CAS: 1132-26-9; 2-Amino-2-Methyl-3-Phenylpropanoic Acid

该化合物是一种非蛋白性α-氨酸,其成分为苯基组和一个四硝基碳中心.它的独特结构将一个甲基组和一个在α-碳的苯替代体结合在一起,使其成为有机合成和制药研究中宝贵的手艺建筑块.化合物的骨干受到极大阻碍,骨干能够增强稳定性,而其氨基和碳箱基功能组则允许多用途衍生.它特别适用于流行学和生物活性分子的中间体.这个僵硬框架有助于对设计成的片进行符合性控制,从而有利于研究结构-活性关系.高纯度等级可以确保研究应用中的再生性.

结构式图片

相似化合物

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合成工艺路线路线简述

  • 合成目标产物 2-Amino-2-Methyl-3-Phenylpropionic Acid 主要起始原料 Benzyl Chloride
  • (文献来源)合成步骤主要原料 Benzyl Chloride
📜氯化苄置于苄基三乙基氯化铵 盐酸,氢氧化钾,Potassium Carbonate体系中,用 二氯甲烷 用作溶剂,化学反应 22.0H,反应生成Alpha-甲基-Dl-苯丙氨酸
参考文献:苯甲醛亚胺的烷基化和亲核加成固相转移催化合成α-氨基酸
标题:苯甲醛亚胺的烷基化和亲核加成固相转移催化合成α-氨基酸
摘要:研究了在固-液相转移催化条件下,通过烷基化,迈克尔加成和羰基加成以及甘氨酸和丙氨酸酯衍生的亚胺与苯甲醛环加成,合成短而温和高效的α-氨基酸的路线.固液相转移催化反应的关键是为各种反应物选择碱.产量取决于所用的碱.讨论了使用koh,K 2 Co 3和na 2 Co 3获得的结果.研究了固液ptc苄基化反应的动力学,我们提出了一种可能的固液ptc机理作为界面自动催化程序.介绍了一些α-氨基酸合成的细节.
Doi:10.1016/s0040-4020(01)86041-5

海关参考信息

专利信息


专利号:US-7763734-B2
优先权日:2006-04-19
标题 :Synthesis, structure and use of bisoxazolidines for asymmetric catalysis and synthesis
发明人:WOLF CHRISTIAN; LIU SHUANGLONG
权利人:UNIV GEORGETOWN
摘要:One aspect of the invention relates to chiral bisoxazolidines and their use in asymmetric catalysis. The chiral bisoxazolidines are a novel class of compounds that is expected to find multiple applications, for example, in asymmetric synthesis. For example, a bisoxazolidine ligand enabled the catalytic enantioselective alkynylation and alkylation of a range of aromatic and aliphatic aldehydes, generating chiral propargylic alcohols and secondary alcohols in high yields and enantiomeric excess.

专利号:US-5892038-A
优先权日:1997-12-08
标 题 :Hydroxy-amino acid amides
发明人:DOLLE III ROLAND ELLWOOD; PATEL HITESH K
权利人:PHARMACOPEIA INC
摘要:Compounds of Formula I I are disclosed as inhibitors of plasmepsin and cathepsin D. The compounds are therefore useful to treat diseases such as malaria. In preferred compounds of formula I, Y is the residue of an N-acylated amino acid, a substituted 4-aminoproline or a substituted piperazinealkanoic acid. Intermediates in the solid phase synthesis of compounds of formula I, in which the compounds are attached to a solid support, are also disclosed.

专利号:US-7947722-B2
优先权日:2006-07-28
标 题:Imidazolidinone derivative, method of producing the same and method of producing optically active amino acid
发明人:SAKA YASUHIRO; FUJII AKIO; OKURO KAZUMI; MITSUDA MASARU
权利人:KANEKA CORP
摘要:The objective of the present invention is to provide an optically active imidazolidinone derivative widely usable for synthesizing an optically active amino acid, a method of easily producing the derivative, and a method of easily producing an optically active amino acid by using the derivative. The objective can be achieved by producing an optically active amino acid using a novel optically active imidazolidinone derivative represented by a general formula (3) and the like. According to the method of the present invention, an optically active imidazolidinone derivative can be obtained by preferential crystallization from a mixture of isomers of the imidazolidinone derivative. Therefore, an optically active amino acid can be easily and stereoselectively produced without cumbersome procedures required for the conventional methods, such as resolution of diastereomers, synthesis from an optically active amino acid and resolution of isomers by silica gel column chromatography.

