ethyl (2E)-3-(3-thienyl)propenoate | 50266-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2E)-3-(3-thienyl)propenoate
• 英文别名: ethyl 3-(3-thienyl)propenoate；3-thiophen-3-yl-acrylic acid ethyl ester；ethyl 3-(thiophen-3-yl)acrylate；ethyl 3-thiophen-3-ylprop-2-enoate
• CAS: 50266-60-9
• 化学式: C₉H₁₀O₂S
• 分子量: 182.243
• InChiKey: JVKOMXUTXGBJFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (E)-Ethyl 3-(thiophen-3-yl)acrylate
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: (E)-Ethyl 3-(thiophen-3-yl)acrylate
CAS number: 50266-60-9

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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: C9H10O2S
Molecular weight: 182.2

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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：

  ethyl (2E)-3-(3-thienyl)propenoate 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 生成 (E)-3-(thiophen-3-yl)prop-2-en-1-ol
  参考文献：
  名称：

  铜催化氢胺化不对称合成 γ-氨基醇。

  摘要：

  开发了通过铜催化加氢胺化策略从未保护的烯丙醇不对称合成γ-氨基醇的方法。使用易于获得的起始原料，制备了一系列具有优异区域选择性和对映选择性的手性 1,3-氨基醇。此外，该方案为以分子间方式对映选择性合成 γ-氨基醇提供了一种有效的一步方法。

  DOI：

  10.1021/acs.orglett.9b03356
• 作为产物：
  描述：

  3-噻吩甲醛 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以82.7%的产率得到ethyl (2E)-3-(3-thienyl)propenoate
  参考文献：
  名称：

  [EN] TRICYCLIC HETEROARYL PIPERAZINES, PYRROLIDINES AND AZETIDINES AS SEROTONIN RECEPTOR MODULATORS
  [FR] HETEROARYLE PIPERAZINES TRICYCLIQUES, PYRROLIDINES ET AZETIDINES UTILES EN TANT QUE MODULATEURS DU RECEPTEUR DE LA SEROTONINE

  摘要：

  公开号：

  WO2006028961A3

文献信息

• Cobalt‐Catalyzed Radical Hydroamination of Alkenes with <i>N</i> ‐Fluorobenzenesulfonimides
  作者：Tao Qin、Guowei Lv、Qi Meng、Ge Zhang、Tao Xiong、Qian Zhang

  DOI：10.1002/anie.202110178

  日期：2021.12

  N-fluorobenzenesulfonimide (NFSI) and its analogues as both nitrogen source and oxidant was successfully disclosed. A variety of alkenes, including aliphatic alkenes, styrenes, α, β-unsaturated esters, amides, acids, as well as enones, were all compatible to provide desired amination products. Mechanistic experiments suggest that the reaction underwent a metal-hydride-mediated hydrogen atom transfer (HAT) with alkene

  成功地公开了使用 Co(salen) 作为催化剂、N-氟苯磺酰亚胺 (NFSI) 及其类似物作为氮源和氧化剂的烯烃的有效和通用自由基加氢胺化。各种烯烃，包括脂肪族烯烃、苯乙烯、α, β-不饱和酯、酰胺、酸以及烯酮，都可以提供所需的胺化产物。机理实验表明，该反应与烯烃进行了金属氢化物介导的氢原子转移 (HAT)，然后是关键的催化剂控制原位生成的有机钴 (IV) 物质和氮基亲核试剂之间的类 SN 2 途径。此外，借助改性手性钴 (II)-salen 催化剂，还实现了前所未有的不对称版本，具有良好到出色的对映控制水平。
• An Efficient and Versatile Approach for the Immobilization of Carbene Precursorsvia Copper-Catalyzed [3+2]-Cycloaddition and their Catalytic Application
  作者：Kirsten Zeitler、Ina Mager

  DOI：10.1002/adsc.200700174

  日期：2007.8.6

  azide-functionalized support via copper-catalyzed 1,3-dipolar cycloaddition, which efficiently yields a rigid and robust 1,2,3-triazole linkage. The catalytic performance of the corresponding nucleophilic carbenes (NHCs) was examined in intramolecular Stetter reactions (chroman-4-one products) and organocatalytic redox esterifications (α,β-unsaturated esters). The MeOPEG-immobilized organocatalysts are

