喹啉-2-酮是由2-喹诺酮与2-溴苯乙酮衍生的3-硫代氨基脲的反应。通过质量，IR和NMR光谱以及元素分析来阐明产物的结构。讨论了产品形成的机理。
• Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives
  作者：Ashraf A. Aly、Asmaa H. Mohamed、Mohamed Ramadan

  DOI：10.1016/j.molstruc.2020.127798

  日期：2020.5

  Abstract We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized

  摘要 我们指导了 1,6,7-三取代-4-苯基噻唑-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one 衍生物的合成，通过 2-quinolone 衍生物衍生的相应缩氨基硫脲与 2 -溴苯乙酮在室温下三乙胺存在下。讨论了形成产物的机理。使用不同的光谱技术，包括红外 (IR)、核磁共振 (NMR) 和质谱 (MS) 以及元素分析，对所得产物的结构进行了全面表征。新合成的化合物显示出中等的结肠抗癌活性。