CAS: 94-02-0; Ethyl 3-Oxo-3-Phenylpropanoate

该化合物是一种多用途有机化合物,具有多种好处,其化学稳定性和对水解的耐受性很高,因此适合于香水,香味和药品生产的各种应用,此外,其芳香特性有助于其作为溶剂和有机合成反应中间剂的用途.

英文名称Ethyl 3-Oxo-3-Phenylpropanoate
中文名称3-氧代-3-苯基丙酸乙酯
IUPAC名称ethyl 3-oxo-3-phenylpropanoate
其它别名苯甲酰乙酸乙酯; 3氧代苯丙酸乙酯; Ethyl Benzoylacetate,(Benzoylacetic Acid Ethyl Ester)
CAS编号94-02-0
MFCD编号:MFCD00009196
EINECS号:202-295-3
FDA UNII编号:K8CHJ4MKM0
分子式:C11H12O3
分子量:192.21
产品CID: 1985398
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
InChIKey: GKKZMYDNDDMXSE-UHFFFAOYSA-N
InChI=1S/C11H12O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3…
计算化学: 氢键受体数3.0氢键供体数0.0可旋转键数4.0

物理性质

熔点<0 °C
沸点268.1°C at 760 mmHg
闪点140°C
密度1.1±0.1 g/cm3
pKa:9.85±0.23(预测)
PSA:43.37
LogP:1.8225
折射率1.509
蒸汽压0.0±0.5 mmHg at 25°C
溶解性Alcohol: Miscible
敏感性光敏感
外观形态棕色粉末
储存条件存储低于 +30°C.
产品应用用于有机合成.
性质描述无色液体.沸点265-270°C(分解),相对密度1.122(15/4°C),折光率1.5338,闪点140°C.能与乙醇,乙醚混溶,不溶于水.能随水蒸气挥发,在空气中和日光下变黄,具有令人愉快的气味.

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2A
严重眼刺激类别2
警示词Warning(警告)
危险描述H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
危险等级IRRITANT
UN编号NONH for all modes of transport
危险品标志Xi
安全声明24/25
危险类别码Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS]
WGK Germany2

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

5764-85-2 = 94-02-0
反应条件:1.1 Reagents: Manganese Oxide (Mno2) (Electrolytic) Solvents: Hexane
标题:Oxidation Of Alcohols With Electrolytic Manganese Dioxide. Its Application For The Synthesis Of Insect Pheromones
作者:Tsuboi,Sadao; Ishii,Naomi; Sakai,Takashi; Tari,Isao; Utaka,Masanori
参考文献:Bulletin Of The Chemical Society Of Japan 日期:1990 卷标:63(7) 页码:1888-93]

2216-94-6 = 94-02-0
反应条件:1.1 Reagents: 4-Methylbenzaldehyde Oxime Solvents: Dimethylformamide; 3 H,100 °C
标题:Base-Promoted Difunctionalization Of Alkynes: One-Pot Synthesis Of Polysubstituted Chromones+
作者:Wang,Mengdan; Cheng,Lu; Ma,Junying; Lu,Weiwei; Wang,Junling
参考文献:European Journal Of Organic Chemistry 日期:2023 卷标:26(32)]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; Overnight,70 °C; 70 °C -> Rt1.2 Solvents: Water; Cooled
标题:The Construction Of Chiral 3-Acyl Bicyclolactams Via A Ruphox/pd Catalyzed Asymmetric Allylic Substitution Cascade Of α-Carbonylamides
作者:Dong,Siqi; Xu,Shaofeng; Zou,Yashi; Li,Zhaodi; Xu,Kai; Et Al
参考文献:Organic Chemistry Frontiers 日期:2023 卷标:10(7) 页码:1731-1737]

