ethyl (E)-4-phenylbut-3-enoate | 1205-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (E)-4-phenylbut-3-enoate
• 英文别名: ethyl (E)-4-phenyl-3-butenoate；(E)-ethyl 4-phenylbut-3-enoate；ethyl (3E)-4-phenyl-3-butenoate；Ethyl 4-phenylbut-3-enoate
• CAS: 1205-84-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QGHDRPQXRRBNNR-RMKNXTFCSA-N

物化性质

• 沸点：
  293.9±19.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl trans-4-phenyl-2-butenoate
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 trans-4-phenyl-2-butenoate
CAS number: 1205-84-1

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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: C12H14O2
Molecular weight: 190.2

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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.

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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 (E)-4-phenylbut-3-enoate 在 三溴化磷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 生成 [(1E)-4-溴-1-丁烯-1-基]苯
  参考文献：
  名称：

  Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections

  摘要：

  Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 mu M). Notably, compound 5m (1 mu M) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 mu g/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.

  DOI：

  10.1021/acs.jmedchem.5b01984
• 作为产物：
  描述：

  ethyl 2-diazo-4-phenylbutanoate 在 copper acetylacetonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 ethyl (E)-4-phenylbut-3-enoate
  参考文献：
  名称：

  重氮酯的连续流生成及其直接用于S–H和P–H插入反应：α-硫烷基，α-磺酰基和α-膦酰基羧酸酯的合成

  摘要：

  α-硫烷基，α-磺酰基和α-膦酰基羧酸酯的合成已通过两步程序完成，涉及从磺酰hydr通过Bamford-Stevens消除流程流入重氮酯的过程，然后再进行SH和亚磺酸盐的合成。和PH卡宾插入反应。α-磺酰基酯的方法特别值得注意，因为它代表了一种非常经济的原子（“绿色”）获取产品的方式，并且完全避免了使用卤代烷。

  DOI：

  10.1016/j.tet.2013.01.020

文献信息

• Oxidative addition of N-halosuccinimides to palladium(0): the discovery of neutral palladium(II) imidate complexes, which enhance Stille coupling of allylic and benzylic halides
  作者：Catherine M. Crawforth、Suzanne Burling、Ian J.S. Fairlamb、Anant R. Kapdi、Richard J.K. Taylor、Adrian C. Whitwood

  DOI：10.1016/j.tet.2005.06.080

  日期：2005.10

  mediate the Stille coupling of allylic and benzylic halides with alkenyl, aryl and allyl stannanes. In competition experiments between 4-nitrobromobenzene and benzyl bromide with a cis-stannylvinyl ester, (Ph3P)2Pd(N-Succ)Br preferentially cross-couples benzyl bromide, whereas with other commonly employed precatalysts 4-nitrobromobenzene undergoes preferential cross-coupling. Furthermore, preferential

  已经研究了由空气和湿气稳定的含有琥珀酰亚胺或邻苯二甲酰亚胺（亚氨酸酯）配体的钯（II）膦配合物介导的有机锡烷和有机卤化物的斯蒂勒偶联。已经开发出一种有效的合成路线，以合成几种含有琥珀酰亚胺和邻苯二甲酰亚胺配体的钯（II）配合物。顺式-溴代双（三苯基膦）（N-琥珀酰亚胺）钯（II）[（Ph 3 P）2 Pd（N -Succ）Br]被证明可介导烯丙基和苄基卤化物的Stille偶联与烯基，芳基和烯丙基锡烷。在4-硝基溴苯和苄基溴与顺式-锡烷基乙烯基酯（Ph 3 P）2的竞争实验中Pd（N -Succ）Br优先使苄基溴交联，而与其他常用的预催化剂4-硝基溴苯进行优先交叉偶联。此外，首次观察到失活的苄基溴优先于活化的苄基溴的反应。卤化物的类型和琥珀酰亚胺配体的存在对于有效的Stille偶联至关重要。还显示出膦配体的类型改变了钯（II）琥珀酰亚胺配合物的催化活性。
• Visible Light Induced Brønsted Acid Assisted Pd‐Catalyzed Alkyl Heck Reaction of Diazo Compounds and <i>N</i> ‐Tosylhydrazones
  作者：Ziyan Zhang、Nikita Kvasovs、Anastasiia Dubrovina、Vladimir Gevorgyan

  DOI：10.1002/anie.202110924

  日期：2022.1.3

  mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. This method features Brønsted acid assisted generation of hybrid palladium C(sp3)-centered radical intermediate and broad reaction scope, highlighting the diverse applicability and the potential utility of this protocol in late-stage functionalization.

  报道了重氮化合物和N-甲苯磺酰腙的温和可见光诱导的钯催化烷基 Heck 反应。该方法具有布朗斯台德酸辅助生成杂化钯C(sp 3 )中心自由基中间体和广泛的反应范围，突出了该方案在后期功能化中的多样化适用性和潜在效用。
• Common precursor strategy for the synthesis of bestatin, amprenavir intermediate and syn-4-hydroxy-5-phenyl-γ-lactam
  作者：Brijesh Kumar、Mushtaq A. Aga、Abdul Rouf、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1039/c4ra00205a

  日期：——

  A synthetic strategy using α,β-unsaturated ester as a common precursor for the preparation of bestatin hydrochloride, an anticancer agent; 1,3-diaminoalcohol, an amprenavir intermediate andsyn-4-hydroxy-5-phenyl-γ-lactam, an intermediate of bioactive molecules with good yields and excellent stereoselectivity is described.

  使用α,β-不饱和酯作为通用前驱体，用于合成抗癌药物贝塔斯汀盐酸盐、阿普那韦中间体1,3-二氨基醇和具有良好收率和优秀立体选择性的生物活性分子中间体syn-4-羟基-5-苯基-γ-内酰胺的策略被描述。
• Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2<i>H</i>-Azirines
  作者：Nicole S. Y. Loy、Alok Singh、Xianxiu Xu、Cheol-Min Park

  DOI：10.1002/anie.201209301

  日期：2013.2.18

  a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropionic acid). The formation of the key intermediate is catalyst‐controlled, and subsequent cyclization and oxidation affords pyridines in excellent yields. The method has been used for the efficient synthesis of polyarylpyridines.

  漫游范围：使用温和的反应条件（参见方案； esp =α，α，α'，α'-四甲基-1,3-苯二丙酸），标题反应可耐受吡啶环上的大量取代基。关键中间体的形成受催化剂控制，随后的环化和氧化反应使吡啶具有优异的收率。该方法已用于有效合成聚芳基吡啶。
• Ni-catalyzed reductive coupling of α-halocarbonyl derivatives with vinyl bromides
  作者：Canbin Qiu、Ken Yao、Xinghua Zhang、Hegui Gong

  DOI：10.1039/c6ob02269c

  日期：——

  This work describes the vinylation of α-halo carbonyl compounds with vinyl bromides under Ni-catalyzed reductive coupling conditions. While aryl-conjugated vinyl bromides entail pyridine as the sole labile ligand, the alkyl-substituted vinyl bromides require both bipyridine and pyridine as the co-ligands.

  这项工作描述了在镍催化的还原偶联条件下，α-卤代羰基化合物与乙烯基溴的乙烯基化。芳基共轭乙烯基溴化物需要吡啶作为唯一的不稳定配体，而烷基取代的乙烯基溴化物则需要联吡啶和吡啶作为共配体。