Cu-MOF/FeOOH复合材料在水相中催化合成四氢噻吩类衍生物
Cu-MOF/FeOOH Composites Catalyzed Synthesis of Tetrahydrophene Derivatives in Water
DOI: 10.12677/HJCET.2021.115035, PDF,    科研立项经费支持
作者: 惠永海, 张永飞, 余 彪, 韩 冰, 李建鹏*：岭南师范学院化学化工学院，海洋绿色精细化学品实验室，广东 湛江
关键词: Cu-MOF/FeOOH复合材料；2¸5-二羟基-1¸4-二噻烷；四氢噻吩；串联反应；Cu-MOF/FeOOH Composite； 2¸5-Dihydroxy-1¸4-Dithiane； Tetrahydrothiophenes； Tandem Reaction
摘要: 制备了Cu-MOF/FeOOH复合材料，并作为催化剂，在水相中对硝基烯和2,5-二羟基-1,4-二噻烷进行了串联环化反应的催化性能研究。以较高产率(最高达98%)合成了系列四氢噻吩类化合物，并对反应放大量实验和催化剂循环再利用进行了系统研究，最后探讨了可能的反应机理。该方法具有操作简单、反应时间短和环境友好等特点，为四氢噻吩环的构建提供了理论依据。
Abstract: Cu-MOF/FeOOH composite was prepared and used as catalyst to study the catalytic performance of series cyclization of nitroene and 2,5-dihydroxy-1,4-dithiane in aqueous phase. A series of Tetrahydrothiophene compounds were synthesized in high yield (up to 98%), and the reaction experiments and catalyst recycling were systematically studied. Finally, the possible reaction mechanism was discussed. The method has the characteristics of simple operation, reaction time and environmental friendliness, which provides a theoretical basis for the construction of tetrahydrothiophene ring.
文章引用：惠永海, 张永飞, 余彪, 韩冰, 李建鹏. Cu-MOF/FeOOH复合材料在水相中催化合成四氢噻吩类衍生物[J]. 化学工程与技术, 2021, 11(5): 260-266. https://doi.org/10.12677/HJCET.2021.115035

参考文献

[1] Amspacher, D.R., Blanchard, C.Z., Fronczek, F.R., Saraiva, M.C., Waldrop, G.L. and Strongin, R.M. (1999) Synthesis of a Reaction Intermediate Analogue of Biotin-Dependent Carboxylases via a Selective Derivatization of Biotin. Organic Letters, 1, 99-102. [Google Scholar] [CrossRef] [PubMed]
[2] Yoshikawa, M., Morikawa, T., Matsuda, H., Tanabe, G. and Muraoka, O. (2002) Absolute Stereostructure of Potent α-Glucosidase Inhibitor, Salacinol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure from Salacia Reticulata. Bioorganic & Medicinal Chemistry, 10, 1547-1554. [Google Scholar] [CrossRef] 
[3] Yoshikawa, M., Murakami, T., Yashiro, K. and Matsuda, H. (1998) Kotalanol, a Potent α-Glucosidase Inhibitor with Thiosugar Sulfonium Sulfate Structure, from Antidiabetic Ayurvedic Medicine Salacia Reticulata. Chemical & Pharmaceutical Bulletin, 46, 1339-1340. [Google Scholar] [CrossRef] [PubMed]
[4] Johnson, J.W., Evanoff, D.P., Savard, M.E., Lange, G., Ramadhar, T.R., Assoud, A., Taylor, N.J. and Dmitrienko, G.I. (2008) Cyclobutanone Mimics of Penicillins: Effects of Substitution on Conformation and Hemiketal Stability. The Journal of Organic Chemistry, 73, 6970-6982. [Google Scholar] [CrossRef] [PubMed]
[5] Volkmann, R.A., Kelbaugh, P.R., Nason, D.M. and Jasys, V.J. (1992) 2-Thioalkyl Penems: An Efficient Synthesis of Sulopenem, a 5R, 6S-6-(1(R-Hydroxyethyl)-2-[(cis-1-oxo-3-Thiolanyl)thiol-2-Penem Antibacterial. The Journal of Organic Chemistry, 57, 4352-4361. [Google Scholar] [CrossRef] 
[6] Yoshimura, Y., Watanabe, M., Satoh, H., Ashida, N., Ijichi, K., Sakata, S., Machida, H. and Matsuda, A. (1997) A Facile, Alternative Synthesis of 4’-Thioarabinonucleosides and Their Biological Activities. Journal of Medicinal Chemistry, 40, 2177-2183. [Google Scholar] [CrossRef] [PubMed]
[7] Brandau, S., Maerten, E. and Jørgensen, K.A. (2006) Asymmetric Syn-thesis of Highly Functionalized Tetrahydrothiophenes by Organocatalytic Domino Reaction. Journal of American Chemical Society, 128, 14986-14991. [Google Scholar] [CrossRef] [PubMed]
[8] Robertson, F.J. and Wu, J. (2012) Phosphorothioic Acids and Related Compounds as Surrogates for H2S Synthesis of Chiral Tetrahydrothiophenes. Journal of American Chemical Society, 134, 2775-2780. [Google Scholar] [CrossRef] [PubMed]
[9] Ling, J.B., Su, Y., Zhu, H.L., Wang, G.Y. and Xu, P.F. (2012) Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahy-drothiophenes. Organic Letters, 14, 1090-1093. [Google Scholar] [CrossRef] [PubMed]
[10] Su, Y., Ling, J.B., Zhang, S. and Xu, P.F. (2013) Organocatalytic Cascade Sulfa-Michael/Aldol Reaction of β,β-Disubstituted Enones: Enantioselective Synthesis of Tetrahydrothiophenes with a Trifluoromethylated Quaternary Center. The Journal of Organic Chemistry, 78, 11053-11058. [Google Scholar] [CrossRef] [PubMed]
[11] Baricordi, N., Benetti, S., Bertolasi, V. and Risi, C.D. (2012) 1,4-Dithiane-2,5-Diol as an Efficient Synthon for a Straightforward Synthesis of Functionalized Tetrahydrothiophenes via Sulfa-Michael/Aldol-Type Reactions with Electrophilic Alkenes. Tetrahedron, 68, 208-213. [Google Scholar] [CrossRef] 
[12] Song, J., Moss, J., Yang, D.C., Guan, Z. and He, Y.H. (2014) Catalyst-Free Synthesis of Trisubstituted Tetrahydrothiophenes in Water via a Cascade Sulfamichael/aldol (Henry) Type Reaction. RSC. Advances, 4, 54032-54038. [Google Scholar] [CrossRef] 
[13] Du, J.G., Tao, M.L. and Zhang, W.Q. (2016) Fiber-Supported Acid-Base Bifunctional Catalysts for Efficient Nucleophilic Addition in Water. ACS Sustainable Chemistry & Engineering, 4, 4296-4304. [Google Scholar] [CrossRef]