2-氨基-4,5-二甲基噻吩-3-羧酰胺 | 51486-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-4,5-二甲基噻吩-3-羧酰胺
• 中文别名: 2-氨基-4,5-二甲基噻吩-3-甲酰胺
• 英文名称: 2-amino-4,5-dimethylthiophene-3-carboxamide
• CAS: 51486-04-5
• 化学式: C₇H₁₀N₂OS
• mdl: MFCD00617251
• 分子量: 170.235
• InChiKey: ZKXSEMXZKAQARN-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C(Solv: water (7732-18-5))
• 沸点：
  252.1±40.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8°C，避光，惰性气体保护。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4,5-dimethylthiophene-3-carboxamide
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-4,5-dimethylthiophene-3-carboxamide
CAS number: 51486-04-5

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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: C7H10N2OS
Molecular weight: 170.2

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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, sulfur 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-氨基-4,5-二甲基噻吩-3-羧酰胺 在 氯化亚砜 作用下， 以66%的产率得到5,6-Dimethyl-2-oxo-2,3-dihydro-1H-2λ⁴-thieno[2,3-c][1,2,6]thiadiazin-4-one
  参考文献：
  名称：

  双环1,2,6-噻二嗪的合成

  摘要：

  来自吡咯、呋喃和噻吩系列的α-氨基酸酰胺转化为新的硫杂环。正在研究这些化合物的稳定性。

  DOI：

  10.1002/ardp.19813140213
• 作为产物：
  描述：

  2-氨基-3-腈基-4,5-二甲基噻吩 在 硫酸 、 水 作用下， 反应 2.0h， 以80%的产率得到2-氨基-4,5-二甲基噻吩-3-羧酰胺
  参考文献：
  名称：

  噻吩并[2,3- d ]嘧啶衍生物的碘催化合成及抗菌评价

  摘要：

  已经开发了通过碘催化 2-氨基-4,5-二甲基噻吩-3-甲酰胺与芳香醛的杂环化，一步得到一系列噻吩并 [2,3-d] 嘧啶衍生物的新路线。这些化合物中的一些表现出与作为参考药物的链霉素相当的抗菌活性。

  DOI：

  10.3184/030823409x12537299044500

文献信息

• Exploiting Drug-Resistant Enzymes as Tools To Identify Thienopyrimidinone Inhibitors of Human Immunodeficiency Virus Reverse Transcriptase-Associated Ribonuclease H
  作者：Takashi Masaoka、Suhman Chung、Pierluigi Caboni、Jason W. Rausch、Jennifer A. Wilson、Humeyra Taskent-Sezgin、John A. Beutler、Graziella Tocco、Stuart F. J. Le Grice

  DOI：10.1021/jm400405z

  日期：2013.7.11

  The thienopyrimidinone 5,6-dimethyl-2-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (DNTP) occupies the interface between the p66 ribonuclease H (RNase H) domain and p51 thumb of human immunodeficiency virus reverse transcriptase (HIV RT), thereby inducing a conformational change incompatible with catalysis. Here, we combined biochemical characterization of 39 DNTP derivatives with antiviral testing

  噻吩并嘧啶酮5,6-二甲基-2-(4-硝基苯基)噻吩并[2,3 - d ]嘧啶-4(3 H)-one (DNTP) 占据 p66 核糖核酸酶 H (RNase H) 域和人类免疫缺陷病毒逆转录酶 (HIV RT) 的 p51 拇指之间的界面，从而导致与催化不相容的构象变化。在这里，我们将 39 种 DNTP 衍生物的生化表征与所选化合物的抗病毒测试相结合。除了野生型 HIV-1 RT，还使用合理设计的 p66/p51 异二聚体对衍生物进行了评估，这些异二聚体表现出高水平的 DNTP 敏感性或抗性。该策略鉴定了 3',4'-二羟基苯基（儿茶酚）取代的噻吩并嘧啶酮，对野生型 HIV-1 RT 和耐药变体具有亚微摩尔的体外活性。热位移分析表明，与活性位点 RNase H 抑制剂相比，这些噻吩并嘧啶酮会破坏稳定酶，在某些情况下将T m降低 5 °C。重要的是，含有儿茶酚的噻吩并嘧啶酮还抑制细胞中的
• Synthesis of Some New 2-Arylthieno[2,3-d]Pyrimidin-4(3H)-One Derivatives
  作者：Abolghasem Davoodnia、Hossein Eshghi、Akram Salavaty、Niloofar Tavakoli-Hoseini

  DOI：10.3184/030823408x283685

  日期：2008.1

  Some new derivatives of 2-arylthieno[2,3-d]pyrimidin-4(3H)-ones have been prepared through a condensation reaction of 2-amino-4,5-dimethylthiophene-3-carboxamide with aroyl halides in boiling pyridine followed by cyclisation with 10% NaOH.

