1-氨基-2-氰基-1-环戊烯 | 2941-23-3

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-氨基-2-氰基-1-环戊烯
• 中文别名: 2-氨基-1-环戊烯-1-甲腈；2-氨基-1-环戊烯-1-腈
• 英文名称: 2-amino-1-cyanocyclopentene
• 英文别名: 2-aminocyclopent-1-enecarbonitrile；2-aminocyclopent-1-ene-1-carbonitrile；1-amino-2-cyano-1-cyclopentene；2-amino-1-cyclopentene-1-carbonitrile；2-aminocyclopentene-1-carbonitrile
• CAS: 2941-23-3
• 化学式: C₆H₈N₂
• mdl: MFCD00517551
• 分子量: 108.143
• InChiKey: NSMYBPIHVACKQG-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148℃
• 沸点：
  321.2±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xi
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P301+P312+P330,P304+P340+P311,P403+P233,P405,P501
• 危险品运输编号：
  3439
• 危险性描述：
  H331,H302
• 储存条件：
  应存放在2-8℃的环境中，保持干燥，避免光照，并在惰性气体氛围下保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-1-cyclopentene-1-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: 2-Amino-1-cyclopentene-1-carbonitrile
CAS number: 2941-23-3

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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, refrigerated.
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: C6H8N2
Molecular weight: 108.1

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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

制备方法与用途

用途

1-氨基-2-氰基-1-环戊烯是一种用于合成他克林-石杉碱甲杂合乙酰胆碱酯酶抑制剂的试剂。

反应信息

• 作为反应物：
  描述：

  1-氨基-2-氰基-1-环戊烯 在 lithium hydroxide 、 Mortierella isabellina NRRL 1757 、 硫酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (1R,2S)-1-methyl-2-hydroxy-1-cyclopentanecarbonitrile
  参考文献：
  名称：

  Preparation of Enantiopure Ketones and Alcohols Containing a Quaternary Stereocenter through Parallel Kinetic Resolution of β-Keto Nitriles

  摘要：

  Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kinetic-resolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

  DOI：

  10.1021/jo011092t
• 作为产物：
  描述：

  己二腈 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 15.0h， 以61%的产率得到1-氨基-2-氰基-1-环戊烯
  参考文献：
  名称：

  3D-QSAR药效团建模，虚拟筛选和对接研究，用于发现新型VEGFR 2抑制剂支架：设计，合成和生物学评估。

  摘要：

  成功设计，合成和评估了一系列新颖的6,7-二氢-5H-环戊[d]嘧啶衍生物，作为具有血管内皮生长因子受体（VEGFR 2）抑制活性的新型化学支架。化合物6c和6b在10 µM时分别显示97％和87％的酶抑制，并显示出有效的剂量相关VEGFR 2抑制，IC50值分别为0.85 µM和2.26 µM。6,7-二氢-5H-环戊[d]嘧啶骨架的设计是通过连续的分子建模方案进行的，然后进行衍生物的合成和生物学评估。首先，将索拉非尼停靠在VEGFR 2的结合位点以研究其结合方向和亲和力，然后生成有效的3D QSAR药效团模型，用于虚拟筛选不同的3D数据库。通过在VEGFR 2的结合位点进行分子对接研究，对具有前景的基于药效团的虚拟筛选结果的结构进行了改进。通过结合药效团模型生成和分子对接研究的结果，设计了一种新型支架。新的支架显示出与激酶前袋的疏水相互作用，这可能归因于在VEGFR 2中的停留时间增加

  DOI：

  10.1016/j.bioorg.2019.102988
• 作为试剂：
  描述：

  1,6-己二胺 、 光气 在 6-胺己腈 、 1-氨基-2-氰基-1-环戊烯 作用下， 420.0 ℃ 、90.0 kPa 条件下， 生成 1,6-己二异氰酸酯
  参考文献：
  名称：

  一种制备颜色稳定的1,6-己二异氰酸酯的方法

  摘要：

  本发明涉及一种制备颜色稳定的1,6-己二异氰酸酯的方法。该方法以低沸点组分，即四氢吖庚因、1-氨基-2-氰基-1-环戊烯和6-氨基己腈的含量≤50mg/kg的1,6-己二胺为原料，进行气相光气化反应，得到的1,6-己二异氰酸酯具有良好的颜色稳定性。

  公开号：

  CN103922969B

文献信息

• Diverse Tandem Cyclization Reactions of <i>o</i>-Cyanoanilines and Diaryliodonium Salts with Copper Catalyst for the Construction of Quinazolinimine and Acridine Scaffolds
  作者：Xinlong Pang、Chao Chen、Xiang Su、Ming Li、Lirong Wen

  DOI：10.1021/ol503156g

  日期：2014.12.5

  Two cyclization modes are realized to produce different nitrogen-containing heterocycles, i.e., quinazolin-4(3H)-imines and acridines by assembling o-cyanoanilines and diaryliodonium salts via tandem reaction pathways.

