2-氨基-4,7-二氢-5H-噻吩并[2,3-c]吡喃-3-羧酸乙酯 | 117642-16-7

• 物质功能分类: 医药中间体 - 杂环化合物
• 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-羧酸乙酯
• 中文别名: 2-氨基-4,7-二氢噻吩[2,3-C]吡喃-3-羧酸乙酯
• 英文名称: 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid ethyl ester
• 英文别名: 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylic acid ethyl ester；ethyl 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylate；ethyl 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate
• CAS: 117642-16-7
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: RRKGPBYCHQFJEG-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  431.8±45.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 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：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-amino-4H,5H,7H-thieno[2,3-c]pyran-3-carboxylate
Synonyms: Ethyl 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-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 2-amino-4H,5H,7H-thieno[2,3-c]pyran-3-carboxylate
CAS number: 117642-16-7

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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, under −20◦C.
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: C10H13NO3S
Molecular weight: 227.3

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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, 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

制备方法与用途

应用

2-氨基-4,7-二氢噻吩[2,3-C]吡喃-3-羧酸乙酯是一种医药中间体，在实验室研发和化工生产中均有广泛应用。

制备

将四氢-4H-吡喃-4-酮（2.00g，20.0mmol）、氰乙酸乙酯（2.50g，22.0mmol）和硫（704mg，22.0mmol）溶解在30.0mL乙醇中。随后加入吗啉（1.74g，20.0mmol），并在50℃条件下搅拌过夜。通过TLC检测反应进度，在完成反应后，使用乙酸乙酯和水对反应液进行萃取，并分离上层有机相并蒸干。经过柱层析纯化后得到淡黄色固体，即为2-氨基-4,7-二氢噻吩[2,3-C]吡喃-3-羧酸乙酯（产率96%）。

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-羧酸乙酯 以 乙酸乙酯 为溶剂， 以the title compound (907 mg, yield 52%) was obtained by an operation similar to that of Reference Example 45 and trituration with ethyl acetate的产率得到2-Amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid
  参考文献：
  名称：

  SPIRO-CYCLIC COMPOUND

  摘要：

  本发明提供了一种由公式(I)表示的化合物：其中E是可选取代的环状基团；D是羰基基团或磺酰基团；A是CH或N；环P是可选取代的5-至7-成员环；环Q是可选取代的5-至7-成员非芳香环；环R是可选取代和可选缩合的5-至7-成员非芳香环，或其盐。本发明的化合物具有ACC抑制活性，对于预防或治疗肥胖症、糖尿病、高血压、高脂血症、心力衰竭、糖尿病并发症、代谢综合征、肌肉萎缩等疾病有用，并具有优越的疗效、活性持续时间、特异性、低毒性等特点。

  公开号：

  US20100160255A1
• 作为产物：
  描述：

  ethyl 2-cyano-2-(dihydro-2H-pyran-4(3H)-ylidene)acetate 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-羧酸乙酯
  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

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• [EN] ANTI-HIV COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VIH
  申请人：PANACOS PHARMACEUTICALS INC

  公开号：WO2009085256A1

  公开（公告）日：2009-07-09

  Thiazole derivatives represented by Formula (I) are disclosed, where R1, R2, R3, A, X, Y, Z, R6 and R7 are disclosed herein. These thiazole derivatives and pharmaceutical compositions comprising these derivatives are useful in the treatment of HIV mediated diseases and conditions.

  公式（I）代表的噻唑衍生物已被披露，其中在此披露了R1、R2、R3、A、X、Y、Z、R6和R7。这些噻唑衍生物和包含这些衍生物的药物组合物在治疗HIV介导的疾病和症状方面是有用的。
• 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
• [EN] ANTHELMINTIC AND INSECTICIDAL THIOPHENE DERIVATIVES<br/>[FR] VERMIFUGES ET INSECTICIDES A BASE DE DERIVES THIOPHENIQUES
  申请人：UPJOHN CO

  公开号：WO2003101979A1

  公开（公告）日：2003-12-11

  Novel anthelmintic compositions containing thiophene derivatives as active ingredients are disclosed.

  新的含有噻吩衍生物作为活性成分的驱虫剂组合物被揭示。
• 4-amino-5,6-substituted thiopheno [2,3-d] pyrimidines, pharmaceutical compositions containing the same, and their use in the treatment or prevention of PDE7B-mediated diseases and conditions
  申请人：——

  公开号：US20030119829A1

  公开（公告）日：2003-06-26

  The invention relates to 4-amino-5,6-substituted thiopheno [2,3-d] pyrimidines, pharmaceutical compositions containing the same and their use to treat or prevent diseases and conditions mediated by the phosphodiesterase enzyme 7 B (PDE7 B ). Diseases and conditions mediated by PDE7 B include osteoporosis, osteopenia and asthma.

  该发明涉及4-氨基-5,6-取代噻吩[2,3-d]嘧啶，包含这些化合物的药物组合物以及它们用于治疗或预防由磷酸二酯酶7B（PDE7B）介导的疾病和症状的用途。由PDE7B介导的疾病和症状包括骨质疏松症、骨质疏松症和哮喘。