  通过2-氨基-4,5-二甲基噻吩-3-甲酰胺与芳酰卤在沸腾吡啶中的缩合反应，制备了2-芳基噻吩并[2,3-d]嘧啶-4(3H)-酮的一些新衍生物。用 10% NaOH 环化。
• New route to 2-arylthieno[2,3-d]pyrimidin-4(3H)-ones and isolation of the unoxidized intermediates
  作者：Abolghasem Davoodnia、Mehdi Bakavoli、Mehdi Soleimany、Niloofar Tavakoli-Hoseini

  DOI：10.1007/s00706-008-0032-3

  日期：2009.3

  AbstractA new route to the synthesis of 2-arylthieno[2,3-d]pyrimidin-4(3H)-ones has been developed through heterocyclization of 2-amino-4,5-dimethylthiophene-3-carboxamide with aromatic aldehydes in boiling glacial acetic acid followed by air oxidation. The unoxidized intermediates, 2-aryl-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones, are isolated when the reactions are carried out either at room temperature

  摘要通过在沸腾的冰河中将2-氨基-4,5-二甲基噻吩-3-羧酰胺与芳香醛杂环化，已开发出一种合成2-芳基噻吩并[2,3-d]嘧啶-4（3H）-的新途径。醋酸，然后进行空气氧化。当在室温或在氮气氛下进行反应时，分离出未氧化的中间体2-芳基-2,3-二氢噻吩并[2,3- d ]嘧啶-4（1 H）-酮。 图形概要
• Investigation into the reaction of 2-amino-4,5-dimethylthiophene-3-carboxamide with iso(and isothio)cyanates under microwave irradiation
  作者：Abolghasem Davoodnia、Mohammad Rahimizadeh、Hoda Atapour-Mashhad、Niloofar Tavakoli-Hoseini

  DOI：10.1002/hc.20557

  日期：——

  with iso(and isothio) cyanates for the synthesis of thieno[2,3-d]pyrimidines has been investigated. The reactions under microwave irradiation in the presence of N,N-dimethyl acetamide as solvent gave 5,6-dimethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione, 5,6-dimethyl-2-thioxo-2,3-dihy- drothieno[2,3-d]pyrimidin-4(1H)-one, and 2-aryla- mino-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one derivatives. These

  已经研究了 2-氨基-4,5-二甲基-噻吩-3-甲酰胺与异（和异硫代）氰酸酯的反应，用于合成噻吩并 [2,3-d] 嘧啶。以N,N-二甲基乙酰胺为溶剂，在微波照射下反应得到5,6-二甲基噻吩并[2,3-d]嘧啶-2,4(1H,3H)-二酮，5,6-二甲基-2 -thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one, and 2-aryla-mino-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H) )-一种衍生物。这些反应可能通过中间体 4,5-二甲基-2-取代氨基甲硫基氨基噻吩-3-甲酰胺进行。分离出这些中间体中的两种。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:346–349, 2009; 在线发表于 Wiley InterScience (www.interscience
• Heterocyclic Derivatives
  申请人：Gillen Kevin James

  公开号：US20080255086A1

  公开（公告）日：2008-10-16

  The present invention relates to a heterocyclic derivative according to formula I wherein the variables are defined as in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to a pharmaceutical composition comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer's disease.

  本发明涉及式I的杂环衍生物，其中变量如规范中所定义，或其药学上可接受的盐或溶剂。本发明还涉及包含上述杂环衍生物的制药组合物，以及它们在治疗中的使用，例如在需要增强由AMPA受体介导的突触反应的精神疾病的治疗或预防中，包括精神分裂症、抑郁症和阿尔茨海默病。