5-氨基-4-氰基-1-苯基-1H-吡唑-3-甲酸乙酯 | 93764-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-4-氰基-1-苯基-1H-吡唑-3-甲酸乙酯
• 英文名称: ethyl 5-amino-4-cyano-1-phenyl-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 5-amino-4-cyano-1-phenylpyrazole-3-carboxylate
• CAS: 93764-93-3
• 化学式: C₁₃H₁₂N₄O₂
• 分子量: 256.264
• InChiKey: IEBFWSOLRJKQQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 5-amino-4-cyano-1-phenylpyrazole-3-carboxylate
Synonyms: Ethyl 5-amino-4-cyano-1-phenyl-1H-pyrazole-3-carboxylate

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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: Ethyl 5-amino-4-cyano-1-phenylpyrazole-3-carboxylate
CAS number: 93764-93-3

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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: C13H12N4O2
Molecular weight: 256.3

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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：

  5-氨基-4-氰基-1-苯基-1H-吡唑-3-甲酸乙酯 在 硫酸 作用下， 以85%的产率得到ethyl 5-amino-4-carbamoyl-1-phenyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  5-氨基-4-氰基-1-苯基-1H-吡唑-3-羧酸乙酯的新合成和反应

  摘要：

  合成5-氨基-4-氰基-1-苯基-1- ħ吡唑-3-甲酸乙酯5已经通过的异常贝克曼重排实现ö -chloroaldehyde 1。的反应ø -aminocarbonitrile 5与浓硫酸2 SO 4家具的预期ö -aminocarboxamide吡唑6。关键中间体邻氨基甲腈5和邻氨基羧酰胺6被成功地用于合成吡唑并嘧啶衍生物。邻氯乙腈中Cl的替代3与仲胺一起提供了新的合成子13，该合成子进一步用于合成多取代的杂环。所获得的新产物通过IR，1 H和13 C NMR以及质谱进行了很好的表征。

  DOI：

  10.1002/jhet.1691
• 作为产物：
  描述：

  ethyl 5-chloro-4-formyl-1-phenyl-1H-pyrazole-3-carboxylate 在 吡啶 、 氯化亚砜 、 sodium azide 、 sodium dithionite 、 盐酸羟胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.0h， 生成 5-氨基-4-氰基-1-苯基-1H-吡唑-3-甲酸乙酯
  参考文献：
  名称：

  5-氨基-4-氰基-1-苯基-1H-吡唑-3-羧酸乙酯的新合成和反应

  摘要：

  合成5-氨基-4-氰基-1-苯基-1- ħ吡唑-3-甲酸乙酯5已经通过的异常贝克曼重排实现ö -chloroaldehyde 1。的反应ø -aminocarbonitrile 5与浓硫酸2 SO 4家具的预期ö -aminocarboxamide吡唑6。关键中间体邻氨基甲腈5和邻氨基羧酰胺6被成功地用于合成吡唑并嘧啶衍生物。邻氯乙腈中Cl的替代3与仲胺一起提供了新的合成子13，该合成子进一步用于合成多取代的杂环。所获得的新产物通过IR，1 H和13 C NMR以及质谱进行了很好的表征。

  DOI：

  10.1002/jhet.1691

文献信息

• Substituted Pyrazoles as Ghrelin Receptor Antagonists
  申请人：Ge Min

  公开号：US20090253673A1

  公开（公告）日：2009-10-08

  Certain novel N-acylated spiropiperidine derivatives are ligands of the human ghrelin receptor(s) and, in particular, are antagonists/inverse agonists of the human ghrelin receptor. They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of the ghrelin receptor, such as obesity, diabetes, and metabolic syndrome.

  某些新型N-酰化螺环哌啶衍生物是人类胃饥素受体的配体，特别是人类胃饥素受体的拮抗剂/逆向激动剂。因此，它们对于治疗、控制或预防对胃饥素受体调节敏感的疾病和疾病是有用的，如肥胖症、糖尿病和代谢综合征。
• New heterocyclic syntheses from hydrazidoyl halides. Convenient syntheses of fused pyrimidines, pyridazines, and quinazolines
  作者：Abdou O. Abdehamid、Cyril PÁrkÁnyi、Ahmad S. Shawali、Magda A. Abdalla

