2-氨基-4,7-二氢-5H-噻吩并[2,3-c]吡喃-3-甲腈 | 150986-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡喃类
• 中文名称: 2-氨基-4,7-二氢-5H-噻吩并[2,3-c]吡喃-3-甲腈
• 英文名称: 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carbonitrile
• 英文别名: 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carbonitrile
• CAS: 150986-82-6
• 化学式: C₈H₈N₂OS
• 分子量: 180.23
• InChiKey: XCCSOSJCWRZLPA-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227°C
• 沸点：
  434.7±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4H,5H,7H-thieno[2,3-c]pyran-3-carbonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-4H,5H,7H-thieno[2,3-c]pyran-3-carbonitrile
CAS number: 150986-82-6

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8N2OS
Molecular weight: 180.2

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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-4,7-二氢-5H-噻吩并[2,3-c]吡喃-3-甲腈 在 溶剂黄146 作用下， 生成 1-(3-chloro-4-(methyl)phenyl)-3-(4-[(5,8 dihydro-6H-pyrano[4',3':4,5] thieno[2,3d] pyrimidin-4-yl)amino]phenyl)urea
  参考文献：
  名称：

  以噻吩并嘧啶骨架为靶标的某些VEGFR-2抑制剂的设计，合成和分子模型研究

  摘要：

  设计，合成和评价了不同系列的新型噻吩并[2，3- d ]嘧啶衍生物（9a-d，10a-f，l，m和15a-m）在体外抑制VEGFR-2酶的能力。而且，通过NCI对60种不同的人类癌细胞系进行了测试，以测试最终化合物的细胞毒性。VEGFR-2酶的抑制结果表明，化合物10d，15d和15 g是活性最高的抑制剂，IC 50值分别为2.5、5.48和2.27 µM，而化合物10a显着显示出最高的细胞生长抑制率，平均生长抑制率（GI）为31.57％。它对几种NCI细胞系表现出广谱的抗增殖活性，特别是对人乳腺癌（T7-47D）和肾癌（A498）细胞系分别具有85.5％和77.65％的抑制作用。为了研究该活性的机制，对化合物10a进行了进一步的生物学研究，例如流式细胞术细胞周期与caspase-3比色测定。对MCV-7和PC-3癌细胞的流式细胞仪分析表明，它诱导了G0-G1期的细胞周期停滞，并通过激活c

  DOI：

  10.1016/j.bioorg.2018.10.008
• 作为产物：
  描述：

  4-哌喃亚甲基丙二腈 在 三乙烯二胺 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 水 为溶剂， 反应 5.0h， 生成 2-氨基-4,7-二氢-5H-噻吩并[2,3-c]吡喃-3-甲腈
  参考文献：
  名称：

  DABCO水溶液，一种用于快速有机催化Knoevenagel缩合和Gewald反应的有效介质

  摘要：

  在水和1,4-二氮杂双环[2.2.2]辛烷的存在下，几种醛和环状酮与丙二腈和氰基乙酸乙酯进行有效的Knoevenagel缩合反应，从而在相当短的时间内产生各自的ab-不饱和体系。结果，容易获得高收率的结合产物。产物可以逐步地或原位地进行Gewald反应，以在4--7小时内有效地产生它们各自的2-氨基噻吩。

  DOI：

  10.3906/kim-1309-38

文献信息

• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation
  作者：Hong-Xu Xie、Juan Zhang、Yue Li、Jin-He Zhang、Shan-Kui Liu、Jie Zhang、Hua Zheng、Gui-Zhou Hao、Kong-Kai Zhu、Cheng-Shi Jiang

  DOI：10.1016/j.bioorg.2021.105236

  日期：2021.10

  α-Glucosidase inhibitors, which can inhibit the digestion of carbohydrates into glucose, are one of important groups of anti-type 2 diabetic drugs. In the present study, we report our effort on the discovery and optimization of α-glucosidase inhibitors with tetrahydrobenzo[b]thiophen-2-yl)urea core. Screening of an in-house library revealed a moderated α-glucosidase inhibitors, 5a, and then the following

