2-苯基丙烯酸甲酯 | 1865-29-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苯基丙烯酸甲酯
• 英文名称: 2-phenyl-acrylic acid methyl ester
• 英文别名: methyl 2-phenylacrylate；methyl 2-phenylprop-2-enoate
• CAS: 1865-29-8
• 化学式: C₁₀H₁₀O₂
• mdl: MFCD09032492
• 分子量: 162.188
• InChiKey: GQTXKEVAUZYHGE-UHFFFAOYSA-N

物化性质

• 沸点：
  95-98 °C(Press: 6 Torr)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -20°C储存，采用惰性气体保护。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-phenylacrylate
Synonyms: 2-Phenyl-acrylic acid methyl ester

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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: Methyl 2-phenylacrylate
CAS number: 1865-29-8

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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: C10H10O2
Molecular weight: 162.2

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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：

  2-苯基丙烯酸甲酯 在 盐酸 、 silver fluoride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 40.5h， 生成 1-Benzyl-3-phenyl-pyrrolidine-3-carboxylic acid dimethylamide
  参考文献：
  名称：

  新型喹诺酮类抗菌剂。7-（3,3-或3,4-二取代-1-吡咯烷基）喹啉-3-羧酸的合成及生物活性。

  摘要：

  合成了一系列7-（3-氨基-或3-氨基甲基-1-吡咯烷基）-1-环丙基-6,8-二氟-1,4-二氢-4-邻xo-3-喹啉羧酸，并进行了测试抗菌活性。这些喹诺酮的独特之处是吡咯烷环中存在甲基或苯基。尽管这些药物的体外活性通常等于或小于其未取代的对应物，但一种喹诺酮7- [3-（氨基甲基）-3-甲基-1-吡咯烷基] -1-环丙基-6,8-二氟-1,4-二氢-4-氧代-3-喹啉羧酸，在体外和体内均显示出非凡的效力，尤其是针对革兰氏阳性生物。

  DOI：

  10.1021/jm00164a060
• 作为产物：
  描述：

  Alpha-羟甲基苯乙酸甲酯 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以60%的产率得到2-苯基丙烯酸甲酯
  参考文献：
  名称：

  一种吡咯烷类整合素调节剂及其用途

  摘要：

  本发明涉及一种式I所示的化合物及其消旋体、立体异构体、互变异构体、同位素标记物、氮氧化物、溶剂化物、多晶型物、代谢产物、酯、前药或其药学上可接受的盐，以及包含其的药物组合物，其制备方法，及其医药用途，所述式I结构如下：

  公开号：

  CN113354635B
• 作为试剂：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 过氧化双月桂酰 在 iron(II) triflate 、 叠氮基三甲基硅烷 、 2-苯基丙烯酸甲酯 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以72%的产率得到2,2,6,6-tetramethyl-1-(undecyloxy)piperidine
  参考文献：
  名称：

  铁催化过氧化二酰基和TMSN 3催化1,1-二取代烯烃的烷基化

  摘要：

  报道了缺电子烯烃的铁催化的自由基烷基叠氮化。烷基二酰基过氧化物充当烷基源，三甲基甲硅烷基叠氮化物充当叠氮基储库。该方法的特点是反应条件温和，底物范围宽，官能团耐受性好，可以高产率提供各种α-叠氮基酯，α-叠氮基酮和α-叠氮基氰化物。这些叠氮化物可以容易地转移成多种氨基酸衍生物。

  DOI：

  10.1021/acs.orglett.0c00969

文献信息

• An approach to spirooxindoles via palladium-catalyzed remote C–H activation and dual alkylation with CH₂Br₂
  作者：Changdong Shao、Zhuo Wu、Xiaoming Ji、Bo Zhou、Yanghui Zhang

  DOI：10.1039/c7cc06196j

  日期：——

  A facile and efficient approach for the synthesis of spirooxindoles has been developed via the coupling of spirocyclic C, C-palladacycles with CH2Br2. The key spirocyclic palladacycles are generated catalytically via intramolecular remote C–H activation. A range of spirooxindoles can be synthesized in good to excellent yields from readily available starting materials.

