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An efficient and general approach for the synthesis of amphiphilic 1,2-amino alcohols is reported. The use of N-benzyl protecting groups is essential for obtaining good yields when opening a long-chain terminal epoxide with an amine. 相似文献
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Polina A. Petrova Denis V. Sudarikov Larisa L. Frolova Roman V. Rumyantcev Svetlana A. Rubtsova Aleksandr V. Kutchin 《Molecules (Basel, Switzerland)》2022,27(20)
For the first time, monoterpene trifluoromethylated β-hydroxy-benzyl-O-oximes were synthesized in 81–95% yields by nucleophilic addition of the Ruppert–Prakash reagent (TMSCF3) to the corresponding β-keto-benzyl-O-oximes based on (+)-nopinone, (−)-verbanone and (+)-camphoroquinone. Trifluoromethylation has been determined to entirely proceed chemo- and stereoselective at the C=O rather than C=N bond. Trifluoromethylated benzyl-O-oximes were reduced to the corresponding α-trifluoromethyl-β-amino alcohols in 82–88% yields. The structure and configuration of the compounds obtained have been established. 相似文献
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Fabian Kallmeier Dr. Beata Dudziec Dr. Torsten Irrgang Prof. Dr. Rhett Kempe 《Angewandte Chemie (International ed. in English)》2017,56(25):7261-7265
The development of reactions that convert alcohols into important chemical compounds saves our fossil carbon resources as alcohols can be obtained from indigestible biomass such as lignocellulose. The conservation of our rare noble metals is of similar importance, and their replacement by abundantly available transition metals, such as Mn, Fe, or Co (base or nonprecious metals), in key technologies such as catalysis is a promising option. Herein, we report on the first base-metal-catalyzed synthesis of pyrroles from alcohols and amino alcohols. The most efficient catalysts are Mn complexes stabilized by PN5P ligands whereas related Fe and Co complexes are inactive. The reaction proceeds under mild conditions at catalyst loadings as low as 0.5 mol %, and has a broad scope and attractive functional-group tolerance. These findings may inspire others to use Mn catalysts to replace Ir or Ru complexes in challenging dehydrogenation reactions. 相似文献
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The solid-phase syntheses of enkephalin and somatostatin analogues with C-terminal OH functions instead of the normal carboxylates are described. The OH function of the N-terminal amino alcohol was acylated with succinic acid and esterified to the solid support. Normal Boc-TFA solid-phase strategy can be applied to build up and cleave these peptides. The succinic ‘handle’ can be removed by mild basic hydrolysis after cleavage. 相似文献
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Nina I. Simirskaya Nikolai V. Ignat’ev Michael Schulte Sergei G. Zlotin 《Mendeleev Communications》2012,22(6):317-319
Terminal alkynols react with formaldehyde and secondary amines in aqueous ionic liquid [emim]HSO–4 in the presence of Cu(OAc) to afford the corresponding 1-(a-hydroxyalkyl)- or 1-(b-hydroxyalkyl)-2-(aminomethyl)acetylenes in better yields in comparison with the reaction in conventional organic solvents. The catalytic system can be easily recovered and recycled. 相似文献
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Jan Eric Neuburger Alina Gazizova Sven Tiedemann Prof. Dr. Jan von Langermann 《European journal of organic chemistry》2023,26(34):e202201471
This study highlights the straight-forward synthesis of substituted 1,2-amino alcohols from simple and readily available aromatic methyl ketones. Starting from acetophenone derivatives, the straight-forward synthesis strategy involved an initial bromination of the alpha-positioned methyl group in the first step, followed by a simple hydrolysis to the hydroxyketone (2-hydroxyacetophenone). The hydroxylated intermediate was subsequently converted from Silicibacter pomeroyi to the final 1,2-amino alcohol by using the transaminase. The transaminase-catalyzed reaction proceeded with yields up to 62 % and always excellent enantiomeric excess of >99 %. Interestingly, the keto-enol-tautomerism of the hydroxyl ketone yields an unexpected amino alcohol isomer. 相似文献