  通过经由串联反应途径组装邻氰基苯胺和二芳基碘鎓盐，实现了两种环化模式以产生不同的含氮杂环，即喹唑啉-4（3 H）-亚胺和a啶。
• Tin (IV) chloride-promoted reactions of β-dicarbonyl compounds with nitriles. Synthesis of aminopyridines and aminoquinolines.
  作者：Augusto C. Veronese、Rosella Callegari、Suada Ahmed Ali Salah

  DOI：10.1016/s0040-4039(00)97429-x

  日期：1990.1

  β-Ketoesters and β-diesters react with β-enaminonitriles in the presence of stoichiometric amounts of tin (IV) chloride to give 4-aminopyridines and pyridones while they react with aromatic orthoaminonitriles to give 4-aminoquinolines and quinolones.

  在化学计量的氯化锡（IV）存在下，β-酮酸酯和β-二酯与β-烯腈反应，生成4-氨基吡啶和吡啶酮，而与芳族邻氨基腈反应，生成4-氨基喹啉和喹诺酮。
• Niacin receptor agonists, compositions containing such compounds and methods of treatment
  申请人：Raghavan Subharekha

  公开号：US20060293364A1

  公开（公告）日：2006-12-28

  The present invention encompasses compounds of Formula I: as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating atherosclerosis, dyslipidemias and the like. Pharmaceutical compositions and methods of use are also included.

  本发明涵盖了Formula I的化合物： 以及其药用可接受的盐和水合物，用于治疗动脉粥样硬化、血脂异常等疾病。药物组合物和使用方法也包括在内。
• Radical Annulation of 2-Cyanoaryl Acrylamides via C═C Double Bond Cleavage: Access to Amino-Substituted 2-Quinolones
  作者：Wen-Jin Xia、Tai-Gang Fan、Zhi-Wei Zhao、Xin Chen、Xiang-Xiang Wang、Ya-Min Li

  DOI：10.1021/acs.orglett.1c02281

  日期：2021.8.6

  2-cyanoaryl acrylamides via C═C double bond cleavage has been developed for facile and efficient access to a broad spectrum of functionalized 4-amino-2-quinolones, which are important N-heterocycles. In this transformation, the solvent THF is demonstrated to play a crucial role, and the addition of alkyl radicals to nitrile, 1,5-hydride shift, and cleavage of the C–C bond are involved in the mechanism

  已经开发了一种通过 C=C 双键裂解的 2-氰基丙烯酰胺的新型环化，以方便有效地获得广泛的官能化 4-氨基-2-喹诺酮类化合物，它们是重要的N-杂环。在这种转化中，溶剂四氢呋喃被证明起着至关重要的作用，烷基与腈的加成、1,5-氢化物转移和 C-C 键的断裂都参与了该机制。
• Discovery of a series of ester-substituted NLRP3 inflammasome inhibitors
  作者：David Harrison、Nicolas Boutard、Krzysztof Brzozka、Marta Bugaj、Stefan Chmielewski、Anna Cierpich、John R. Doedens、Charles-Henry R.Y. Fabritius、Christopher A. Gabel、Michal Galezowski、Piotr Kowalczyk、Oleksandr Levenets、Magdalena Mroczkowska、Katarzyna Palica、Roderick A. Porter、David Schultz、Marta Sowinska、Grzegorz Topolnicki、Piotr Urbanski、Jakub Woyciechowski、Alan P. Watt

  DOI：10.1016/j.bmcl.2020.127560

  日期：2020.12

  the NLRP3 inflammasome have been approved. In this work, we used the known NLRP3 inflammasome inhibitor CP-456,773 (aka CRID3 or MCC 950) as our starting point and undertook a Structure-Activity Relationship (SAR) analysis and subsequent scaffold-hopping exercise. This resulted in the rational design of a series of novel ester-substituted urea compounds that are highly potent and selective NLRP3 inflammasome

  NLRP3 炎症小体是先天免疫系统的一个组成部分，参与促炎细胞因子的产生。各种外源性和内源性信号的异常激活可导致慢性、低度炎症。由于与大量未满足医疗需求的疾病有关，如阿尔茨海默病、帕金森病、关节炎和癌症，它作为药物靶点引起了极大的兴趣。迄今为止，尚未批准专门针对抑制 NLRP3 炎症小体的药物。在这项工作中，我们使用已知的 NLRP3 炎症小体抑制剂 CP-456,773（又名 CRID3 或 MCC 950）作为我们的起点，并进行了结构-活性关系 (SAR) 分析和随后的支架跳跃练习。44和45。据推测，酯部分充当高渗透性的递送载体，随后被羧酸酯酶水解为羧酸活性物质。这些分子与最先进的技术有很大不同，并在治疗 NLRP3 驱动的疾病方面提供了潜力，特别是在需要组织穿透的情况下。

表征谱图