(S)-(-)-3-羟基-3-苯基丙酸乙酯 | 33401-74-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: (S)-(-)-3-羟基-3-苯基丙酸乙酯
• 中文别名: (S)-3-羟基-3-苯基丙酸乙酯；(S)-3-羟基-3-苯丙酸乙酯
• 英文名称: ethyl (3R)-3-hydroxy-3-phenylpropionate
• 英文别名: ethyl (S)-3-hydroxy-3-phenylpropanoate；(S)-Ethyl 3-Hydroxy-3-phenylpropanoate；ethyl (3S)-3-hydroxy-3-phenylpropanoate
• CAS: 33401-74-0
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD00216721
• 分子量: 194.23
• InChiKey: DVIBDQWVFHDBOP-JTQLQIEISA-N

物化性质

• 沸点：
  195 °C(Press: 11 Torr)
• 密度：
  1.51g/ml
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

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

• 安全说明：
  S24/25,S26,S37/39
• WGK Germany：
  3
• 海关编码：
  29155000
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存放在阴凉干燥处。

SDS

Name:	(-)-Ethyl (S)-3-hydroxy-3-phenylpropionate Material Safety Data Sheet
Synonym:
CAS:	33401-74-0

Section 1 - Chemical Product MSDS Name:(-)-Ethyl (S)-3-hydroxy-3-phenylpropionate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33401-74-0	(-)-Ethyl (S)-3-hydroxy-3-phenylpropio		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 33401-74-0: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H14O3
Molecular Weight: 194.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 33401-74-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-Ethyl (S)-3-hydroxy-3-phenylpropionate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 33401-74-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33401-74-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33401-74-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-(-)-3-羟基-3-苯基丙酸乙酯 在 盐酸 、 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 反应 6.5h， 生成 (3S)-N-甲基-3-苯基-3-[4-(三氟甲基)苯氧基]-1-丙胺盐酸盐(1:1)
  参考文献：
  名称：

  通过微生物还原苯甲酰乙酸乙酯对氟西汀的两种对映异构体进行不对称合成

  摘要：

  通过面包酵母（Saccharomyces cerevisiae），球孢白僵菌或白色念珠菌的微生物还原，可以高光学收率得到（S）-3-羟基-3-苯基丙酸乙酯。该对映体纯的醇被转化为氟西汀的两种对映体（7）。面包师减少酵母所产生的产品的ee值（87–93％）低于早期研究中错误归因于100％的值。

  DOI：

  10.1016/s0040-4020(01)89866-5
• 作为产物：
  描述：

  3-羟基-3-苯丙酸 在 吡啶 、 盐酸 、 乙醇 、 sodium nitrite 作用下， 生成 (S)-(-)-3-羟基-3-苯基丙酸乙酯
  参考文献：
  名称：

  所述的397.瓦尔登翻转反应p -toluenesulphinic和p乙基甲苯磺酸酯d -β羟基-β-苯基

  摘要：

  DOI：

  10.1039/jr9350001663
• 作为试剂：
  描述：

  、 、 苯甲酰乙酸乙酯 、 在 N,N-二甲基甲酰胺 、 氮 、 氢气 、 乙醚 、 水 、 氯化钠 、 Sodium sulfate-III 、 silica gel 、 (S)-(-)-3-羟基-3-苯基丙酸乙酯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0~100.0 ℃ 、270.18 MPa 条件下， 反应 24.17h， 以to give the title compound, ethyl (S)-3-hydroxy-3-phenylpropionate的产率得到(S)-(-)-3-羟基-3-苯基丙酸乙酯
  参考文献：
  名称：

  Process of preparing optically active β-hydroxycarboxylic acid derivative

  摘要：

  本发明公开了一种制备光学活性β-羟基羧酸衍生物的方法，包括在具有2,3-双(二烷基膦)吡嗪衍生物配体的过渡金属配合物催化剂存在下不对称氢化β-酮化合物。偏噻唑衍生物优选为喹哌衍生物，过渡金属优选为钌。优选的偏噻唑衍生物示例包括(S,S)-2,3-双(叔丁基甲基膦基)喹哌、(R,R)-双(叔丁基甲基膦基)喹哌、(S,S)-双(叔-金刚烷甲基膦基)喹哌和(R,R)-双(金刚烷甲基膦基)喹哌。

  公开号：

  US07649117B2

文献信息

• RhIII- and IrIII-Catalyzed Asymmetric Transfer Hydrogenation of Ketones in Water
  作者：Xiaofeng Wu、Xiaohong Li、Antonio Zanotti-Gerosa、Allan Pettman、Jianke Liu、Allan James Mills、Jianliang Xiao

  DOI：10.1002/chem.200701258

  日期：2008.2.27

  formate in neat water is shown to be viable with Rh-TsDPEN and Ir-TsDPEN catalysts, derived in situ from [Cp*MCl2]2 (M=Rh, Ir) and TsDPEN. A variety of ketones were reduced, including nonfunctionalized aryl ketones, heteroaryl ketones, ketoesters, and unsaturated ketones. In comparison with Ir-TsDPEN and the related Ru II catalyst, the Rh III catalyst is most efficient in water, affording enantioselectivities

