4-氯-8-甲基喹唑啉 | 58421-80-0

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4-氯-8-甲基喹唑啉
• 英文名称: 4-chloro-8-methylquinazoline
• CAS: 58421-80-0
• 化学式: C₉H₇ClN₂
• mdl: MFCD08457971
• 分子量: 178.621
• InChiKey: UTBDPFFXKANFFT-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  298.2±20.0 °C(Predicted)
• 密度：
  1.292

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Chloro-8-methylquinazoline
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: 4-Chloro-8-methylquinazoline
CAS number: 58421-80-0

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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: C9H7ClN2
Molecular weight: 178.6

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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, hydrogen chloride.

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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：

  4-氯-8-甲基喹唑啉 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 11.0h， 生成 (1E,4E)-1-(3,4-dichlorophenyl)-5-(2-(8-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  新型（1 E，4 E）-1-芳基-5-（2-（喹唑啉-4-基氧基）苯基）-1,4-戊二烯-3-酮衍生物的合成及抗病毒活性

  摘要：

  通过取代醛与苯甲醛的反应合成了一系列新颖的（1 E，4 E）-1-芳基-5- [2-（喹唑啉-4-基氧基）苯基] -1,4-戊二烯-3-酮衍生物。中间体4a – f。抗病毒生物测定表明，大多数化合物在500μg/ mL的浓度下对烟草花叶病毒（TMV）和黄瓜花叶病毒（CMV）表现出有希望的离体抗病毒生物活性。还讨论了结构与抗病毒活性之间的关系。化合物5a，6e和6g在离体TMV上可具有大约50％的明显保护性生物活性（EC 50）分别为257.7、320.7和243.3μg/ mL。该研究首次证明（1 E，4 E）-1-芳基-5-（2-（喹唑啉-4-基氧基）苯基）-1,4-戊二烯-3-酮可用于开发潜力植物用杀病毒剂。

  DOI：

  10.1016/j.ejmech.2013.02.035
• 作为产物：
  描述：

  2-氨基-3-甲基苯甲酸甲酯 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-氯-8-甲基喹唑啉
  参考文献：
  名称：

  含二硫缩醛部分的新型喹唑啉衍生物的合成，抗病毒活性和诱导的耐药机制

  摘要：

  设计并合成了一系列含有二硫缩醛部分的新型喹唑啉衍生物，并通过1 H核磁共振，13 C核磁共振和高分辨率质谱对它们的结构进行了表征。生物测定结果表明，化合物4b对黄瓜花叶病毒（CMV，EC 50  = 248.6μg/ mL）表现出显着的保护活性，对马铃薯病毒Y（EC 50  = 350.5μg/ mL）的治疗活性，优于宁南霉素（CMV，EC 50 = 350.5μg/ mL）。分别为357.7μg/ mL和493.7μg/ mL）。此外，化合物4b 可以增加植物中的叶绿素含量，改善光合作用，并有效诱导烟草抗CMV活性。

  DOI：

  10.1016/j.bioorg.2018.06.026

文献信息

• [EN] NEW SOMATOSTATIN RECEPTOR SUBTYPE 4 (SSTR4) AGONISTS<br/>[FR] NOUVEAUX AGONISTES DU RÉCEPTEUR DE SOMATOSTATINE DE SOUS-TYPE 4 (SSTR4)
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014184275A1

  公开（公告）日：2014-11-20

  The invention relates to 3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide derivatives of general formula (I), which are agonists of somatostatin receptor subtype 4 (SSTR4), useful for preventing or treating medical disorders related to SSTR4. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture of the compounds according to the invention.

  这项发明涉及一般式(I)的3-aza-双环[3.1.0]己烷-6-羧酸酰胺衍生物，它们是生长抑素受体亚型4（SSTR4）的激动剂，用于预防或治疗与SSTR4相关的医学疾病。此外，该发明涉及制备药物组合物的方法，以及根据该发明制备化合物的方法。
• [EN] ARYL AND HETEROARYL-FUSED TETRAHYDRO-1,4-OXAZEPINE AMIDES AS SOMATOSTATIN RECEPTOR SUBTYPE 4 (SSTR4) AGONISTS<br/>[FR] TÉTRAHYDRO-1,4-OXAZÉPINE AMIDES FUSIONNÉES PAR ARYLE ET HÉTÉROARYLE EN TANT QU'AGONISTES DU RÉCEPTEUR DE LA SOMATOSTATINE DE SOUS-TYPE 4 (SSTR4)
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2016075239A1

  公开（公告）日：2016-05-19

  The invention relates to aryl and heteroaryl-fused tetrahydro-1,4-oxazepine amide derivatives of general formula (l),which are agonists of somatostatin receptor subtype 4 (SSTR4), useful for preventing or treating medical disorders related to SSTR4. In addition, the invention relates processes for manufacture of the compounds according to the invention.