6148-64-7 + 98-88-4 = 94-02-0
反应条件:1.1 Reagents: Triethylamine,Magnesium Chloride Solvents: Acetonitrile1.2 -
标题:A Safe,Economical Method For The Preparation Of β-Oxo Esters
作者:Clay,Ronald J.; Collom,Thomas A.; Karrick,Gregory L.; Wemple,James
参考文献:Synthesis 日期:1993 卷标:(3) 页码:290-2]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Toluene; Rt -> 110 °C1.2 Solvents: Toluene; 10 - 20 Min,110 °C; 110 °C -> Reflux; Reflux -> Rt1.3 Reagents: Acetic Acid; Rt
标题:Electrochemical Oxidative Cyclization: Synthesis Of Polysubstituted Pyrrole From Enamines
作者:Chen,Zhiwei; Shi,Guang; Tang,Wei; Sun,Jie; Wang,Wenxing
参考文献:European Journal Of Organic Chemistry 日期:2021 卷标:2021(6) 页码:951-955]

54882-05-2 = 94-02-0
反应条件:1.1 Reagents: Potassium Fluoride (Aluminum Oxide Supported); 4 Min
标题:Microwave-Assisted β-Elimination Of Sulfoxides On Kf/al2O3 Support Under Solvent-Free Conditions
作者:Moghaddam,Firouz Matloubi; Baradjee,Ghasem Rezanejade
参考文献:Journal Of Sulfur Chemistry 日期:2005 卷标:26(4-5) 页码:325-329]

1028408-98-1 = 94-02-0
反应条件:1.1 Reagents: Hydrogen Peroxide Solvents: Tetrahydrofuran,Water; 1 H,Rt; 2 H,50 °C
标题:A Novel Synthetic Method For β-Keto Esters
作者:Qian,Hao; Ge,Chunrong; Huang,Xian
参考文献:Journal Of Chemical Research 日期:2007 卷标:(3) 页码:160-161]

2216-94-6 = 94-02-0
反应条件:1.1 Catalysts: Silver Triflate,2249872-40-8 Solvents: Methanol; 18.5 H,40 °C
标题:Hydroalkoxylation Of Terminal And Internal Alkynes Catalyzed By Dinuclear Gold(I) Complexes With Bridging Di(N-Heterocyclic Carbene) Ligands
作者:Marcheggiani,Elena; Tubaro,Cristina; Biffis,Andrea; Graiff,Claudia; Baron,Marco
参考文献:Catalysts 日期:2020 卷标:10(1)]

614-20-0 = 94-02-0
反应条件:1.1 Catalysts: Sulfuric Acid Solvents: Ethanol; 15 H,Reflux
标题:Catalytic Reductive Deoxygenation Of Esters To Ethers Driven By Hydrosilane Activation Through Non-Covalent Interactions With A Fluorinated Borate Salt
作者:Rysak,Vincent; Dixit,Ruchi; Trivelli,Xavier; Merle,Nicolas; Agbossou-Niedercorn,Francine; Et Al
参考文献:Catalysis Science & Technology 日期:2020 卷标:10(14) 页码:4586-4592]

141-97-9 + 98-88-4 = 94-02-0
反应条件:1.1 Reagents: Calcium Oxide Solvents: Chloroform; 10 Min,< 5 °C1.2 2 H,< 5 °C; 40 °C; 6 H,40 °C1.3 Catalysts: Sodium Hydroxide; 40 °C -> 62 °C; 4 H,62 °C
标题:Method For Preparing Ethyl Benzoyl Acetate
参考文献:China]

5908-41-8 = 94-02-0
反应条件:1.1 Reagents: Lithium Diisopropylamide Solvents: Tetrahydrofuran; -78 °C; 30 Min,-78 °C1.2 Reagents: Methanol; -78 °C -> 0 °C
标题:An Unusual Dianion Equivalent From Acylsilanes For The Synthesis Of Substituted β-Keto Esters
作者:Galliford,Chris V.; Scheidt,Karl A.
参考文献:Chemical Communications (Cambridge 日期:2008 卷标:(16) 页码:1926-1928]

27262-59-5 = 94-02-0
反应条件:1.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium; 5 H,Rt
标题:Tert-Buok-Catalyzed Condensation Of Ethyl Diazoacetate To Aldehydes And Palladium-Catalyzed 1,2-Hydrogen Migration For The Synthesis Of β-Ketoesters Under Solvent-Free Conditions
作者:Chen,Shufeng; Yuan,Fang; Zhao,Haiying; Li,Baoguo
参考文献:Rsc Advances 日期:2013 卷标:3(31) 页码:12616-12620]