  可以通过铜催化的1,3-偶极环加成将不同种类的炔基取代的杂唑衍生物共价固定在叠氮化物官能化的支持物上，这有效地产生了刚性且牢固的1,2,3-三唑键。在分子内Stetter反应（苯并四氢呋喃产物）和有机催化氧化还原酯化反应（α，β-不饱和酯）中检查了相应亲核碳烯（NHC）的催化性能。固定有MeOPEG的有机催化剂具有很高的活性，并显示出与非负载衍生物相当的非对映选择性。此外，它们还简化了后处理程序，并且已被证明可回收利用。
• Synergistic Relay Reactions To Achieve Redox‐Neutral α‐Alkylations of Olefinic Alcohols with Ruthenium(II) Catalysis
  作者：Chen‐Chen Li、Jian Kan、Zihang Qiu、Jianbin Li、Leiyang Lv、Chao‐Jun Li

  DOI：10.1002/anie.201915218

  日期：2020.3.9

  the first Grignard-type nucleophilic addition using olefinic alcohols as latent carbonyl groups, providing a higher yield of the corresponding secondary alcohol than the classical hydrazone addition to aldehydes does. A broad scope of unsaturated alcohols and hydrazones, including some complex structures, can be successfully employed in this reaction, which shows the versatility of this approach and

  本文中，我们报告了基于不饱和醇的钌催化氧化还原中性α-烷基化，其基于涉及烯烃异构化（链走）和and酚的协同中继过程，该过程利用了两个效率很低的单独反应步骤之间的相互作用实现高效的整体流程。这种转化显示了-型“碳负离子”和活性质子在一锅反应中的相容性，并且同时使用烯烃醇作为潜在的羰基实现了首次格氏式亲核加成，从而提供了更高产率的相应仲醇比传统的除醛还要多。广泛的不饱和醇和，包括一些复杂的结构，可以成功地用于该反应，
• Practical Route to 2-Quinolinones via a Pd-Catalyzed C–H Bond Activation/C–C Bond Formation/Cyclization Cascade Reaction
  作者：Junliang Wu、Shaohua Xiang、Jing Zeng、Minli Leow、Xue-Wei Liu

  DOI：10.1021/ol503292p

  日期：2015.1.16

  Quinolinone derivatives were constructed via a Pd-catalyzed C–H bond activation/C–C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.

  喹啉酮衍生物是通过Pd催化的C–H键活化/ CC键形成/环化级联过程构建的，并以简单的苯胺为底物。该发现为合成含喹啉酮的生物碱和药物分子提供了实用的程序。蒂法法尼的正式合成证明了该方法的实用性。
• Organocatalytic Asymmetric Aldol Reaction of Hydroxyacetone with β,γ-Unsaturated α-Keto Esters: Facile Access to Chiral Tertiary Alcohols
  作者：Chen Liu、Xiaowei Dou、Yixin Lu

  DOI：10.1021/ol2021274

  日期：2011.10.7

  An efficient direct asymmetric aldol reaction between hydroxyacetone and β,γ-unsaturated α-keto esters has been successfully developed. In the presence of 9-amino-9-deoxy-epi-cinchonine and trifluoroacetic acid, the direct aldol reaction of O-protected hydroxyacetone proceeded in a highly enantioselective manner, affording the desired adducts containing a chiral tertiary alcohol in high yields and

  已经成功开发了羟基丙酮与β，γ-不饱和α-酮酯之间有效的直接不对称醛醇缩合反应。在9-氨基-9-脱氧-表-辛可宁和三氟乙酸的存在下，O-保护的羟基丙酮的直接醛醇缩合反应以高度对映选择性的方式进行，从而以高收率和优异的收率提供了所需的含手性叔醇的加合物。对映选择性。所得的醇醛产物是用于合成2-取代的甘油衍生物的有价值的前体。