6-苯基-苯并咪唑并[1,2- C]喹啉 | 28381-92-2

• 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: 6-苯基-苯并咪唑并[1,2- C]喹啉
• 中文别名: 6-苯基-苯并咪唑并[1,2-C]喹啉
• 英文名称: 6-phenylbenzimidazolo<1,2-c>quinazoline
• 英文别名: 6-phenylbenzimidazo<1,2-c>quinazoline；6-phenylbenzo[4,5]imidazo[1,2-c]quinazoline；6-phenylbenzimidazole[1,2-c]quinazoline；6-phenylbenzimidazo[1,2-c]quinazoline；6-phenyl-benzo[4,5]imidazo[1,2-c]quinazoline；6-phenyl-benz[4,5]imidazo[1,2-c]quinazoline；6-phenylbenzimidazolo[1,2-c]quinazoline
• CAS: 28381-92-2
• 化学式: C₂₀H₁₃N₃
• 分子量: 295.343
• InChiKey: CJXRQYFQNGCDJA-UHFFFAOYSA-N

物化性质

• 熔点：
  231-233 °C(Solv: ethanol (64-17-5); ligroine (8032-32-4))
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Phenyl-benzimidazol(1,2-c)quinazoline
9-Phenyl-8,10,17-triazatetracyclo[8.7.0.0{ˆ2,7}.0{ˆ11,16}]heptadeca-1(17),2(7),3,5,8,11,13,15-octaene
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-Phenyl-benzimidazol(1,2-c)quinazoline
CAS number: 28381-92-2

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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: C20H13N3
Molecular weight: 295.3

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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：

  iridium(III) acetylacetonate 、 6-苯基-苯并咪唑并[1,2- C]喹啉 以 乙醇 为溶剂， 反应 30.0h， 以70%的产率得到
  参考文献：
  名称：

  TWI520958

  摘要：

  公开号：
• 作为产物：
  描述：

  N-苯基苄脒 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 碘苯二乙酸 、 zinc diacetate 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 6-苯基-苯并咪唑并[1,2- C]喹啉
  参考文献：
  名称：

  Rhodium(III)-catalyzed [4 + 2] annulation of N-arylbenzamidines with 1,4,2-dioxazol-5-ones: Easy access to 4-aminoquinazolines via highly selective C H bond activation

  摘要：

  DOI：

  10.1016/j.cclet.2021.02.061

文献信息

• Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
  作者：Shan Xu、Juyou Lu、Hua Fu

  DOI：10.1039/c1cc10383k

  日期：——

  A convenient and efficient copper-catalyzed cascade method has been developed for the synthesis of benzimidazoquinazoline derivatives via reactions of readily available substituted 2-(2-halophenyl)benzoimidazoles with amidines or guanidine under mild conditions (even at room temperature).

  已经开发了一种方便有效的铜催化级联方法，用于在温和的条件下（即使在室温下）通过容易获得的取代的2-（2-卤代苯基）苯并咪唑与am或胍的反应来合成苯并咪唑并喹唑啉衍生物。
• Rh-Catalyzed Annulation of <i>ortho</i> -C−H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-<i>c</i> ]quinazolines
  作者：Xiaopeng Wu、Song Sun、Shengbo Xu、Jiang Cheng

  DOI：10.1002/adsc.201701331

  日期：2018.3.20

  A Rh‐catalyzed unique and direct approach for constructing a series of 5‐arylimidazo[1,2‐c]quinazolines in moderate to excellent yields from simple and readily available 2‐arylimidazoles and 3‐phenyl‐1,4,2‐dioxazol‐5‐ones was described. This procedure proceeds with sequential ortho‐C−H bond amidation and cyclization, which represents a facile and straightforward pathway to access such frameworks.