专利号:US-2010190794-A1
优先权日:2007-06-12
标 题:Herbicidally Active Composition
发明人:HUPE EIKE; MOBERG WILLIAM KARL; REINHARD ROBERT; SIEVERNICH BERND; KIBLER ELMAR
权利人:BASF SE
摘要:The present invention relates to herbicidally active compositions comprising at least one piperazinedione compound of the formula I n n n n n n n n n n n n in which: n R x , R y are each hydrogen or together are a chemical bond; n R 1 is cyano or nitro; n R 2 is hydrogen, fluorine, chlorine, C 1 -C 2 -alkyl, ethenyl or C 1 -C 2 -alkoxy; n R 3 is fluorine or hydrogen; n R 4 is methyl; n R 5 is hydrogen, methyl or ethyl; n R 6 is hydrogen, methyl or ethyl; and n R 7 is hydrogen or halogen; n and at least one further active compound selected from the group consisting of n b1) lipid biosynthesis inhibitors; n b2) acetolactate synthase inhibitors (ALS inhibitors); n b3) photosynthesis inhibitors; n b4) protoporphyrinogen-IX oxidase inhibitors, n b5) bleacher herbicides; n b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); n b7) glutamine synthetase inhibitors; n b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); n b9) mitose inhibitors; n b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); n b11) cellulose biosynthesis inhibitors; n b12) decoupler herbicides; n b13) auxin herbicides; n b14) auxin transport inhibitors; n b15) other herbicides, and n C) safeners.

专利号:US-2010121022-A1
优先权日:2006-10-17
标 题 :1,3-dipolar cycloaddition of azides to alkynes
发明人:MUSA OSAMA M; SRIDHAR LAXMISHA M; YUAN-HUFFMAN QINGWEN WENDY
权利人:MUSA OSAMA M; SRIDHAR LAXMISHA M; YUAN-HUFFMAN QINGWEN WENDY
摘要:A process for the bulk polymerization, in the absence of any solvent, of a reactant containing azide functionality and a reactant containing a terminal alkyne functionality, in the presence of Cu (I) catalyst or in the presence of a Cu(II) catalyst without a reducing agent, is described. Polymerization can be achieved at temperatures less than 100° C., which is suitable for low temperature cures. A controlled synthesis for low molecular weight oligomers is disclosed.

专利号:US-5872262-A
优先权日:1996-11-05
标 题:Hydroxy-amino acid amides
发明人:DOLLE ROLAND ELLWOOD III; JOHNSON THEODORE O JR; TAO SHIWEI
权利人:PHARMACOPEIA INC
摘要:Compounds of Formula I I are disclosed as inhibitors of plasmepsin and cathepsin D. The compounds are therefore useful to treat diseases such as malaria. In preferred compounds of formula I, Y is the residue of an N-acylated amino acid, a substituted 4-aminoproline or a substituted piperazinealkanoic acid. Intermediates in the solid phase synthesis of compounds of formula I, in which the compounds are attached to a solid support, are also disclosed.

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主要参考文献

[参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-818.
[参考文献]: A T Wyse, Et Al. Alanine Prevents The Decrease Of Na+,K+-Atpase Activity In Experimental Phenylketonuria. Metab Brain Dis. 1999 Jun;14(2):95-101.
[参考文献]: A T Wyse, Et Al. Effect Of Phenylalanine And Its Metabolites On Atp Diphosphohydrolase Activity In Synaptosomes From Rat Cerebral Cortex. Neurochem Res. 1994 Sep;19(9):1175-80.
[参考文献]: Elisa Costabeber, Et Al. Hyperphenylalaninemia Reduces Creatine Kinase Activity In The Cerebral Cortex Of Rats. Int J Dev Neurosci. 2003 Apr;21(2):111-6.
[参考文献]: Griet Van Zeebroeck, Et Al. Transport And Signaling Via The Amino Acid Binding Site Of The Yeast Gap1 Amino Acid Transceptor. Nat Chem Biol. 2009 Jan;5(1):45-52.

合成参考文献


参考文献:10.1126/science.944951
摘要:Greengard O, Yoss MS, Del Valle JA. Alpha-methylphenylalanine, a new inducer of chronic hyperphenylalaninemia in sucling rats. Science. 1976 Jun 04;192(4243):1007–8. doi: 10.1126/science.944951.
参考文献:10.1007/bf00967744
摘要:Huether G. The depletion of tryptophan and serotonin in the brain of developing hyperphenylalaninemic rats is abolished by the additional administration of lysine. Neurochem Res. 1986 Dec;11(12):1663–8. doi: 10.1007/bf00967744.
参考文献:10.1038/nchembio.132
摘要:Van Zeebroeck G, Bonini BM, Versele M, Thevelein JM. Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor. Nat Chem Biol. 2009 Jan;5(1):45–52. doi: 10.1038/nchembio.132.
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