CAS: 122-57-6; 4-Phenylbut-3-En-2-One

该化合物是一种在有机合成和工业应用中广泛使用的α,β-不饱和的氯酮.它的共生双壳系统使它成为Michael添加,高温凝聚和其他C-C联动反应的宝贵中间体.由于它的电益解β-碳,复合物具有有利的反应性,从而能够进行有效的核生殖性攻击.Benzylideneacetone也因其温和的气味而被用作调味剂和香味成分.它在室内温度下的晶状固体形式可以确保易于处理和储存.有了明确界定的熔点(41-43°C)和普通有机溶剂中的溶解性,它提供了实验室和制造过程中的多变性.由于潜在的皮肤和眼刺激,建议适当处理.

结构式图片

相似化合物

937-53-1 62413-47-2 113474-86-5

欧盟法规

REACH注册ECHA物质化妆品禁用物质清单C&L通报REACH预注册

上下游产品

methyl magnesium iodide cinnamonitrile diethyl ether (E)-3-phenylacrylic acid3-acetyl-4-phenyl-2-pyrazoline 1-(α-furyl)-5-phenylpenta-1,4-dien-3-one t-benzo[1,3]dioxol-5-yl-5t-phenyl-penta-1,4-dien-3-one1t-benzo[1,3]dioxol-5-yl-5t-phenyl-penta-1,4-dien-3-one 2-styrylquinoline-4-carboxylic acid

合成工艺路线路线简述

  • 合成目标产物 Benzalacetone 主要起始原料 1,3-Dithiane, 2-Methyl-2-(2-Phenylethenyl)-
  • (文献来源)合成步骤主要原料 1,3-Dithiane, 2-Methyl-2-(2-Phenylethenyl)-
1,3,5,7-Cyclooctatetraene置于fe(Co)3*phch=ch(Me)Cho体系中,用 甲苯 用作溶剂,化学反应生成苄叉丙酮
参考文献:五坐标铁的单烯烃和二烯烃交换动力学及机理(0)
标题:五坐标铁的单烯烃和二烯烃交换动力学及机理(0)
摘要:各种单烯烃与苯乙烯在[fe(co)4(phch Ch 2)]中的交换通过离解过程进行,涉及fe(co)4中间体.配体交换系统(ⅰ)(烯酮=亚苄基丙酮,肉桂醛,查耳酮,或dypnone;多烯= Cyclohexa-和环庚-1,3-二烯,环庚三烯,循环octatetraene,的[fe(co)3(η 4-Enone) ] +多烯⇌的[fe(co)3(η 4-多烯)] +烯酮(i)或1,4-二苯基丁-1,3-二烯)是逐步的,包括速率确定的π-键合的co部分的脱螯作用.缔合和解离途径都被发现.讨论了二烯结构和烯酮取代基的影响.
Doi:10.1039/dt9800000999

海关参考信息

专利信息


专利号:US-9388131-B2
优先权日:2011-04-27
标题:Automated synthesis of small molecules using chiral, non-racemic boronates
发明人:BURKE MARTIN D; LI JUNQI; GILLIS ERIC P
权利人:UNIV ILLINOIS
摘要:Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.

专利号:US-5484949-A
优先权日:1993-01-29
标题:Method for the synthesis of α β-unsaturated ketones
发明人:TSUKASHIMA KEIICHI; NAKAJIMA MASASHI; FUJIMARU MASAYOSHI; SUZUKI KENJI
权利人:NIPPON SODA CO
摘要:The present invention relates to a method for the synthesis of alpha , beta -unsaturated ketones which comprises, in the method for the synthesis of alpha , beta -unsaturated ketones represented by general formula reacting aldehydes represented by general formula R1CHO (where R1 is as defined above) with alkali metal salt of acetoacetic acid represented by general formula sence as a catalyst of 3-azabicyclo[3,2,2]nonane, a cyclic secondary amine represented by general formula (1) (1) a cyclic secondary amine represented by general formula (2) (2) (where, l is 1 or more and up to 6, a ring with N is a 6-membered, 7-membered or 8-membered ring, the two neighbors of N are methylene, R3 is a lower alkyl group, its substitution position is at a carbon atom other than two those adjacent to N, and is an alicyclic group or a phenol group), or a secondary amine represented by general formula (3) CH3NHCH2R4(3) in a mixuture solvent of water and water-insoluble organic solvent, while keeping the pH constant with mineral acid, and by adjusting an amount of water.

专利号:WO-2015120485-A1
优先权日:2014-02-10
标 题:Water, bubble collapse and syngas species in the synthesis of graphene and its derivatives
发明人:SHANKMAN RICHARD S
权利人:PEERLESS WORLDWIDE LLC
摘要:Hydrodynamic cavitation-inducing inertial, non-inertial, and combination reactors are employed in the hydrothermal synthesis of graphene and its derivatives, both in solution and vapor. Various hydrodynamic cavitation reactor embodiments are revealed. Water is used to both nucleate and 'self-heal' graphene sheet growth in solution and vapor. Various methods of combustion, hydrothermal and dehydration synthesis of graphene and its derivatives are revealed. Additionally, water and ice are used as a substrate, both alone and in combination with other substrates, to grow and recover useful graphene and its derivatives.

