2-氧代-4-苯基丁酸乙酯 | 64920-29-2

• 物质功能分类: 原料药 - 血液系统用药 - 止血药
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-氧代-4-苯基丁酸乙酯
• 中文别名: 2-羰基-4-苯基丁酸乙酯；2-氧-4-苯基丁酸乙酯；2-氧代苯丁酸乙酯；α-氧代苯丁酸乙酯；2-氧代-基丁酸乙酯；2-氧代-4-苯基丁酸乙酯,EOPB；纤维蛋白；EOPB
• 英文名称: 2-oxo-4-phenylbutanoic acid ethyl ester
• 英文别名: Ethyl 2-oxo-4-phenylbutyrate；ethyl 2-oxo-4-phenylbutanoate
• CAS: 64920-29-2
• 化学式: C₁₂H₁₄O₃
• mdl: MFCD00037533
• 分子量: 206.241
• InChiKey: STPXIOGYOLJXMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  132 °C/2 mmHg (lit.)
• 密度：
  1.091 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 稳定性/保质期：

  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S23,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2918300090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放在密封容器中，并放置在阴凉、干燥处。请确保储存位置远离氧化剂。

SDS

Name:	Ethyl 2-oxo-4-phenylbutyrate 97% Material Safety Data Sheet
Synonym:
CAS:	64920-29-2

Section 1 - Chemical Product MSDS Name:Ethyl 2-oxo-4-phenylbutyrate 97% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
64920-29-2	Ethyl 2-oxo-4-phenylbutyrate	97%	265-276-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

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

---

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.
Notes to Physician:

---

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.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

---

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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 64920-29-2: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 241 deg C @ 760 mmH
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.091
Molecular Formula: C12H14O3
Molecular Weight: 206.0962

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 64920-29-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-oxo-4-phenylbutyrate - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 64920-29-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 64920-29-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 64920-29-2 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：

• 用于有机合成中间体和药物中间体
• 作为有机中间体
• 是赖诺普利的中间体

反应信息

• 作为反应物：
  描述：

  2-氧代-4-苯基丁酸乙酯 在 镍 盐酸 、 氰基磷酸二乙酯 、 3 A molecular sieve 、 氢溴酸 、 氢气 、 sodium acetate 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 盐酸地拉普利
  参考文献：
  名称：

  N- [N-[（S）-1-乙氧基羰基-3-苯基丙基] -L-丙氨酰] -N-（茚满-2-基）甘氨酸（CV-3317）的设计与合成酶抑制剂。

  摘要：

  一种新的血管紧张素转换酶（ACE）抑制剂N-[N-[(S)-1-乙氧基碳基-3-苯基丙基]-L-丙氨酸]-N-(茚-2-基)甘氨酸（9a）是在对ACE抑制剂中C端氨基酸部分的结构要求进行广泛研究后发现的。本文描述了9a的合成及其绝对构型的确定。

  DOI：

  10.1248/cpb.34.2852
• 作为产物：
  描述：

  3-苯丙酸乙酯 在 硫酸 、 sodium methylate 作用下， 以 乙醇 、 硫酸 为溶剂， 反应 21.5h， 生成 2-氧代-4-苯基丁酸乙酯
  参考文献：
  名称：

  Synthesis and angiotensin converting enzyme inhibitory activity of 1,5-benzothiazepine and 1,5-benzoxazepine derivatives. I.

  摘要：

  新型血管紧张素转化酶（ACE）抑制剂的设计与合成，包括(R)-3-氨基-4-氧代-2, 3, 4, 5-四氢-1, 5-苯硫氮杂环-5-乙酸（7, 26, 33 和 37）以及(S)-3-氨基-4-氧代-2, 3, 4, 5-四氢-1, 5-苯氧氮杂环-5-乙酸（8 和 27），本文进行了描述。这些系列中的一些化合物在体外和体内显示出强烈的ACE抑制活性。同时讨论了结构-活性关系。

  DOI：

  10.1248/cpb.34.1128

文献信息

• Methodology Development in Directed Evolution: Exploring Options when Applying Triple-Code Saturation Mutagenesis
  作者：Ge Qu、Richard Lonsdale、Peiyuan Yao、Guangyue Li、Beibei Liu、Manfred T. Reetz、Zhoutong Sun

  DOI：10.1002/cbic.201700562

  日期：2018.2.2

  Directed evolution: Two strategies regarding the application of triple‐code saturation mutagenesis (TCSM) at multiresidue sites of the T. brockii alcohol dehydrogenase (TbSADH) by using distinct reduced amino‐acid alphabets are compared. By using prochiral tetrahydrofuran‐3‐one, highly R‐ and S‐selective variants are obtained with minimal screening. The origin of stereoselectivity is provided by molecular