6148-64-7 + 65-85-0 = 94-02-0
反应条件:1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran; 2 H,25 °C1.2 Reagents: 1,1′-Carbonyldiimidazole,Magnesium Chloride Solvents: Tetrahydrofuran; 2 H,25 °C1.3 25 °C1.4 Reagents: Hydrochloric Acid Solvents: Water; 25 °C
标题:Development And Application Of A Solution-Phase Automated Synthesizer,'Chemkonzert'
作者:Machida,Kazuhiro; Hirose,Yoichiro; Fuse,Shinichiro; Sugawara,Tohru; Takahashi,Takashi
参考文献:Chemical & Pharmaceutical Bulletin 日期:2010 卷标:58(1) 页码:87-93]

6148-64-7 + 10364-94-0 = 94-02-0
反应条件:1.1 Reagents: Chlorotrimethylsilane,1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetonitrile1.2 Solvents: Tetrahydrofuran
标题:A Process For The Synthesis Of β-Keto Esters Using In-Situ Generated Trimethylsilyl Malonates
作者:Wang,Xui; Monte,William T.; Napier,James J.; Ghannam,Aneen
参考文献:Tetrahedron Letters 日期:1994 卷标:35(50) 页码:9323-6]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Toluene; Rt -> Reflux; 1 - 2 H,Reflux; 15 - 20 Min,Reflux; Reflux -> Rt1.2 Reagents: Acetic Acid; Rt; Rt
标题:Deoxygenation Of Oximes For The Synthesis Of Pyrrolines Via Hydroimination Cyclization
作者:Han,Wencheng; Liu,Wen-Deng; Su,Junqi; Zhao,Jiannan
参考文献:Organic & Biomolecular Chemistry 日期:2023 卷标:21(16) 页码:3350-3354]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 30 Min,Rt; 15 - 20 Min,Rt -> Reflux; 2 - 3 H,Reflux
标题:Iridium(Iii)-Catalyzed C(3)-H Alkylation Of Isoquinolines Via Metal Carbene Migratory Insertion
作者:Jha,Neha; Singh,Roushan Prakash; Saxena,Paridhi; Kapur,Manmohan
参考文献:Organic Letters 日期:2021 卷标:23(22) 页码:8694-8698]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Toluene; 1 - 2 H,Reflux; 15 - 20 Min,Reflux; Reflux -> Rt1.2 Reagents: Acetic Acid; Rt
标题:Iridium-Catalyzed Enantioselective And Diastereoselective Hydrogenation Of Racemic β'-Keto-β-Amino Esters Via Dynamic Kinetic Resolution
作者:Ling,Fei; Wang,Yifan; Huang,An; Wang,Ze; Wang,Shiliang; Et Al
参考文献:Advanced Synthesis & Catalysis 日期:2021 卷标:363(20) 页码:4714-4719]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; Rt -> Reflux1.2 Solvents: Tetrahydrofuran; Rt; Overnight,Rt1.3 Reagents: Acetic Acid Solvents: Water; Cooled
标题:Preparing Method And Application Of Pyrazoloquinoline Derivative
参考文献:China]

98-86-2 = 94-02-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Toluene; 1 - 2 H,Reflux; 15 - 20 Min,Reflux; Reflux -> Rt1.2 Reagents: Acetic Acid; Rt1.3 Reagents: Water; Cooled
标题:Highly Diastereoselective And Enantioselective Synthesis Of α-Hydroxy β-Amino Acid Derivatives: Lewis Base Catalyzed Hydrosilylation Of α-Acetoxy β-Enamino Esters
作者:Jiang,Yan; Chen,Xing; Zheng,Yongsheng; Xue,Zhouyang; Shu,Chang; Et Al
参考文献:Angewandte Chemie 日期:2011 卷标:50(32) 页码:7304-7307]

100-52-7 = 94-02-0
反应条件:1.1 Catalysts: Tungstate(3-),Tetracosa-μ-Oxododecaoxo[μ12-[phosphato(3-)-Ko:Ko:Ko:Ko′:Ko′:Ko′:... Solvents: Dichloromethane; 2.0 H,Rt
标题:The Silver Salt Of 12-Tungstophosphoric Acid. A Mild And Selective Catalyst For The Synthesis Of β-Ketoesters Via C-H Insertion
作者:Yadav,J. S.; Reddy,B. V. Subba; Purnima,K. V.; Jhansi,S.; Nagaiah,K.; Et Al
参考文献:Catalysis Communications 日期:2008 卷标:9(14) 页码:2361-2364

