从硝基烯烃合成1-位取代的牛磺酸
摘要
牛磺酸是一种人体必需的含硫氨基酸,具有多种生理功能,已被广泛应用于临床和食品添加剂中；一些取代牛磺酸也具有重要的生理活性,因此取代牛磺酸的合成具有重要的意义。目前已有多种取代牛磺酸的合成方法,但是合成1-取代牛磺酸和1,1-二取代牛磺酸的方法并不十分理想,且对脂肪和芳香取代的牛磺酸的合成没有通用性。
本文开发了一种新的1-位取代牛磺酸的合成方法。首先从醛酮或烯烃出发,采用几种简单易行的方法制备了一系列硝基烯烃；然后通过硝基烯烃与黄原酸钠的亲核加成反应,以较好的产率合成了一系列硝基黄原酸酯；接着用过氧甲酸对硝基黄原酸酯氧化得到硝基磺酸,随后无需提纯直接经钯碳催化的氢气的还原,以中等的产率合成了一系列1-取代牛磺酸和几种1,1-二取代牛磺酸；并提出了过酸氧化硝基黄原酸酯的机理。
本文提出的这种1-位取代牛磺酸的合成方法适用于脂肪和芳香取代基的1-取代和1,1-二取代牛磺酸的制备。该方法具有原料易得,合成路线短,总体产率高,无盐法制备等优点,是一种比较通用的合成1-位取代牛磺酸的方法。
Taurine is an essential sulfur-containing amino acid due to its various physiological functions.It has been widely used in clinical and food additives. Some substituted taurines also show importantly physiological activity. Thus, it is desired to develop the efficient and practical synthetic methods for substituted taurines.Although several methods have been documented for the synthesis of 1-mono-and 1,1-disubstituted taurines, all of them are not versatile for aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines.
A versatile and practical synthesis of 1-mono-and 1,1-disubstituted taurines has been developed in this dissertation.A series of nitroolefins were prepared from aldehydes,ketones,or olefins by some convenient methods.They underwent the nucleophilic addition reaction with sodium ethylxanthan to give rise to nitroalkyl xanthates in satisfactory to good yields.After the oxidation with performic acid and subsequent reduction with hydrogen in the presence of Pd/C, the nitroalkyl xanthates were converted to 1-mono and 1,1-disubstituted taurines in moderate overall yields.
The current method can be used to synthesize both aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines. The method is indeed a versatile and practical route to the synthesis of 1-mono-and 1,1-disubstitued taurines because of readily available starting materials, good overall yields, short synthetic steps, and salt-free process.
本文开发了一种新的1-位取代牛磺酸的合成方法。首先从醛酮或烯烃出发,采用几种简单易行的方法制备了一系列硝基烯烃；然后通过硝基烯烃与黄原酸钠的亲核加成反应,以较好的产率合成了一系列硝基黄原酸酯；接着用过氧甲酸对硝基黄原酸酯氧化得到硝基磺酸,随后无需提纯直接经钯碳催化的氢气的还原,以中等的产率合成了一系列1-取代牛磺酸和几种1,1-二取代牛磺酸；并提出了过酸氧化硝基黄原酸酯的机理。
本文提出的这种1-位取代牛磺酸的合成方法适用于脂肪和芳香取代基的1-取代和1,1-二取代牛磺酸的制备。该方法具有原料易得,合成路线短,总体产率高,无盐法制备等优点,是一种比较通用的合成1-位取代牛磺酸的方法。
Taurine is an essential sulfur-containing amino acid due to its various physiological functions.It has been widely used in clinical and food additives. Some substituted taurines also show importantly physiological activity. Thus, it is desired to develop the efficient and practical synthetic methods for substituted taurines.Although several methods have been documented for the synthesis of 1-mono-and 1,1-disubstituted taurines, all of them are not versatile for aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines.