  用Rh催化的独特直接方法从简单易得的2芳基咪唑和3苯基-1,4,2-二恶唑-以中等到优异的收率构建一系列5芳基咪唑[1,2- c ]喹唑啉描述了5分。此过程以顺序的邻-C-H键酰胺化和环化进行，这代表了访问此类框架的便捷途径。
• General and efficient copper-catalyzed aerobic oxidative synthesis of N-fused heterocycles using amino acids as the nitrogen source
  作者：Qing Liu、Haijun Yang、Yuyang Jiang、Yufen Zhao、Hua Fu

  DOI：10.1039/c3ra41644e

  日期：——

  efficient copper-catalyzed aerobic oxidative method for the synthesis of N-fused heterocycles has been developed by using readily available α-amino acids as the nitrogen source. The reactions underwent N-arylation, aerobic oxidative dehydrogenation, intramolecular cyclization and dissociation of formic acid. This method should provide a general and practical strategy for the construction of N-fused

  通过使用容易获得的α-氨基酸作为氮源，已经开发了用于合成N-稠合杂环的通用且有效的铜催化的需氧氧化方法。反应进行了N-芳基化，好氧氧化脱氢，分子内环化和C的解离甲酸。该方法应为构建N-稠合杂环提供通用和实用的策略。
• Design, synthesis and antifungal activity evaluation of isocryptolepine derivatives
  作者：Jun-cai Li、Ren-xuan Wang、Yu Sun、Jia-kai Zhu、Guan-fang Hu、Yu-ling Wang、Rui Zhou、Zhong-min Zhao、Ying-qian Liu、Jing-wen Peng、Yin-fang Yan、Xiao-fei Shang

  DOI：10.1016/j.bioorg.2019.103266

  日期：2019.11

  2-c] quinazoline. A series of “Aza”-type derivatives were designed, synthesized and evaluated for their antifungal activity against six plant fungi in vitro. Among all derivatives, compounds A-0, B-1 and B-2 showed significant antifungal activity against B. cinerea with the EC50 values of 2.72 μg/mL, 5.90 μg/mL and 4.00 μg/mL, respectively. Compound A-2 had the highest activity against M. oryzae with

  在本文中，将氮原子插入异隐油环的蒽环系统中，以获得“ Aza”型结构的苯并[4,5]咪唑并[1,2-c]喹唑啉。设计，合成了一系列“ Aza”型衍生物，并对其在体外对六种植物真菌的抗真菌活性进行了评估。在所有衍生物中，化合物A-0，B-1和B-2对灰葡萄孢具有显着的抗真菌活性，EC 50值分别为2.72μg/ mL，5.90μg/ mL和4.00μg/ mL。化合物A-2对米曲霉的活性最高，其EC 50值为8.81μg/ mL，A-1表现出对最防治效果纹枯病菌（EC 50，6.27微克/毫升）。此外，选择了化合物A-0来研究针对灰葡萄孢菌的体内测试，结果表明，在100μg/ mL浓度下，化合物的预防效果高达72.80％。初步的机理研究表明，用5 µg / mL的A-0处理后，灰葡萄孢菌的菌丝体出现弯曲，塌陷，并且细胞膜的完整性可能会受损。改变了菌丝的活性氧产生，线粒体膜电位和核形态，破坏了
• Copper-Catalyzed Sequential Ullmann <i>N</i>-Arylation and Aerobic Oxidative C–H Amination: A Convenient Route to Indolo[1,2-<i>c</i>]quinazoline Derivatives
  作者：Peng Sang、Yongju Xie、Jianwei Zou、Yuhong Zhang

  DOI：10.1021/ol3016435

  日期：2012.8.3

  An efficient synthesis of indolo[1,2-c]quinazoline derivatives has been developed by copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C–H amination. The protocol uses readily available 2-(2-halophenyl)-1H-indoles and (aryl)methanamines as the starting materials to afford indolo[1,2-c]quinazolines, which are the core units of hinckdentine A.

  通过铜催化的顺序Ullmann N-芳基化反应和好氧氧化CH-H胺化反应，已开发出吲哚[1,2- c ]喹唑啉衍生物的有效合成方法。该协议使用容易获得的2-（2-卤代苯基）-1 H-吲哚和（芳基）甲胺作为起始原料来提供吲哚并[1,2- c ]喹唑啉，它们是hinckdentine A的核心单元。