  通过螺环C，C-palladacycles与CH2Br2的耦合，已开发出一种简便高效的合成螺硫辛多酯的方法。关键的螺环戊四环是通过分子内远程C–H活化催化生成的。可以从容易获得的起始原料中以良好至极好的产率合成一系列螺硫醇。
• Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin
  作者：Lingling Chu、Chisa Ohta、Zhiwei Zuo、David W. C. MacMillan

  DOI：10.1021/ja505964r

  日期：2014.8.6

  carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, α-oxy, and α-amino acids, provides a versatile CO2-extrusion platform to generate Michael donors without the requirement for organometallic activation or propagation

  羧酸作为自由基迈克尔加成的无痕活化基团的直接应用是通过可见光介导的光氧化还原催化实现的。光子诱导氧化一系列广泛的羧酸，包括碳氢化合物取代的、α-氧基和 α-氨基酸，提供了一个多功能的 CO2 挤出平台来生成迈克尔供体，而无需有机金属活化或传播。多种迈克尔受体适用于这种新的共轭加成策略。还介绍了该技术在药物普瑞巴林（由辉瑞以商品名 Lyrica 商业化）的三步合成中的应用。
• Scaffold-Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin-3,2′-oxindoles] with Structural Diversity through Catalytic Isatin-Derived 1,3-Dipolar Cycloadditions
  作者：Feng Shi、Zhong-Lin Tao、Shi-Wei Luo、Shu-Jiang Tu、Liu-Zhu Gong

  DOI：10.1002/chem.201200358

  日期：2012.5.29

  Catalytic asymmetric construction of the biologically important spiro[pyrrolidin‐3,2′‐oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee) has been established by using an organocatalytic 1,3‐dipolar cycloaddition of isatin‐based azomethine ylides. This protocol represents the first example of catalytic asymmetric 1,3‐dipolar

  通过使用有机催化1,3，已经建立了具有重要立体选择性（具有高达99：1 dr，98％ee的连续性）的具有重要季螺立体构象中心的重要生物学螺旋[pyrrolidin-3,2'-oxindole]支架的催化不对称结构。 基于靛红的甲亚胺烷基化物的偶极环加成。该方案代表了催化不对称1,3-偶极环加成反应的第一个例子，涉及不对称环酮就地生成的甲亚胺基化物。另外，对反应的过渡态进行了理论计算以了解立体化学。使用这些螺[吡咯烷酮-3,2'-羟吲哚]的初步生物测定显示，几种化合物对SW116细胞显示中等程度的细胞毒性。
• Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters
  作者：Alistair J. M. Farley、Christopher Sandford、Darren J. Dixon

  DOI：10.1021/jacs.5b10226

  日期：2015.12.30

  The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described. The strong Brønsted basicity of the iminophosphorane moiety of the catalyst provides the necessary activation of the alkyl thiol pro-nucleophile, while the two tert-leucine residues flanking a

  描述了在温和条件下由双功能亚氨基正膦有机催化剂催化的烷基硫醇与未活化的 α-取代丙烯酸酯的高度对映选择性磺基-迈克尔加成反应。催化剂亚氨基正膦部分的强布朗斯台德碱性为烷基硫醇亲核试剂提供了必要的活化，而中央硫脲氢键供体侧翼的两个叔亮氨酸残基促进了瞬态烯醇中间体质子化过程中的高对映选择性. 该反应在烷基硫醇、酯部分和 α,β-不饱和酯的 α-取代基方面的范围很广，以优异的产率（高达 >99%）和对映选择性（高达到 96% ee)，并且可以使用低至 0 的催化剂负载量进行十克放大。
• Cyanomethyl anion transfer reagents for diastereoselective Corey–Chaykovsky cyclopropanation reactions
  作者：Renè Hommelsheim、Katharina J. Hock、Christian Schumacher、Mohanad A. Hussein、Thanh V. Nguyen、Rene M. Koenigs

  DOI：10.1039/c8cc05602a

  日期：——

  A readily available and bench-stable cyanomethyl sulfonium salt was used in highly diastereoselective Corey–Chaykovsky cyclopropanation reactions of electron-poor olefins. This efficient method provides a rapid route to access densely functionalized cyclopropyl nitriles.

  一种易于获得且稳定的氰基甲基methyl盐被用于高度非对映选择性的电子贫烯烃的Corey-Chaykovsky环丙烷化反应中。这种有效的方法提供了一种快速途径来获取致密的官能化环丙基腈。