  定向进化：关于三重码饱和诱变（TCSM）的在所述的多残留部位应用的两种策略布氏热厌氧杆菌醇脱氢酶（TbSADH）通过使用不同的减小的氨基酸字母进行比较。通过使用前手性四氢呋喃-3-酮，只需很少的筛选即可获得高度R和S选择性的变体。立体选择性的起源是由分子动力学模拟提供的。
• A genomic search approach to identify carbonyl reductases in <i>Gluconobacter oxydans</i> for enantioselective reduction of ketones
  作者：Rong Chen、Xu Liu、Jinping Lin、Dongzhi Wei

  DOI：10.1080/09168451.2014.925775

  日期：2014.8.3

  The versatile carbonyl reductases from Gluconobacter oxydans in the enantioselective reduction of ketones to the corresponding alcohols were exploited by genome search approach. All purified enzymes showed activities toward the tested ketoesters with different activities. In the reduction of 4-phenyl-2-butanone with in situ NAD(P)H regeneration system, (S)-alcohol was obtained with an e.e. of up to 100% catalyzed by Gox0644. Under the same experimental condition, all enzymes catalyzed ethyl 4-chloroacetoacetate to give chiral products with an excellent e.e. of up to 99%, except Gox0644. Gox2036 had a strict requirement for NADH as the cofactor and showed excellent enantiospecificity in the synthesis of ethyl (R)-4-chloro-3-hydroxybutanoate. For the reduction of ethyl 2-oxo-4-phenylbutyrate, excellent e.e. (&gt;99%) and high conversion (93.1%) were obtained by Gox0525, whereas the other enzymes showed relatively lower e.e. and conversions. Among them, Gox2036 and Gox0525 showed potentials in the synthesis of chiral alcohols as useful biocatalysts.

  通过基因组搜索方法，利用Gluconobacter oxydans中多功能醛酮还原酶对酮类化合物进行对映选择性还原，获得了一系列酶。所有纯化的酶对不同活性的酮酯表现出活性。在使用原位NAD(P)H再生系统还原4-苯基-2-丁酮时，Gox0644催化得到了e.e.高达100%的(S)-醇。在相同的实验条件下，除Gox0644外，所有酶均催化乙酸乙酯4-氯乙酮酸酯生成具有高达99%的优异e.e.的手性产物。Gox2036对NADH作为辅因子有严格要求，在合成乙酸(R)-4-氯-3-羟基丁酸乙酯中表现出优异的对映选择性。在还原乙酸2-氧代-4-苯基丁酸酯时，Gox0525获得了优异的e.e.（&gt;99%）和高转化率（93.1%），而其他酶则表现出相对较低的e.e.和转化率。其中，Gox2036和Gox0525在合成手性醇作为有用的生物催化剂方面表现出潜力。

• Efficient α-Methylenation of Carbonyl Compounds in Ionic Liquids at Room Temperature
  作者：J. Rodrigues、Juliana Vale、Daniel Zanchetta、Paulo Moran

  DOI：10.1055/s-0028-1087389

  日期：——

  The application of several 1-butyl-3-methylimidazolium (BMIM) salt ionic liquids as solvent in the α-methylenation of carbonyl compounds at room temperature is reported. The ionic liquid [BMIM][NTf2] gave a clean reaction in a short time and good yields of several α-methylene carbonyl compounds. This ionic liquid was reused without affecting the reaction rates or yields over seven runs.

  报道了几种1-丁基-3-甲基咪唑鎓（BMIM）盐离子液体在常温下对羰基化合物进行α-亚甲基化的溶剂应用。离子液体[BMIM][NTf2]在短时间内提供了干净的反应和多种α-亚甲基羰基化合物的高产率。这种离子液体在连续七次使用中重复使用，未影响反应速率或产率。
• Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
  作者：Zechao Lin、Jiahong Li、Qingfei Huang、Qiuya Huang、Qiwei Wang、Lei Tang、Deying Gong、Jun Yang、Jin Zhu、Jingen Deng

  DOI：10.1021/acs.joc.5b00241

  日期：2015.5.1

  ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π

  设计并合成了一系列两亲性配体。具有配体的铑配合物被用于纯水中宽范围的长链脂族酮酸酯的不对称转移氢化。使用手性表面活性剂型催化剂2观察到α-，β-，γ-，δ-和ε-酮酸酯以及α-和β-酰氧基酮的定量转化率和出色的对映选择性（高达99％ee）。在金属硅油核中，催化剂与底物之间的长脂肪链之间的CH /π相互作用和长脂肪链的强疏水相互作用在催化过渡态中起着关键作用。胶束中金属催化位点与核心的疏水微环境之间的协同作用有助于实现高立体选择性。
• Method for homogeneous enantioselective hydrogenation using catalytic ferrocenyl bis-phosphine complexes
  申请人：Degussa-Huls AG

  公开号：US06348620B1

  公开（公告）日：2002-02-19

  The present invention is relative to a method for the homogeneous, catalytic, enantioselective hydrogenation of compounds of the general formula (I) with the aid of compounds of the general formula (II) The use of the hydrogenated derivatives in organic synthesis.

  本发明涉及一种用于对一般式（I）化合物进行均相、催化、对映选择性氢化的方法，借助一般式（II）化合物。利用氢化衍生物在有机合成中的应用。

表征谱图