  α-葡萄糖苷酶抑制剂是一类重要的抗2型糖尿病药物，可抑制碳水化合物消化为葡萄糖。在本研究中，我们报告了我们在发现和优化具有四氢苯并[ b ]噻吩-2-基)脲核心的α-葡萄糖苷酶抑制剂方面的努力。内部文库的筛选揭示了一种缓和的 α-葡萄糖苷酶抑制剂，5a，然后进行以下结构优化以获得更有效的衍生物。与亲本化合物5a (IC 50为 26.71 ± 1.80 μM) 和阳性对照阿卡波糖 (IC 50为 258.53 ± 1.27 μM)相比，大多数这些衍生物对 α-葡萄糖苷酶的抑制活性增加。其中，化合物8r (IC 50  = 0.59 ± 0.02 μM) 和8s (IC 50  = 0.65 ± 0.03 μM) 是最有效的抑制剂，并且表现出优于 α-淀粉酶的选择性。荧光猝灭实验证实了两种化合物与α-葡萄糖苷酶的直接结合。动力学研究表明，这些化合物是非竞争性抑制剂，这与分子对接结果一致，即化
• Novel substituted 3-cyanothiophene acetamides as glucagon receptor antagonists
  申请人：——

  公开号：US20040209943A1

  公开（公告）日：2004-10-21

  The present invention relates to compounds of formula (I) 1 wherein R1, R2, R3, R4 and n are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the antagonism of the glucagon receptor, such as diabetes.

  本发明涉及式(I)1的化合物，其中R1、R2、R3、R4和n如描述和索赔中所定义，并且其药学上可接受的盐。这些化合物对于治疗和/或预防与胰高血糖素受体拮抗有关的疾病，如糖尿病，是有用的。
• 2-(Benzoylimino)thiazolidin-4-ones: Formation by an Alternative Ring Closure and Analysis of Rotational Barriers
  作者：Michael Gütschow、Hans-Georg Häcker、Paul Elsinghorst、Susanne Michels、Jörg Daniels、Gregor Schnakenburg

  DOI：10.1055/s-0028-1087995

  日期：2009.4

  The reactions of N-benzoyl-N′-(o-cyanoaryl)thioureas with ethyl bromoacetate under alkaline conditions led to the form­ation of either fused 2-(alkylsulfanyl)-4-aminopyrimidines or 2-(benzoylimino)-3-(o-cyanoaryl)thiazolidin-4-ones. The accurate application of slightly different reaction conditions allowed us to adjust the balance between the formation of the pyrimidine or thiazolidine heterocycles. Atropisomerism in the 3-(o-cyanoaryl)thiazolidin-4-ones was influenced by the size of the o-cyanoaryl ring, which was investigated by means of NMR measurements and theoretical calculations.

  在碱性条件下，N-苯甲酰基-N′-（邻氰基芳基）硫脲与溴乙酸乙酯反应，生成融合的 2-（烷基硫酰基）-4-氨基嘧啶或 2-（苯甲酰基亚氨基）-3-（邻氰基芳基）噻唑烷-4-酮。通过准确地应用略有不同的反应条件，我们可以调整嘧啶或噻唑烷杂环形成之间的平衡。3-(o-氰基芳基)噻唑烷-4-酮中的异构体受邻氰基芳基环大小的影响，这一点通过核磁共振测量和理论计算进行了研究。
• Synthesis of New Fused Pyrimidines by Isocyanate and Isothiocyanate.
  作者：A.Z.M. Shaifullah CHOWDHURY、Yasuyuki SHIBATA

  DOI：10.1248/cpb.49.391

  日期：——

  o-Aminonitrile or o-aminoester compounds were cyclized to fused pyrimidines by reacting with ethyl iso(thio)cyanatoacetate in pyridine, and then were methylated, halogenated and subsequently displaced by the amines studied.

  通过与异（硫）氰基乙酸乙酯在吡啶中反应，将邻氨基腈或邻氨基酯化合物环化成稠合的嘧啶，然后将其甲基化，卤化，然后用所研究的胺置换。