A versatile and practical synthesis of 1-mono-and 1,1-disubstituted taurines has been developed in this dissertation.A series of nitroolefins were prepared from aldehydes,ketones,or olefins by some convenient methods.They underwent the nucleophilic addition reaction with sodium ethylxanthan to give rise to nitroalkyl xanthates in satisfactory to good yields.After the oxidation with performic acid and subsequent reduction with hydrogen in the presence of Pd/C, the nitroalkyl xanthates were converted to 1-mono and 1,1-disubstituted taurines in moderate overall yields.
The current method can be used to synthesize both aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines. The method is indeed a versatile and practical route to the synthesis of 1-mono-and 1,1-disubstitued taurines because of readily available starting materials, good overall yields, short synthetic steps, and salt-free process.
引文
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[34]Yu H, Cao S L, Zhang L L, et al. Synthesis of α-Aliphatic and β-Aromatic Substituted Taurines via the Regioselective Ammonia Ring-Opening of Thiiranes[J]. Synthesis,2009, (13):2205-2209.
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[2]Raiha N, Rassin D, Heinonen K, et al. Milk protein quality and quantity:Biochemical and growth effects in low birth weight infants (LBWI)[J]. Pediatr Res.,1975,9:370.
[3]Hayes K C. A review on the biological function of taurine[J]. Nutrition rev.,1976,34(6): 161-165.
[4]Liebowitz S M, Lombardini J B, Salva P S. Effects of aminocycloalkanesulfonic acid analogs of taurine on ATP-dependent calcium ion uptake and protein phosphoryl-ation[J]. Biochem. Pharmac.,1988,37:1303.
[5]Della Corte L, Crichton R R, Duburs G, et al. The use of taurine analogues to investigate taurine functions and their potential therapeutic applications[J]. Amino Acids.,2002, 23(4):367-379.
[6]Xu J X. Synthesis of Hydroxyalkanesulfonic Acids, Aminoalkanesulfonic Acids and Sulfonopeptides[J]. Chin. J. Org. Chem.,2003,23(1):1-9.
[7]Timothy C, Birdsall N D. Therapeutic applications of taurine[J]. Alt. Med. Rev.,1998, 3(2):128-136.
[8]郝文利.牛磺胆酸的解热镇痛作用及其作用机理的研究[D].呼和浩特：内蒙石农业大学.
[9]Higashiura K, Ienaga K. Simple performic acid oxidation of acetylthio group to sulfonic acid and its application in syntheses of 2-substituted taurines[J]. J. Org. Chem.,1992, 57(2):764-766.
[10]Ricci L, Frosini M, Gaggelli N, et al. Valoti M. Inhibition of rabbit brain 4-aminobutyrate transaminase by some taurine analogues:A kinetic analysis[J].Biochem.Pharmacol.,2006, 71(10):1510-1519.
[11]Braghiroli D, Truzzi C, Brandoli C, et al. Effect of 2-methyltaurine and its enantiomers on arterial blood pressure[J]. Pharmacol. Res.,1996,34(1-2):33-36.
[12]Gold M H, Skebelsky M, Lang G. The Chemistry of Aliphatic Nitrosulfonates. Ⅱ. β-Amino Sulfonic Acids[J]. J. Org. Chem.,1951,16:1500-1502.
[13]Cordero F M. Cacciarini M, Machetti F, et al. Amino-sulfonation of alkenes in a three-component reaction[J]. Eur. J. Org. Chem.,2002:1407-1411.
[14]Grunder E, Leelerc G. Synthesis of (±)-erythro-and (±)-threo-1,2-diphenyltaurines by diastereoselective hydrolysis of thiazetidine 1,1-dioxides[J]. Synthesis,1989:135-137.
[15]Higashiura K, Morina H, Matsuura H, et al. Synthesis and properties of optically active 2-substituted taurines[J]. J. Chem. Soc. Perkin Trans.1,1989:1479-1481.
[16]Higashiura K, Toyomaki Y, Tenaga K. The chemical conversion of C-terminal glycines in peptides into taurine[J]. J. Chem. Soc., Chem. Commun,1989, (9):521-512.
[17]Braghiroli D, Di-Bella M. Asymmetric Synthesis of (R)-and (S)-2-Aminobutanesulfonic Acid and their 3,3-Dimethylderivatives[J]. Tetrahedron:Asymmetry,1996,7(7): 2145-2150.