  研究表明，纯净水中甲酸酯在酮中的不对称转移氢化（ATH）在Rh-TsDPEN和Ir-TsDPEN催化剂上是可行的，该催化剂原位衍生自[Cp * MCl2] 2（M = Rh，Ir）和TsDPEN。还原了多种酮，包括未官能化的芳基酮，杂芳基酮，酮酸酯和不饱和酮。与Ir-TsDPEN和相关的Ru II催化剂相比，Rh III催化剂在水中的效率最高，即使在100-1000的底物/催化剂（S / C）比下，对映选择性高达99％ee。惰性气氛。水相还原显示出高度依赖pH值；对于Rh-和Ir-TsDPEN，TOF大于50 mol mol（-1）h（-1）的最佳pH窗口分别为5.5-10.0和6.5-8.5。在pH窗口之外，根据pH的不同，还原速度会变慢或停滞。但是，对映选择性仅在酸性条件下会腐蚀。在较高的S / C比下，Rh-TsDPEN的ATH水溶液显示出对产物以及副产物的抑制作用。产物抑制似乎至少
• A bifunctionalized organic–inorganic hybrid silica: synergistic effect enhances enantioselectivity
  作者：Wei Xiao、Ronghua Jin、Tanyu Cheng、Daquan Xia、Hui Yao、Fei Gao、Boxin Deng、Guohua Liu

  DOI：10.1039/c2cc36350j

  日期：——

  An imidazolium-based bifunctional heterogeneous catalyst exhibits excellent catalytic efficiency in asymmetric transfer hydrogenation of aromatic ketones in aqueous medium. The superior catalytic performance and the enhanced enantioselectivity is attributed to the synergistic effect of salient imidazolium phase-transfer function and the confined nature of the chiral organoiridium catalyst.

  一种基于咪唑鎓的双功能非均相催化剂在水介质中表现出优异的芳香酮不对称转移氢化催化效率。其卓越的催化性能和提高的立体选择性归因于显著的咪唑鎓相转移功能和受限的手性有机铱催化剂之间的协同效应。
• 2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene:  A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis
  作者：Tiziana Benincori、Edoardo Cesarotti、Oreste Piccolo、Franco Sannicolò

  DOI：10.1021/jo991533x

  日期：2000.4.1

  C2-symmetry chelating ligand for transition metals, is described, starting from 2,5-dimethylthiophene. The complexes of this electron-rich diphosphine with Ru(II) and Rh(I) were used as catalysts in some homogeneous hydrogenation reactions of prostereogenic carbonyl functions of alpha- and beta-ketoesters, of prostereogenic carbon-carbon double bonds of substituted acrylic acids, and of N-acetylenamino

  对映纯（+）-和（-）-2,2'，5,5'-四甲基-4,4'-双-（二苯基膦基）-3,3'-联噻吩（tetraMe-BITIOP的四步直接合成），描述了一种新的C2对称的过渡金属螯合配体，从2,5-二甲基噻吩开始。这种富电子的二膦与Ru（II）和Rh（I）的配合物在α-和β-酮酸酯的酯基羰基官能团，取代丙烯酸的酯基碳-碳双键的均相加氢反应中用作催化剂和N-乙酰基氨基酸。发现在所有实验中对映体过量都非常好，并且与文献报道的在相同实验条件下进行的相同反应的最佳结果相当，
• Practical asymmetric hydrogenation of β-keto esters at atmospheric pressure using chiral Ru (II) catalysts
  作者：J.P. Genêt、V. Ratovelomanana-Vidal、M.C. Caño de Andrade、X. Pfister、P. Guerreiro、J.Y. Lenoir

  DOI：10.1016/0040-4039(95)00873-b

  日期：1995.7

  conditions of asymmetric hydrogenation of β-keto esters with chiral Ru(II) catalysts are described. It is now possible to carry out the reaction at atmospheric pressure. Under these conditions, β-keto esters are hydrogenated to β-hydroxy esters with excellent enantiomeric excesses (up to 99%) using chiral ruthenium (II) catalysts easily prepared in situ by treatment of commercially available (COD)Ru(2-methylallyl)2

  描述了使用手性Ru（II）催化剂不对称氢化β-酮酯的新实用条件。现在可以在大气压下进行反应。在这些条件下，使用手性钌（II）催化剂，通过处理可商购的（COD）Ru（2-甲基烯丙基）即可轻松制得具有出色对映体过量（至多99％）的β-酮酸酯，氢化成β-羟基酯。2在适当的手性配体例如Binap，MeO-Biphep和Me-Duphos的存在下。
• A chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal from ethyl 1,3-dithiolane-2-carboxylate. Synthesis of acetate aldols in high enantiomeric purity
  作者：Syun-ichi Kiyooka、Mostofa Abu Hena

  DOI：10.1016/0957-4166(96)00265-0

  日期：1996.8

  Asymmetric synthesis of dithiolane aldols 3 was achieved in good yields by using silyl ketene acetal 1, derived from ethyl 1,3-dithiolane-2-carboxylate, in the chiral oxazaborolidinone (L-1 and D-2)-promoted aldol reaction and desulfurization of 3 resulted in production of acetate aldols 4 in high enantiomerc purity.

  在手性草并硼杂硼烷酮（L-1和D-2）促进的醛醇缩合反应和脱硫反应中，通过使用由1,3-二硫杂环戊酸-2-羧酸乙酯衍生的甲硅烷基乙烯酮缩醛1，可以高收率获得二硫杂环戊烷醛3的不对称合成。的3导致生产乙酸醛醇的4在高纯度enantiomerc。