  这项发明涉及一般式(l)的芳基和杂环芳基融合的四氢-1,4-噁唑啉酰胺衍生物，这些衍生物是生长抑素受体亚型4（SSTR4）的激动剂，可用于预防或治疗与SSTR4相关的医学疾病。此外，该发明涉及根据该发明制造化合物的工艺。
• Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes
  作者：Jiajia Ma、Shuming Chen、Peter Bellotti、Renyu Guo、Felix Schäfer、Arne Heusler、Xiaolong Zhang、Constantin Daniliuc、M. Kevin Brown、Kendall N. Houk、Frank Glorius

  DOI：10.1126/science.abg0720

  日期：2021.3.26

  highly regio- and diastereoselective intermolecular [4 + 2] dearomative cycloaddition reaction of these bicyclic azaarenes with a plethora of electronically diverse alkenes. This approach bypasses the general reactivity and selectivity issues, thereby providing various bridged polycycles that previously have been inaccessible or required elaborate synthetic efforts. Computational studies with density

  脱芳环加成反应是将平面芳烃转化为三维结构的理想方法，这在药物化学中日益受到关注。喹啉、异喹啉和喹唑啉尽管含有潜在的二烯和烯烃亚基，但由于芳族体系固有的低反应性和选择性挑战，很少应用于环加成反应。在这里，我们公开了这些双环氮杂芳烃与大量电子不同的烯烃的能量转移介导的、高度区域和非对映选择性的分子间[4 + 2]脱芳香环加成反应。这种方法绕过了一般的反应性和选择性问题，从而提供了以前无法获得或需要精心合成的各种桥连多环。密度泛函理论的计算研究阐明了观察到的区域选择性和非对映选择性的机制和起源。
• [EN] POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS<br/>[FR] ANTAGONISTES DE TLR7/8 POLYCYLIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES IMMUNES
  申请人：MERCK PATENT GMBH

  公开号：WO2017106607A1

  公开（公告）日：2017-06-22

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

  本发明涉及式(I)的化合物及其药学上可接受的组合物，作为Toll样受体7/8（TLR7/8）拮抗剂。在式(I)中，环A是芳基或杂芳基；环B是芳基或杂芳基；X是C(R4)2、O、NR4、S、S(R4)或S(R4)2。
• Antibacterial activity of quinoxalines, quinazolines, and 1,5-naphthyridines
  作者：Ajit K. Parhi、Yongzheng Zhang、Kurt W. Saionz、Padmanava Pradhan、Malvika Kaul、Kalkal Trivedi、Daniel S. Pilch、Edmond J. LaVoie

  DOI：10.1016/j.bmcl.2013.06.048

  日期：2013.9

  Several phenyl substituted naphthalenes and isoquinolines have been identified as antibacterial agents that inhibit FtsZ-Zing formation. In the present study we evaluated the antibacterial of several phenyl substituted quinoxalines, quinazolines and 1,5-naphthyridines against methicillin-sensitive and methicillin-resistant Staphylococcus aureus and vancomycin-sensitive and vancomycin-resistant Enterococcus

  几种苯基取代的萘和异喹啉已被鉴定为抑制 FtsZ-Zing 形成的抗菌剂。在本研究中，我们评估了几种苯基取代的喹喔啉、喹唑啉和 1,5-萘啶对甲氧西林敏感和耐甲氧西林金 黄色葡萄球菌和万古霉素敏感和耐万古霉素的粪 肠球菌的抗菌作用。一些对金黄色葡萄球菌更有效的化合物评估了它们对 FtsZ 蛋白质聚合的影响。还进行了进一步的研究以评估它们的相对杀菌和抑菌活性。在非季铵化和季铵化喹喔啉衍生物之间观察到的显着差异表明，不同的作用机制与其抗菌特性有关。