(6,7,8,9-四氢-5H-[1,2,4]噻唑并[4,3-a]氮杂革-3-基)-乙腈 | 116598-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 中文名称: (6,7,8,9-四氢-5H-[1,2,4]噻唑并[4,3-a]氮杂革-3-基)-乙腈
• 英文名称: 6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylacetonitrile
• 英文别名: 3-cyanomethyl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine；3-Cyanmethyl-4.5-pentamethylen-1.2.4-triazol；(6,7,8,9-Tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-acetonitrile；2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)acetonitrile
• CAS: 116598-69-7
• 化学式: C₉H₁₂N₄
• mdl: MFCD00980781
• 分子量: 176.221
• InChiKey: PSFLXSYUOJMEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  54.5
• 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: (6,7,8,9-Tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepin-3-yl)-acetonitrile
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: (6,7,8,9-Tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepin-3-yl)-acetonitrile
CAS number: 116598-69-7

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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: C9H12N4
Molecular weight: 176.2

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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：

  (6,7,8,9-四氢-5H-[1,2,4]噻唑并[4,3-a]氮杂革-3-基)-乙腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-hydroxy-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)-2-butenenitrile
  参考文献：
  名称：

  Acylation of 6,7,8,9-tetrahydro-5H-[1,2,4]triazolo-[4,3-a]azepin-3-ylacetonitrile

  摘要：

  6,7,8,9-四氢-5H-[1,2,4]三唑并[4,3-a]氮杂卓-3-基乙腈会与羧酸酸酐和氯化物发生反应，根据条件和酰化剂的性质，在杂化碳原子或亚甲基碳原子上产生酰化产物。加热 N-酰基衍生物会导致酰基迁移，形成 C-酰基衍生物。

  DOI：

  10.1007/s11178-005-0104-3
• 作为产物：
  描述：

  1-氮杂-2-甲氧基-1-环庚烯 、 氰乙酰肼 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以89%的产率得到(6,7,8,9-四氢-5H-[1,2,4]噻唑并[4,3-a]氮杂革-3-基)-乙腈
  参考文献：
  名称：

  Study of reactions of lactim ethers with cyanoacetohydrazide

  摘要：

  乳酰醚与氰基乙酸肼反应的主要途径取决于起始乳酰醚的环尺寸。五元环的O-甲基丁酸内酯主要生成3-amino-4-(吡咯烷-2-亚胺)-4,5-二氢吡唑-5-酮，而六元和七元环的乳酰醚（分别为O-甲基戊酸内酯和O-甲基己酸内酯）的缩合反应则主要生成相应的多亚甲基三唑。

  DOI：

  10.1007/s11172-006-0466-x

文献信息

• Hydroxypropyl substituted nitrogen bridgehead fused cyanopyridines
  作者：Demyd S. Milokhov、Olga V. Khilya、Alexander V. Turov、Volodymyr V. Medviediev、Oleg V. Shishkin、Yulian M. Volovenko

  DOI：10.1016/j.tet.2013.12.074

  日期：2014.2

  promoted Michael addition of the substituted acetonitriles to 2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles followed by ring transformations has provided novel convenient synthetic methods to nitrogen bridgehead fused cyanopyridines bearing hydroxypropyl side chain. The structures of obtained compounds have been established based on NMR spectroscopy investigation and X-ray diffraction data.

  研究了2-杂芳基-2-（四氢-2-呋喃二烯）乙腈与取代乙腈作为C-亲核试剂的反应，并提出了反应机理。碱促进的取代基乙氧基到2-杂芳基-2-（四氢-2-呋喃腈）乙腈的迈克尔加成反应，然后进行环转化，为带有羟基丙基侧链的氮桥头稠合氰基吡啶提供了新颖便捷的合成方法。基于NMR光谱学研究和X射线衍射数据，已经建立了获得的化合物的结构。
• A One-Pot Fusion of Nitrogen-Containing Heterocycles
  作者：Dmitriy Volochnyuk、Sergey Ryabukhin、Andrey Plaskon、Alexander Shivanyuk、Andrey Tolmachev

  DOI：10.1055/s-2007-983842

  日期：2007.9

  Aromatic and heteroaromatic dialkylaminoaldehydes react with various active methylene compounds in the presence of Me3SiCl to give functionally and structurally diverse pyrrolo[1,2-a]quinolines, pyrido[1,2-a]quinolines, pyrazolo[3,4-e]indolizines, pyrazolo[4,3-c]quinolizines, benzo[g]pyrrolo[1,2-a]-1,8-naphthyridines, and benzo[g]pyrido[1,2-a]-1,8-naphthyridines in high yield and excellent purity.

  芳香族和杂芳香族二烷基氨基醛在 Me3SiCl 的存在下与各种活性亚甲基化合物反应，生成功能和结构多样的吡咯并[1,2-a]喹啉、吡啶并[1、2-a]喹啉类、吡唑并[3,4-e]吲嗪类、吡唑并[4,3-c]喹嗪类、苯并[g]吡咯并[1,2-a]-1,8-萘啶类和苯并[g]吡啶并[1,2-a]-1,8-萘啶类化合物的高产率和高纯度反应。
• Synthesis and evaluation of new 2,6-diamino-5-hetarylpyrimidines as inhibitors of dihydrofolate reductase
  作者：Olga V. Khilya、Demyd S. Milokhov、Lyudmyla A. Kononets、Oleksandr L. Kobzar、Andriy I. Vovk、Yulian M. Volovenko

  DOI：10.1007/s00706-017-2032-7

  日期：2018.4

  2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles with amidines have been developed. Some of 2,6-diamino-5-(1,3-benzothiazol-2-yl)pyrimidines were found to exhibit modest inhibitory activity against human dihydrofolate reductase. Molecular docking was performed to evaluate the binding mode of compounds of this series in the enzyme’s active site. Graphical abstract

  摘要已经开发了通过2-杂芳基-2-（四氢-2-呋喃基）乙腈与am的环转化反应制备6-氨基-5-杂芳基嘧啶衍生物的合成方法。发现一些2,6-二氨基-5-（1,3-苯并噻唑-2-基）嘧啶对人二氢叶酸还原酶显示适度的抑制活性。进行分子对接以评估该系列化合物在酶的活性位点的结合模式。 图形概要
• Petersen; Tietze, Chemische Berichte, 1957, vol. 90, p. 909,818
  作者：Petersen、Tietze

  DOI：——

  日期：——
• Study of reactions of lactim ethers with cyanoacetohydrazide
  作者：D. B. Nilov、V. G. Granik

  DOI：10.1007/s11172-006-0466-x

  日期：2006.9

  Main pathways in reactions of lactim ethers with cyanoacetic acid hydrazide depend on the ring size of the starting lactim ether. Five-membered O-methylbutyrolactim produces pre-dominantly 3-amino-4-(pyrrolidin-2-ylidene)-4,5-dihydropyrazol-5-one, whereas condensation of six-and seven-membered lactim ethers (O-methylvalero-and O-methylcaprolactim, respectively) affords the corresponding polymethylenetriazoles as the major products.

  乳酰醚与氰基乙酸肼反应的主要途径取决于起始乳酰醚的环尺寸。五元环的O-甲基丁酸内酯主要生成3-amino-4-(吡咯烷-2-亚胺)-4,5-二氢吡唑-5-酮，而六元和七元环的乳酰醚（分别为O-甲基戊酸内酯和O-甲基己酸内酯）的缩合反应则主要生成相应的多亚甲基三唑。