噻吩-3-甲酸乙酯 | 5751-80-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 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: 噻吩-3-甲酸乙酯
• 中文别名: 乙基噻吩-3-甲酸酯；噻吩-3-羧酸乙酯；3-噻吩甲酸乙酯
• 英文名称: thiophene-3-carboxylic acid ethyl ester
• 英文别名: ethyl thiophene-3-carboxylate；ethyl 3-thiophenecarboxylate
• CAS: 5751-80-4
• 化学式: C₇H₈O₂S
• 分子量: 156.205
• InChiKey: OYSLMAQEMAJMCL-UHFFFAOYSA-N

物化性质

• 沸点：
  97-98 °C (8 mmHg)
• 密度：
  1.12
• 闪点：
  103 °C
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  建议在0-6℃下避光、存放在阴凉干燥处并密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl thiophene-3-carboxylate
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: Ethyl thiophene-3-carboxylate
CAS number: 5751-80-4

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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: C7H8O2S
Molecular weight: 156.2

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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, 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：

  噻吩-3-甲酸乙酯 在 ammonium hydroxide 、 sodium ethanolate 、 四氯化锡 作用下， 反应 28.0h， 生成 thiophenfurin
  参考文献：
  名称：

  呋喃呋喃和噻吩呋喃：两种新型的噻唑啉类似物。合成，结构，抗肿瘤活性以及与肌苷单磷酸脱氢酶的相互作用。

  摘要：

  描述了噻唑呋喃的呋喃和噻吩类似物（分别为呋喃呋喃和噻吩呋喃）的合成。用1,2,3,5-四-O-乙酰基-D-呋喃呋喃糖将三呋喃甲酸乙酯（6）或3-噻吩甲酸乙酯（18）直接用氯化锡催化的C-糖基化反应得到2-和5-糖基化的区域异构体，是α和β异头异构体的混合物，以及β-2,5-二糖基化衍生物。5-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）呋喃-3-羧酸酯（9 beta）和5-（2,3,5-三-O-乙酰基-乙基-乙基的脱保护β-D-呋喃呋喃糖基）噻吩-3-羧酸盐（20 beta）与乙醇钠制得5-β-D-呋喃呋喃糖基呋喃-3-羧酸乙酯（12 beta）和5-β-D-呋喃呋喃糖基噻吩-3-羧酸乙酯（23 β）转化为5-β-D-呋喃呋喃糖基呋喃-3-羧酰胺（呋喃呋喃，4）和5-β-D-呋喃呋喃糖基噻吩-3-甲酰胺（thiophenfurin，5）与氢氧化铵反应。通过1 H-NMR和质子-质子

  DOI：

  10.1021/jm00019a013
• 作为产物：
  描述：

  3-噻吩甲酸 在 硫酸 作用下， 以 乙醇 为溶剂， 以88%的产率得到噻吩-3-甲酸乙酯
  参考文献：
  名称：

  苯并噻唑类化合物及医药用途

  摘要：

  本发明公开了一种苯并噻唑类化合物及其医药用途，具体涉及如式I所示的苯并噻唑类化合物及其医药用途，尤其涉及苯并噻唑类化合物作为USP7C端结构域调控剂在预防和治疗骨髓增生异常综合征及恶性肿瘤的药物中的用途。本发明式I所示苯并噻唑类化合物或其药学上可接受的盐或溶剂化物与USP7C端蛋白具有很强的结合力，并可以降低肿瘤细胞中DNMT1的蛋白水平，因而可应用在制备USP7调控剂，同时具有显著的抗肿瘤细胞增殖作用，可以用于制备预防或治疗骨髓增生异常综合征及恶性肿瘤的药物。

  公开号：

  CN111763201A

文献信息

• Rhodium-Catalyzed Selective Olefination of Arene Esters via C−H Bond Activation
  作者：Sae Hume Park、Ji Young Kim、Sukbok Chang

  DOI：10.1021/ol200600p

  日期：2011.5.6

  A new catalytic procedure of ortho-olefination of benzoates and benzaldehydes has been developed. Ester and carboxaldehyde units were revealed to be effective chelating groups in focusing the activation of aryl C−H bonds ortho to the directing moieties under the Rh-catalyzed oxidative conditions. The reaction is highly regioselective with a range of benzoates and benzaldehydes enabling the efficient

  已经开发出一种新的苯甲酸酯和苯甲醛正烯烃聚合的催化方法。揭示酯和羧醛单元是有效的螯合基团，其在Rh催化的氧化条件下将芳基CH键的邻位活化集中到引导部分上。该反应对多种苯甲酸酯和苯甲醛具有高度区域选择性，从而可以与丙烯酸酯，丙烯酸和苯乙烯进行有效的烯化反应。
• [EN] COMPOUNDS AND METHODS FOR MODULATING FXR<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR MODULER LE FXR
  申请人：LILLY CO ELI

  公开号：WO2009012125A1

  公开（公告）日：2009-01-22

  Compounds of formula (I): formula (I) wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and diseases related to dyslipidemia.

  公式(I)的化合物：其中变量如本文所述定义，其药物组合物及其用途被披露为用于治疗血脂异常以及与血脂异常相关的疾病。
• Manganese Catalyzed Direct Amidation of Esters with Amines
  作者：Zhengqiang Fu、Xinghua Wang、Sheng Tao、Qingqing Bu、Donghui Wei、Ning Liu

  DOI：10.1021/acs.joc.0c02478

  日期：2021.2.5

  metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines

  酯与胺的过渡金属催化的酰胺键形成反应已被开发为克服传统方法的缺点的先进方法。在过渡金属催化的酰胺化反应中底物的广泛应用仍然是一个挑战。在此，报道了锰（I）催化的方法，其由多种酯和胺直接合成酰胺，具有低催化剂载量，具有无与伦比的底物范围。甚至在脂肪酸酯中，各种各样的芳族，脂族和杂环酯也与各种各样的伯芳基胺，伯烷基胺和仲烷基胺反应形成酰胺。值得注意的是，该方法提供了由脂肪酸酯和胺形成过渡金属催化的酰胺键形成反应的第一个例子。
• 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Alice Legru、Federica Verdirosa、Laurent Sevaille、Lionel Nauton、Giuseppina Corsica、Paola Sandra Mercuri、Filomena Sannio、Georges Feller、Rémi Coulon、Filomena De Luca、Giulia Cerboni、Silvia Tanfoni、Giulia Chelini、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.bioorg.2021.105024

  日期：2021.8

  (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如
• An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters
  作者：Cheng Qian、Jiayan Chen、Meiqin Fu、Shiya Zhu、Wen-Hua Chen、Huanfeng Jiang、Wei Zeng

  DOI：10.1039/c3ob41011k

  日期：——

  The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation.

  钯催化的芳基硼酸与N-芳基α-亚胺酯的交叉偶联乙氧羰基化反应，通过碳基-亚胺σ键断裂形成芳基羧酸酯。这种前所未有的反应模式允许将乙氧羰基团区域选择性地安装到目标分子中。机理研究表明，在该转化过程中涉及了一种不寻常的1,2-芳基迁移过程。