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Sadigov O. A. Alimardanov H. M. Ismailova Sh. I. Babayev N. R. 《Russian Journal of Organic Chemistry》2020,56(6):1001-1005
Russian Journal of Organic Chemistry - 2-Aminocyclododecan-1-ol and 6(3)-aminodecahydro-1,4-ethanonaphthalen-5(2)-ols (mixture of isomers) were synthesized in two steps via oxidative... 相似文献
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在(S)-氨基丙醇及(R)-氨基丙醇手性臂的作用下, (M/P)-4,4'-二甲氧基-5,6,5',6'-二次甲二氧基-2-甲酸酯-2'-甲酰氨联苯经构型转化, 制备了光学纯轴手性联苯化合物(P, S)-3a 和(M, R)-3a. 测定了(P, S)-3a 的晶体结构及CD 光谱. 结果表明, 化合物(P, S)-3a 晶体属单斜晶系, P2(1)空间群, 晶胞参数为a=12.122(2) Å, b=8.9911(18) Å, c=12.779(3) Å, β=112.38(3)°, 在晶体中存在两组分子间氢键相互作用, 一组氢键由羟基氢与另一分子酰胺基团的羰基氧组成O-H…O,另一组由酰胺基团的NH 与另一分子酰胺基团的羰基氧构成N-H…O, 每一分子通过四个氢键与另外两个分子相连,构成棒状结构. 由CD 光谱确定了(M, R)-3b 的立体构型. 此外, 由(P, S)-3a 合成了轴手性化合物(P)-2,2'-二羟甲基-4,4'-二甲氧基-5,6,5',6'-二亚甲二氧基-联苯(6a). 相似文献
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QIAN Hui-Fena② HUANG Weib② LI Hui-Huib YAO Chenga a 《结构化学》2006,25(10):1243-1249
1 INTRODUCTION Chiral amino acids and their versatile derivatives are very useful compounds in many fields[1]. In com- parison with well-documented chiral α and β amino acids and amino alcohols, the studies of chiral γ, δ… ω amino acids and amino alcohols deserve more attention. For example, there have been numerous reports on versatile functions of γ aminobutyric acid (GABA) produced from L-glutamic acid in the presence of L-glutamate decarboxylase (GAD)[2]. However, the stereo… 相似文献
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Kathleen M. Morrison Dr. Charles S. Yeung Prof. Dr. Mark Stradiotto 《Angewandte Chemie (International ed. in English)》2023,62(23):e202300686
A systematic evaluation of competitive bisphosphine/Ni-catalyzed C−N versus C−O cross-couplings involving model compounds enabled development of hitherto unknown chemoselective O- and N-arylation of amino alcohols with (hetero)aryl chloride electrophiles, without recourse to protection group chemistry. Use of the CyPAd-DalPhos pre-catalyst C2 enabled particularly challenging O-arylation chemoselectivity in amino alcohols featuring branched primary and secondary alkylamine groups, while selective N-arylation was observed in substrates featuring less-hindered linear alkylamine and aniline reacting groups. Useful reaction scope in the (hetero)aryl chloride was achieved throughout, and the ability to conduct such transformations using benchtop handling of materials is demonstrated. 相似文献
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N. N. Makhmudiyarova K. I. Prokof’ev L. V. Mudarisova A. G. Ibragimov U. M. Dzhemilev 《Russian Journal of Organic Chemistry》2013,49(5):658-662
Efficient procedure was developed for 3-hetaryl-1,5,3-dithiazepanes and 3-hetaryl-1,5,3-dithiazocanes preparation from hetarylamines, N,N,N′,N′-tetramethylmethanediamine, and α,ω-alkanedithiols (ethane-1,2-dithiol, propane-1,3-dithiol), and also by the reaction of the latter with N,N-bis(methoxymethyl)hetarylamines in the presence of catalytic quantities of transition metals salts. 相似文献
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Murzakova N. N. Prokof’ev K. I. Tyumkina T. V. Ibragimov A. G. 《Russian Journal of Organic Chemistry》2012,48(4):588-593
Efficient procedures were developed for the synthesis of N-aryl-1,5,3-dithiazepanes and N-aryl-1,5,3-dithiazocanes by cyclocondensation of anilines with formaldehyde and α,ω-dithiols (etane-1,2-dithiol and propane-1,3-dithiol),
as well as by transamination of N-tert-butyl-1,5,3-dithiazepane or N-tert-butyl-1,5,3-dithiazocane with aromatic amines in the presence of samarium and cobalt complexes. 相似文献
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Rakhimova E. B. Ozden I. V. Meshcheryakova E. S. Khalilov L. M. Ibragimov A. G. 《Russian Journal of Organic Chemistry》2015,51(12):1788-1792
Russian Journal of Organic Chemistry - A procedure has been developed for the synthesis of N,N′-disubstituted bis-1,5,3-dithiazepanes by samarium-catalyzed recyclization of... 相似文献
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在替考拉宁手性柱上对阿替洛尔、美托洛尔、富马酸比索洛尔、普萘洛尔、异丙肾上腺素、沙丁胺醇及拉贝洛尔7种氨基醇类药物进行了对映体分离的研究.考察了流动相甲醇中添加少量酸碱以及酸碱不同比例对7种溶质的对映体分离的影响.固定极性有机相甲醇中冰醋酸和三乙胺的比例为1:1时,手性溶质的保留因子均随着流动相中冰醋酸/三乙胺含量的增加而减小,分离因子(α)基本保持不变,分离度减小.这可能是因为过量的酸增加了流动相的极性,使溶质较快被洗脱.在不加冰醋酸的情况下,除拉贝洛尔外,随着三乙胺浓度的增加,容量因子均减少,分离因子基本不变,分离度减小.这可能是因为三乙胺的增加使流动相的极性增加,溶质与手性固定相间的氢键减弱.结果表明:冰醋酸和三乙胺的比例并不影响手性分离的实质. 相似文献