[18]Braghiroli D, Di-Bella M. New methods for the preparation of 2-amino-2-methylpropane sulfonic acid[J]. Tetrahedron Lett.,1996,37(40):7319-7322.
[19]Zhang W, Wang B Y, Chen N, et al. Expeditious and practical synthesis of various
substituted taurines from amino alcohols[J].Synthesis,2008,2:197-200.
[20]Higashiura K, Ienaga K. Simple performic acid oxidation of acetythio grooup to sulfonic acid and its application in synthesis of 2-substituted taurines[J]. J. Org. Chem.1992,57: 764.
[21]Mitsunobu O, Yamada M. Preparation of esters of carboxylic and phosphoric acid via quaternary phosphonium salts[J]. Bull. Chem. Soc. Jpn.,1967,40(10):2380-2382.
[22]Moree W J, van-der-Marel G A, Liskamp R M J. Synthesis of peptidosulfinamides and peptidosulfonamides:peptidomimetics containing the sulfinamide or sulfonamide transition-state isostere[J].J. Org. Chem.,1995,60:5157-5169.
[23]Lowik-Dennis W P M, Liskamp-Rob M J. Synthesis of α-and β-substituted aminoethane sulfonamide arginine-glycine mimics[J].Eur. J. Org. Chem.,2000, (7):1219-1228.
[24]Xu J X, Xu S. Synthesis of N-protected 1-substituted and 1,2-disubstituted taurines[J]. Synthesis,2004,2:276-282.
[25]Xu J X, Xu S, Zhang Q H. The first synthesis of optically active 1-substituted taurines[J]. Hetero. Chem.,2005,6:466-471.
[26]Strecker A. Ueber die kunstliche bildung der milchsaure und einen neuen, dem glycocoll homologen korper[J]. Justus Liebigs Ann. Chem.,1850,75(1):27-45.
[27]Chen N, Jia W Y, Xu J X. A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines[J].Eur. J. Org. Chem.,2009:5841-5846.
[28]Xu J X. A new and expeditious asymmetric synthesis of (R)-and (S)-2-aminoalkane-sulfonic acids from chiral amino alcohols[J].Tetrahedron:Asymmetry,2002,13: 1129-1134.
[29]Chen N, Zhu M,Zhang W, et al. Synthesis of gem-disubstituted taurines by thregioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite[J].Amino Acid,2009,37(2),309-313.
[30]Hu L B, Zhu H, Du D M, et al. Efficient Synthesis of taurine and structurally diverse substituted taurines from aziridines[J]. J. Org. Chem.,2007,72:4543-4546.
[31]Huang J X, Wang F, Du D M, et al. An Expeditious synthesis of 1-substituted and cyclic yaurines[J]. Synthesis,2005:2122-2128.
[32]Huang J X, Du D M, Xu J X. Facile synthesis of 1,1-disubstituted taurines[J]. Synthesis, 2006:315-319.
[33]Bentley T W, Jones R V H, Larder A H, et al. Solvents as phase transfer catalyst. Reaction of trimethylsulfonium iodide and solid potassium hydroxide in acetonitrile leading to a epoxide of benzophenone[J]. J. Chem. Soc., Perkin Trans.2 1998, (6):1407-1411.
[34]Yu H, Cao S L, Zhang L L, et al. Synthesis of α-Aliphatic and β-Aromatic Substituted Taurines via the Regioselective Ammonia Ring-Opening of Thiiranes[J]. Synthesis,2009, (13):2205-2209.
[35]喻昊.1-取代牛磺酸的原子经济合成方法[D].北京：首都师范大学,2009.
[36]Negrimovsky V M,Derkacheva V M, Luk'Yanets E A, et al. Synthesis of sulfonated 1,2-dicyanobenzenes[J]. Phosphorus, Sulfur Silicon Relat. Elem.,1995,104(1-4):161-7.
[37]Ouvry G, Quiclet-Sire B, Zard S Z. β-Nitro xanthates as olefin precursors [J]. Org. Lett., 2003,5(16):2907-2909.
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