  DOI：10.1002/jhet.5570210425

  日期：1984.7

  Aminocyanopyrazole derivatives and pyrazolo[2,3-a]quinazolones were obtained in good yields from hydrazidoyl halides and malononitrile. Pyrazolo[3,4-d]pyridazine and pyridazo[4′,5′: 1,2]pyrazolo[1,5-a]quinazoline derivatives were synthesized in quantitative yields by reaction of hydrazine hydrate with 2 and 16, respectively. A novel ring system, a 3-substituted tetrahydro derivative of 7-oxo-6H,8H-pyridazo[3′

  氨基氰基吡唑衍生物和吡唑并[2，3- a ]喹唑酮类从酰肼基卤化物和丙二腈中以良好的产率获得。通过水合肼与2和16的反应分别定量合成吡唑并[3,4- d ]哒嗪和哒唑并[4'，5'：1,2，]吡唑并[1,5- a ]喹唑啉衍生物。制备了一种新型的环体系，即7-氧代-6 H，8 H-吡啶唑[ 3'，4'，5'- c'd' ]-吡唑并[3,4- d ]嘧啶的3-取代四氢衍生物。通过6与碳酸二甲酯的反应。吡唑啉[3,4- d通过2与二硫化碳反应以高收率获得]嘧啶-4，6-二硫酮。根据产品的元素分析，光谱数据和可能的合成方法，对产品的结构进行分配和确认。方案1总结了本工作中讨论的母体稠合杂环系统的结构。
• Palladium and Copper Cocatalyzed Intermolecular Cyclization Reaction: Synthesis of 5-Aminopyrazole Derivatives
  作者：Chaowei Ma、Ping Wen、Jihui Li、Xu Han、Zhaoyang Wu、Guosheng Huang

  DOI：10.1002/adsc.201500767

  日期：2016.3.31

  A novel and efficient palladium and copper co‐catalyzed intermolecular cyclization of acetonitriles with hydrazones has been developed for the synthesis of 5‐aminopyrazoles through CC and CN bond formation. The reaction has the advantages of easily available starting materials, simple manipulation and mild reaction conditions. The reaction involving various substituted acetonitriles and hydrazones

  已开发出一种新颖且有效的钯和铜与共催化的乙腈分子间环化反应，用于通过C CC和CN键的形成合成5-氨基吡唑。该反应具有容易获得的起始原料，简单的操作和温和的反应条件的优点。涉及各种取代乙腈和的反应进行得很顺利，并且以高收率合成了5-氨基吡唑。与脂族和杂芳族底物相反，芳族底物倾向于具有更高的反应性。
• Synthesis, Cannabinoid Receptor Affinity, and Molecular Modeling Studies of Substituted 1-Aryl-5-(1<i>H</i>-pyrrol-1-yl)-1<i>H</i>-pyrazole-3-carboxamides
  作者：Romano Silvestri、Maria Grazia Cascio、Giuseppe La Regina、Francesco Piscitelli、Antonio Lavecchia、Antonella Brizzi、Serena Pasquini、Maurizio Botta、Ettore Novellino、Vincenzo Di Marzo、Federico Corelli

  DOI：10.1021/jm070566z

  日期：2008.3.1

  The new 1-phenyl-5-(1H-pyrrol-1-yl)pyrazole-3-carboxamides were compared with the reference compounds AM251 and SR144528 for cannabinoid hCB(1) and hCB(2) receptor affinity. Compounds bearing 2,4-dichlorophenyl or 2,4-difluorophenyl groups at position 1 and 2,5-dimethylpyrrole moiety at position 5 of the pyrazole nucleus were generally more selective for hCB(1). On the other hand, the N-cyclohexyl group at the 3-carboxamide was the determinant for the hCB2 selectivity, in particular when a 3,4-dichlorophenyl group was also present at position 1. Compound 26 was the most selective ligand for the hCB(1) receptor (K-i (CB2)/K-i (CB1) = 140.7). Derivative 30, the most potent hCB(1) ligand (Ki = 5.6 nM), was equipotent to AM251 and behaved as an inverse agonist in the cAMP assay (EC50 similar to 1 nM). The carbonyl oxygen of both 26 and 30 formed a H-bond with K3.28(192), while the substituents at the nitrogen fitted in a pocket formed by lipophilic residues. This H-bonding interaction was proposed to account for the high affinity for receptors' inactive state and the inverse agonist activity.
• Abdelhamid, Abdou O., Journal of Chemical Research, Miniprint, 1993, # 6, p. 1239 - 1262
  作者：Abdelhamid, Abdou O.

  DOI：——

  日期：——