2-氰基-4-(吡咯烷-1-基)吡啶 | 127680-86-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氰基-4-(吡咯烷-1-基)吡啶
• 英文名称: 4-pyrrolidinopicolinonitrile
• 英文别名: 4-(Pyrrolidin-1-yl)pyridine-2-carbonitrile；4-pyrrolidin-1-ylpyridine-2-carbonitrile
• CAS: 127680-86-8
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: WHINRMKPWMUVEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  350.7±27.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

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: 4-(Pyrrolidin-1-yl)pyridine-2-carbonitrile
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-(Pyrrolidin-1-yl)pyridine-2-carbonitrile
CAS number: 127680-86-8

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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: C10H11N3
Molecular weight: 173.2

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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.

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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：

  2-氰基-4-(吡咯烷-1-基)吡啶 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 4.0h， 生成 N’-(piperidine-1-carbonothioyl)-4-(pyrrolidin-1-yl)picolinohydrazonamide
  参考文献：
  名称：

  4-取代的picolinooazonamides作为一类新的潜在抗结核药。

  摘要：

  合成了一系列新的4-取代的吡咯并酰肼酰胺（6-25），并评估了其抑菌活性。在硫代氨基脲链的末端具有亲水环胺的化合物，例如吗啉和吡咯烷，表现出最高的抗分枝杆菌活性。化合物6、11和15（MIC 0.4-0.8μg/ mL）的抗分枝杆菌活性高于参考药物。此外，衍生物15表现出对其他测试微生物如革兰氏阳性，革兰氏阴性或真菌的较低活性。因此，该化合物的特征在于抗微生物活性的选择性。针对人类皮肤成纤维细胞（HDF）和小鼠黑素瘤细胞系（B16-F10）进行的抗增殖研究表明，化合物15的细胞毒性较低。

  DOI：

  10.1016/j.ejmech.2020.112106
• 作为产物：
  描述：

  四氢吡咯 、 4-氯-2-氰基吡啶 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以90%的产率得到2-氰基-4-(吡咯烷-1-基)吡啶
  参考文献：
  名称：

  4-取代的picolinooazonamides作为一类新的潜在抗结核药。

  摘要：

  合成了一系列新的4-取代的吡咯并酰肼酰胺（6-25），并评估了其抑菌活性。在硫代氨基脲链的末端具有亲水环胺的化合物，例如吗啉和吡咯烷，表现出最高的抗分枝杆菌活性。化合物6、11和15（MIC 0.4-0.8μg/ mL）的抗分枝杆菌活性高于参考药物。此外，衍生物15表现出对其他测试微生物如革兰氏阳性，革兰氏阴性或真菌的较低活性。因此，该化合物的特征在于抗微生物活性的选择性。针对人类皮肤成纤维细胞（HDF）和小鼠黑素瘤细胞系（B16-F10）进行的抗增殖研究表明，化合物15的细胞毒性较低。

  DOI：

  10.1016/j.ejmech.2020.112106

文献信息

• A study of the photochemically induced reaction of pyridine-2,4-dicarbonitrile with primary and secondary amines. A direct synthesis of aminocyano-pyridines
  作者：Rosanna Bernardi、Tullio Caronna、Sergio Morrocchi、Maurizio Ursini、Bruno M. Vittimberga

  DOI：10.1039/p19900000097

  日期：——

  A novel synthesis of alkylaminopyridinecarbonitriles by a photoinitiated substitution reaction between pyridine-2,4-dicarbonitrile and certain amines is described. The mechanism is discussed.

  描述了通过吡啶-2，4-二甲腈和某些胺之间的光引发的取代反应的烷基氨基吡啶甲腈的新颖合成。讨论了该机制。
• Synthesis and Biological Activity of Piperidinothiosemicarbazones Derived from Aminoazinecarbonitriles
  作者：Dagmara Ziembicka、Katarzyna Gobis、Małgorzata Szczesio、Ewa Augustynowicz-Kopeć、Agnieszka Głogowska、Izabela Korona-Głowniak、Krzysztof Bojanowski

  DOI：10.3390/ph16091267

  日期：——

  significant activity against the standard strain (minimum inhibitory concentration (MIC) 2–4 μg/mL) and even greater activity against the resistant M. tuberculosis strain (MIC 0.5–4 μg/mL). Additionally, the effects of compounds 8–9 were entirely selective (MIC toward other microorganisms ≥ 1000 μg/mL) and non-toxic (IC50 to HaCaT cells 5.8 to >50 μg/mL). The antimycobacterial activity of pyrazine

  为了研究结构修饰如何影响结核抑制效力，我们合成了七种新的哌啶基缩氨基硫酮衍生物8-14，其中三个用吡嗪环取代了吡啶环。衍生物 8-9 和 13-14 对标准菌株表现出显着的活性（最低抑菌浓度 (MIC) 2-4 μg/mL），对耐药结核分枝杆菌菌株表现出更高的活性（MIC 0.5-4 μg/mL）。此外，化合物 8-9 的作用完全具有选择性（对其他微生物的 MIC ≥ 1000 μg/mL）且无毒（对 HaCaT 细胞的 IC50 5.8 至 >50 μg/mL）。吡嗪衍生物 11-12 的抗分枝杆菌活性可以忽略不计（MIC 256 至 >500 μg/mL），表明在这种情况下取​​代芳环通常不是一个有前途的研究方向。使用X射线晶体学测定化合物11的两性离子结构。吸收、分布、代谢和排泄 (ADME) 计算表明，除 11 种之外的所有化合物都可以考虑作为未来药物进行测试。对构效关系进行了分析
• Bernardi, Rosanna; Caronna, Tullio; Poggi, Gabriella, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 903 - 908
  作者：Bernardi, Rosanna、Caronna, Tullio、Poggi, Gabriella、Vittimberga, Bruno M.

  DOI：——

  日期：——
• BERNARDI, ROSANNA;CARONNA, TULLIO;MORROCCHI, SERGIO;URSINI, MAURIZIO;VITT+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 97-100
  作者：BERNARDI, ROSANNA、CARONNA, TULLIO、MORROCCHI, SERGIO、URSINI, MAURIZIO、VITT+

  DOI：——

  日期：——