专利号:WO-03050105-A2
优先权日:2001-12-10
标题 :Catalytic asymmetric synthesis of optically active compounds
发明人:HALLAND NIS; JOERGENSEN KARL ANKER; HANSEN TORE
权利人:CHEMINOVA AS; HALLAND NIS; JOERGENSEN KARL ANKER; HANSEN TORE
摘要:A one step catalytic asymmetric process for the synthesis of an optically active compound of formula la or lb wherein R is selected from C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, C1-7 haloalkoxy, halogen and hydroxy; R3 is H or C1-4 alkyl; R4 is selected from H, C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, COOH, CO-C1-7 alkoxy and an optionally substituted aryl or heterocycle; AR represents C1-7 alkyl, optionally substituted aryl, an optionally substituted heterocycle or AR and R4 may be bridged together forming part of a ring system; X is O or S; m is a number between 0-4; comprising the step of reacting a compound of the formula 2 with a compound of formula 3 in the presence of a catalytic amount of a chiral nitrogen containing organic compound.

专利号:US-7964743-B2
优先权日:2005-02-17
标 题:Catalyst for asymmetric synthesis, ligand for use therein, and process for producing optically active compound through asymmetric synthesis reaction using them
发明人:MIYAURA NORIO; YAMAMOTO YASUNORI
权利人:JAPAN SCIENCE & TECH AGENCY
摘要:Compounds represented by the following general formula (1a) or (1b). n nA complex comprising a center metal of rhodium and a compound represented by the following general formula (1a) or (1b) as a ligand. A catalyst for optically active beta-substituted carbonyl compound synthesis and catalyst for asymmetric 1, 2 addition reaction being composed of the complex. A method of production of an optically active beta-aryl compound from an alpha, beta-unsaturated compound and an aryl-boronic acid derivative and method of production of an optically active aryl alcohol compound from an aldehyde compound and aryl boronic acid derivatives using the catalyst. A complex comprising a center metal of palladium and a compound represented by the following general formula (1a) or (1b) as a ligand. A catalyst for asymmetric allylic substitution reaction being composed of the complex. A method of production of an optically active dialkyl (1,3-disubstituted propeny)malonate compound from a 1,3-disubstituted ally acetate compound and a dialkyl malonate and method of production of an optically active allylamine compound from a 1,3-disubstituted ally acetate compound and an amine compound. The compounds have not only the versatility of being usable in the synthesis of wide-ranging optically active aryl compounds but also the selectivity and reactivity permitting synthesis with high yield within a short period of time under industrially advantageous mild conditions.

专利号:US-6799120-B2
优先权日:2000-02-03
标 题:Nonredundant split/pool synthesis of combinatorial libraries
发明人:SEPETOV NIKOLAI F; ISSAKOVA OLGA L; BAUM STEPHEN A; OSTREM JAMES A
权利人:NANOSCALE COMBINATORIAL SYNTHE
摘要:The present invention includes methods for generating combinatorial libraries on solid phase supports in which increased productivity is achieved by pooling all common steps in synthesis without using a tracking or coding system to record the synthetic history of each compound. Methods for generating combinatorial libraries in which containers with random mixtures of solid phase particles are divided and combined together in non-random ways without the exchange of particles between containers are also provided. Various products are optionally produced in multi-stage syntheses according to the invention, such as oligomers and synthetic non-repetitive organic molecules. The methods additionally relate to the identification of each library component without adding extra synthetic, physical, optical, or electronic encoding steps during library synthesis. Combinatorial synthetic systems are also provided.
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主要参考文献

[参考文献]: Bin Cao, Et Al. Synthesis Of The Pyridinyl Analogues Of Dibenzylideneacetone (Pyr-Dba) Via An Improved Claisen-Schmidt Condensation, Displaying Diverse Biological Activities As Curcumin Analogues. Org Biomol Chem. 2012 Feb 14;10(6):1239-45.
[参考文献]: C Preston Pugh, Et Al. Multiple Udp-Glucuronosyltransferases In Human Liver Microsomes Glucuronidate Both R- And S-7-Hydroxywarfarin Into Two Metabolites. Arch Biochem Biophys. 2014 Dec 15:564:244-53.
[参考文献]: G Feron, Et Al. Microbial Production Of 4-Hydroxybenzylidene Acetone, The Direct Precursor Of Raspberry Ketone. Lett Appl Microbiol. 2007 Jul;45(1):29-35.
[参考文献]: Indrani Mitra, Et Al. Quantitative Structure-Activity Relationship Modeling Of Antioxidant Activities Of Hydroxybenzalacetones Using Quantum Chemical, Physicochemical And Spatial Descriptors. Chem Biol Drug Des. 2009 May;73(5):526-36.
[参考文献]: Jia Zhang, Et Al. Gas Phase Retro-Michael Reaction Resulting From Dissociative Protonation: Fragmentation Of Protonated Warfarin In Mass Spectrometry. J Mass Spectrom. 2012 Aug;47(8):1059-64.

合成参考文献


摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2009) 46, 80.
摘要:Abou-Hadeed, K.; Hansen, H.-J., Science of Synthesis, (2010) 45, 1090.
摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2009) 46, 73.
摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2009) 46, 63.
摘要:Takeda, T.; Tsubouchi, A., Science of Synthesis, (2009) 46, 77.
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