在 Alkylamine体系中,化学反应生成苯甲酰乙酸乙酯
参考文献:2,2-二氟-4-烷氧基-1,3,2-二氧杂硼烷酮的氨解作用:合成β-酮酰胺和β-烯氨基羧酰胺的途径
标题:2,2-二氟-4-烷氧基-1,3,2-二氧杂硼烷酮的氨解作用:合成β-酮酰胺和β-烯氨基羧酰胺的途径
摘要:4-烷氧基取代的1,3,2-二氧杂硼烷酮1易得自β-酮酯,在温和的反应条件下与伯胺和仲胺进行取代反应,得到4-烷基氨基类似物2.1与取代的苯肼的反应得到相应的或吡唑啉酮,以及作为产物混合物的5-烷氧基-1 H-吡唑.
DOI:10.1016/j.Tet.2007.08.085

海关参考信息

2902600000-乙苯
2905121000-正丙醇
2909110000-乙醚
2912110000-甲醛
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-4412958-A
优先权日:1981-10-16
标题:Stereospecific synthesis of 5-phenyl-2S-pentanol
发明人：CUE JR BERKELEY W; MOORE BERNARD S
权利人:PFIZER
摘要:5-Phenyl-2S-pentanol is synthesized stereospecifically from S ethyl lactate. The method provides easily purified 5-phenyl-2S-pentanol useful in the synthesis of central nervous system active (CNS) agents such as levonantradol.

专利号:US-6846957-B2
优先权日:2002-11-22
标题 :Synthesis of 3-aminomethyl-1-propanol, a fluoxetine precursor
发明人：ZELENIN ALEXANDER
权利人:UNIV TEXAS
摘要:The present invention concerns a method of synthesizing fluoxetine hydrochloride. The method includes the synthesis of 3-methylamino-1-phenyl-1-propanol by reduction of 1-phenyl-3-methylamino-2-propen-1-one with sodium borohydride and acetic acid.

专利号:US-6838581-B2
优先权日:2002-12-04
标题:Process for the preparation of enantiomerically pure 3-phenyl-3-hydroxypropylamine
发明人：KUMAR PRADEEP; PANDEY RAJESH KUMAR
权利人:COUNCIL SCIENT IND RES
摘要:The present invention relates to an improved process for the synthesis of enantiomerically pure 3-phenyl-3-hydroxypropylamine of formula I; more particularly the present invention relates to the said process using styrene; n n nthe synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the target compound, using styrene, a readily accessible starting material gives the optically pure dihydroxy compound (ee >97%; the selective monotosylation of primary alcohol, nucleophilic displacement by cyano and subsequent reduction to amino group furnishes the desired 3-phenyl-3-hydroxypropylamine in enatiomerically pure form, a key intermediate in the synthesis of variety of oxetine related anti-depressant drugs.

专利号:WO-2017071871-A1
优先权日:2015-10-27
标题:Synthesis of ketone releasing photo-cages
发明人：GERKE THOMAS; KROPF CHRISTIAN; HUCHEL URSULA; GRIESBECK AXEL; LANDES AGNIESZKA
权利人:HENKEL AG & CO KGAA
摘要:The invention relates to the production of specific ketones of formulae (I) and (VI), as defined herein, which act as photolabile pro-fragrances.

