1-(3-氟苯基)-2,5-二甲基吡咯 | 146135-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(3-氟苯基)-2,5-二甲基吡咯
• 英文名称: 1-(3-fluorophenyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: 1-(3-Fluorophenyl)-2,5-dimethylpyrrole
• CAS: 146135-21-9
• 化学式: C₁₂H₁₂FN
• mdl: MFCD07429171
• 分子量: 189.232
• InChiKey: WSZMMKRHLWEHTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(3-Fluorophenyl)-2,5-dimethylpyrrole
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: 1-(3-Fluorophenyl)-2,5-dimethylpyrrole
CAS number: 146135-21-9

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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: C12H12FN
Molecular weight: 189.2

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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, hydrogen fluoride.

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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：

  1-(3-氟苯基)-2,5-二甲基吡咯 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 5-[[1-(3-fluorophenyl)-2,5-dimethylpyrrol-3-yl]methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype

  摘要：

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.049
• 作为产物：
  描述：

  间氟硝基苯 、 2,5-己二酮 在 indium 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以87%的产率得到1-(3-氟苯基)-2,5-二甲基吡咯
  参考文献：
  名称：

  Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones

  摘要：

  One-pot reduction-triggered heterocyclizations of nitrobenzene derivatives with 1,4-diketones were investigated. In the presence of indium/AcOH in toluene at 80 degrees C, reaction of nitrobenzenes with 2,5-hexadione produced moderate to excellent yields (40-98%) of the corresponding pyrroles within 1.5-24 h depending on the substituents of the starting materials. Similarly, the reaction of nitrobenzenes with 1-phenyl-1,4-pantanedione in the presence of indium/AcOH in toluene at reflux afforded the corresponding pyrroles within 0.5-24 h with 60-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.113

文献信息

• Magnetic solid sulfonic acid-enabled direct catalytic production of biomass-derived <i>N</i>-substituted pyrroles
  作者：Keping Wang、Mei Wu、Yixuan Liu、Ying Yang、Hu Li

  DOI：10.1039/d1nj05828b

  日期：——

  Five-membered nitrogen heterocyclic pyrroles have extremely high physiological activity and are widely used in medicine, agriculture, materials chemistry, industry, and supramolecular chemistry. Developing a mild and eco-friendly way to synthesize functionalized pyrroles from biologically derived materials is desirable. In this study, biomass-derived 2,5-dimethylfuran can react with a series of aromatic

  五元氮杂环吡咯具有极高的生理活性，广泛应用于医药、农业、材料化学、工业、超分子化学等领域。开发一种温和且环保的方法来从生物衍生材料合成功能化吡咯是可取的。在这项研究中，生物质衍生的 2,5-二甲基呋喃可以与一系列芳香胺反应，通过酸开环和 Paal-Knorr 缩合在一个锅中合成 2,5-二甲基-N-芳基吡咯。在所测试的酸催化材料中，一种新型磁性生物碳基磺酸固体催化剂（WK-SO 3 H）在N-取代吡咯的合成中表现出优异的催化性能（最高可达约1.5%）。90% 收率），并且易于通过外部磁场分离和回收。呋喃的开环被证明是上述一锅多步转化过程的限速步骤，2,5-己二酮是级联反应的关键中间体，而水的加入可以显着提高反应速率。上述开环反应。此外，多种表征方法（例如FT-IR、TGA、XRD、NH 3 -TPD和XPS）证实WK-SO 3 H在水性反应体系中具有良好的稳定性。
• Pyrrole-thiazolidinone hybrids as a new structural class of broad-spectrum anti-infectives
  作者：Shujauddin Ahmed、Alka Mital、Abdul Akhir、Deepanshi Saxena、Mohammad Naiyaz Ahmad、Arunava Dasgupta、Sidharth Chopra、Rahul Jain

  DOI：10.1016/j.ejmech.2023.115757

  日期：2023.11

  pyrrole-thiazolidinone hybrids was designed, synthesized and evaluated for activities against ESKAP bacteria panel and mycobacterial pathogens. From the series, compound 9d showed prominent activity against S. aureus (MIC = 0.5 μg/mL) and compound 9k showed the most promising activity against M. tuberculosis H37Rv (MIC = 0.5 μg/mL). Potent derivatives were found to be non-toxic when tested against Vero cells.

  设计、合成了一系列吡咯-噻唑烷酮杂化物，并评估其针对 ESKAP 细菌组和分枝杆菌病原体的活性。在该系列中，化合物9d显示出显着的抗金黄色葡萄球菌活性。金黄色葡萄球菌(MIC = 0.5 μg/mL) 和化合物9k显示出最有希望的抗金黄色葡萄球菌活性。结核病H37Rv（MIC = 0.5 μg/mL）。当针对 Vero 细胞进行测试时，发现有效的衍生物是无毒的。化合物9d在针对几种MRSA和VRSA菌株的体外评估中产生了与标准药物相当或更好的活性。在抗生物膜测定中， 9d减少了S。在 10 倍 MIC 时，金黄色葡萄球菌生物膜增加 >11%。吡咯-噻唑烷酮杂化物表现出的双重抑制作用证实了它们作为新型有前途的抗感染剂的潜力。
• Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles
  作者：Elena Yu. Schmidt、Nadezhda V. Semenova、Elena V. Ivanova、Ivan A. Bidusenko、Boris A. Trofimov

  DOI：10.1016/j.mencom.2020.01.036

  日期：2020.1

  A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5-dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C=N bond of the intermediate aldimine (aza-Favorsky reaction).
• EBNA1 INHIBITORS AND THEIR METHOD OF USE
  申请人：The Wistar Institute Of Anatomy And Biology

  公开号：EP3068758A1

  公开（公告）日：2016-09-21
• [EN] EBNA1 INHIBITORS AND THEIR METHOD OF USE<br/>[FR] INHIBITEURS D'EBNA1 ET LEUR PROCÉDÉ D'UTILISATION
  申请人：WISAR INST OF ANATOMY AND BIOLOGY

  公开号：WO2015073864A1

  公开（公告）日：2015-05-21

  Pharmaceutical compositions of the invention comprise EBNA1 inhibitors useful for the treatment of diseases caused by EBNA1 activity such as cancer, infectious mononucleosis, chronic fatigue syndrome, multiple sclerosis, systemic lupus erythematosus and rheumatoid arthritis. Pharmaceutical compositions of the invention also comprise EBNA1 inhibitors useful for the treatment of diseases caused by latent Epstein-Barr Virus (EBV) infection. Pharmaceutical compositions of the invention also comprise EBNA1 inhibitors useful for the treatment of diseases caused by lytic Epstein-Barr Virus (EBV) infection.