β-羟基苯丙酸乙酯 | 5764-85-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: β-羟基苯丙酸乙酯
• 中文别名: 3-羟基-3-丙酸乙酯；3-羟基-3-苯基丙酸乙酯；-羟基苯丙酸乙酯
• 英文名称: Ethyl 3-hydroxy-3-phenylpropanoate
• 英文别名: ethyl mandelate
• CAS: 5764-85-2
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD00086891
• 分子量: 194.23
• InChiKey: DVIBDQWVFHDBOP-UHFFFAOYSA-N

物化性质

• 沸点：
  154-156 °C(Press: 13 Torr)
• 密度：
  1.119
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• LogP：
  1.462 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 海关编码：
  2918199090
• 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 3-hydroxy-3-phenylpropanoate
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 3-hydroxy-3-phenylpropanoate
CAS number: 5764-85-2

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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: C11H14O3
Molecular weight: 194.2

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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：

  β-羟基苯丙酸乙酯 在 三甲基氯硅烷 、 乙腈 、 sodium iodide 作用下， 以 正己烷 为溶剂， 反应 24.0h， 以91%的产率得到3-苯丙酸乙酯
  参考文献：
  名称：

  使用 Me3SiCl-NaI-MeCN 试剂方便地还原去除苄基羟基和三甲基甲硅烷氧基基团

  摘要：

  在室温下，用 6 当量的 Me3SiCl-NaI-MeCN 试剂在己烷中处理，可以还原去除苄基位置的仲羟基和叔羟基。通过向反应体系中加入2当量的水也消除了苄基三甲基甲硅烷氧基。这种还原作用适用于诸如布洛芬、布布芬、萘普生和相关化合物以及 (±)-ar-turmerone（一种有气味的倍半萜烯）等抗炎剂前体的合成。

  DOI：

  10.1246/bcsj.62.3537
• 作为产物：
  描述：

  3-苯基环氧乙烷甲酸乙酯 在 bis(acetylacetonate)nickel(II) 、 三乙基铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 以97%的产率得到β-羟基苯丙酸乙酯
  参考文献：
  名称：

  镍催化氧肟酮的脱氧：环氧化合物转化为烯烃

  摘要：

  在二乙基锌作为脱氧剂存在下，在镍的催化下，环氧化物的脱氧发生，以产生烯烃。在该催化体系中，具有多种取代方式的环氧化合物被脱氧，从而以高收率得到末端的1，1-二取代的，1，2-二取代的，三取代的和四取代的烯烃。我们检查的1,2-二取代环氧化物的反应以E-立体选择性方式进行。还观察到通过该转化与其他官能团的高度相容性。

  DOI：

  10.1016/j.tetlet.2019.151518

文献信息

• Chiral-at-metal iridium complex for efficient enantioselective transfer hydrogenation of ketones
  作者：Cheng Tian、Lei Gong、Eric Meggers

  DOI：10.1039/c6cc00972g

  日期：——

  A bis-cyclometalated iridium(III) complex with metal-centered chirality catalyzes the enantioselective transfer hydrogenation of ketones with high enantioselectivities at low catalyst loadings down to 0.002 mol%. Importantly, the rate of catalysis...

  具有金属中心手性的双环金属化铱（III）络合物在低至0.002 mol％的低催化剂负载下催化具有高对映选择性的酮的对映选择性转移氢化反应。重要的是，催化速率...
• Efficient Water Reduction with sp³ -sp³ Diboron(4) Compounds: Application to Hydrogenations, H-D Exchange Reactions, and Carbonyl Reductions
  作者：Mathias Flinker、Hongfei Yin、René W. Juhl、Espen Z. Eikeland、Jacob Overgaard、Dennis U. Nielsen、Troels Skrydstrup

  DOI：10.1002/anie.201709685

  日期：2017.12.11

  demonstrated by conducting a series of selective reductions of alkynes and alkenes, and hydrogen–deuterium exchange reactions using two‐chamber reactors. Finally, as the water reduction reaction generates an intermediate borohydride species, a range of aldehydes and ketones were reduced by using water as the hydride source.

  合成了一系列结晶的sp 3 -sp 3 diboron（4）化合物，它们显示出促进形成二氢的水的简便还原。通过对乙炔和烯烃进行一系列的选择性还原，以及使用两室反应器进行氢-氘交换反应，证明了这些二硼作为简单有效的二氢和二氘源的应用。最后，由于水还原反应生成了中间的硼氢化物，通过使用水作为氢化物源，可以还原一系列醛和酮。
• [EN] CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE LA CÉRAMIDE GALACTOSYLTRANSFÉRASE POUR LE TRAITEMENT DE MALADIES
  申请人：BIOMARIN PHARM INC

  公开号：WO2017214505A1

  公开（公告）日：2017-12-14

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物、以及使用这种化合物治疗或预防与酶神经鞘糖脂转移酶（CGT）相关的疾病或紊乱的方法，例如溶酶体贮积症。溶酶体贮积症的例子包括 Krabbe 病和白质变性白血病。
• InCl₃/Me₃SiBr-Catalyzed Direct Coupling between Silyl Ethers and Enol Acetates
  作者：Yoshiharu Onishi、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol200875m

  日期：2011.5.20

  A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.

  InCl 3和Me 3 SiBr的路易斯酸催化剂的组合促进了烯醇乙酸酯在与低反应性甲硅烷基醚的偶联中的直接使用，其中包括酮和醛的官能团得以幸存。也可使用受阻位的甲硅烷基醚，如ROSiEt 3，ROSiPh 3，ROSi t- BuMe 2和ROSi i- Pr 3。
• KB₃H₈: an environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols
  作者：Xinying Li、Tongge Mi、Wenjing Guo、Zhongrui Ruan、Yu Guo、Yan-Na Ma、Xuenian Chen

  DOI：10.1039/d1cc05638g

  日期：——

  Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters.

  首次在空气气氛下探索了在水和 THF 中使用 KB 3 H 8选择性还原醛和酮为其相应的醇，KB 3 H 8是一种空气和湿气稳定、无毒且易于处理的试剂。对照实验表明 KB 3 H 8优于 NaBH 4用于还原 4-乙酰苯甲醛和芳香酮酯的良好选择性。