专利号:US-12252473-B2
优先权日:2022-04-18
标题:Preparation methods of quinolone compounds and intermediates thereof
发明人：LEI JIE; CHEN ZHONGZHU; XU ZHIGANG; TANG DIANYONG; XU JIAYU; ZHOU HAOYI; XIA DANDAN; LIU YAO; CAO YIHUA; LUO JIE
权利人:UNIV CHONGQING ARTS & SCIENCES
摘要:The present application relates to processes for the preparation of quinolone compounds and intermediates thereof, particularly to processes for the preparation of quinolones and pharmaceutical intermediates of the quinolones. In particular, the present application provides a process for the preparation of a compound of Formula I, and a process for the synthesis of quinolone compounds using the compound of Formula I as an intermediate. The process for the preparation of the compound of Formula I comprises the steps of:reacting a compound of Formula A with R5NH2 and R6Cl in the presence of a base to form the compound of Formula I,

专利号:US-4921798-A
优先权日:1989-09-25
标题 :Synthesis of (aryl or arylalkyl)-3-hydroxy propionic acids and aryl alkanediols having high optical purity
发明人：BOAZ NEIL W
权利人:EASTMAN KODAK CO
摘要:R- and S-1-Phenyl-1,3-propanediol, each of high optical purity, were prepared by a chemoenzymatic sequence starting with ethyl benzoylacetate. The first step was a catalytic hydrogenation of the Î²-ketoester conducted at room temperature. The enzymatic hydrolysis of the resulting hydroxyester proceeded in a facile manner using a commercial preparation of the lipase from Pseudomonas fluorescens. The enzymatic hydrolysis proceeded at a moderate rate (350 mg lipase/0.10 mol of racemic ester required a 20-hour reaction time with an enantiomeric rate ratio (E value) of 36). The hydrolysis was run to 45-50% conversion to afford isolated S-3-phenyl-3-hydroxypropionic acid of 85-90% ee after separation from the residual ester (aqueous base extraction). The optical purity of the hydroxy acid was determined by conversion to the methyl ester (CH 3 I, KHCO 3 , acetone), and derivatization with S-MTPA-Cl, and 1 H NMR analysis. A single recrystallization of the isolated acid afforded optically pure (>98% ee) S-3-phenyl-3-hydroxypropionic acid in an overall 36% yield from the racemic ester. The acid was reduced with borane in THF to afford optically purs S-diol in 97% yield after crystallization. The overall sequence proceeded in 34% total yield from racemic ester with an additional 45-55% recovered as the antipodal ester. This antipodal ester is obtained in 85-95% ee, and the corresponding hydroxy-acid was readily obtained (NaOH), CH 3 OH/H 2 O) and recrystallized to optical purity. Reduction then afforded R-1-phenyl-1,3-propanediol in 30% to overall yield from racemic ester.

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主要参考文献

[参考文献]: Keisuke Gondo, Et Al. Reaction Of Iodonium Ylides Of 1,3-Dicarbonyl Compounds With Hf Reagents. Molecules. 2012 May 31;17(6):6625-32.
[参考文献]: Kuang-Po Chen, Et Al. Free Radical Reaction Between 2-Benzoyl-1,4-Benzoquinones And 1,3-Dicarbonyl Compounds. Org Biomol Chem. 2009 Oct 7;7(19):4074-81.
[参考文献]: Tsugio Kitamura, Et Al. A Practical And Convenient Fluorination Of 1,3-Dicarbonyl Compounds Using Aqueous Hf In The Presence Of Iodosylbenzene. Org Lett. 2011 May 6;13(9):2392-4.
[参考文献]: Ugo Battaglia, Et Al. A Short Synthesis Of The Triazolopyrimidine Antibiotic Essramycin. J Nat Prod. 2010 Nov 29;73(11):1938-9.

合成参考文献

摘要:Nahm Garrett, M.; Johnson, J. S., Science of Synthesis Knowledge Updates, (2012) 2, 27.
摘要:Aguilar, E.; López, L. A., Science of Synthesis Knowledge Updates, (2014) 2, 11.
摘要:Hou, X.-L.; Peng, X.-S.; Yeung, K.-S.; Wong, H. N. C., Science of Synthesis Knowledge Updates, (2011) 2, 266.
摘要:Hou, X.-L.; Peng, X.-S.; Yeung, K.-S.; Wong, H. N. C., Science of Synthesis Knowledge Updates, (2011) 2, 271.
摘要:Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 51.

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CAS: 94-02-0; Ethyl 3-Oxo-3-Phenylpropanoate

该化合物是一种多用途有机化合物,具有多种好处,其化学稳定性和对水解的耐受性很高,因此适合于香水,香味和药品生产的各种应用,此外,其芳香特性有助于其作为溶剂和有机合成反应中间剂的用途.

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