1. 毕业设计（论文）的内容和要求

2,3-二氢苯并〔b〕呋喃衍生物是医药和农药的重要中间体，是有机合成领域近期研究的热点之一。

本论文要求学生在查阅文献的基础上制定实验方案，并完成实验室工作，合成出合格产品，并完成毕业论文撰写，通过本科生毕业论文答辩。

2. 参考文献

[1] Choi M, Jo H, Park H, et al. Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB[J]. Bioorganic Medicinal Chemistry Letters. 2015, 25(12): 2545-2549. [2] Dawood K M, Fuchigami T. Electrochemical Partial Fluorination of Organic Compounds. 74. Efficient Anodic Synthesis of 2-Fluoro- and 2,3-Difluoro-2,3-dihydrobenzofuran Derivatives1[J]. The Journal of Organic Chemistry. 2004, 69(16): 5302-5306. [3] Shi G Q, Dropinski J F, Zhang Y, et al. Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids: Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity[J]. Journal of Medicinal Chemistry. 2005, 48(17): 5589-5599. [4] Patel M R, Bhatt A, Steffen J D, et al. Discovery and Structure#8211;Activity Relationship of Novel 2,3-Dihydrobenzofuran-7-carboxamide and 2,3-Dihydrobenzofuran-3(2H)-one-7-carboxamide Derivatives as Poly(ADP-ribose)polymerase-1 Inhibitors[J]. Journal of Medicinal Chemistry. 2014, 57(13): 5579-5601. [5] Pettersson M, Johnson D S, Subramanyam C, et al. Design and synthesis of dihydrobenzofuran amides as orally bioavailable, centrally active γ-secretase modulators[J]. Bioorganic Medicinal Chemistry Letters. 2012, 22(8): 2906-2911. [6] Ye X, Morales C L, Wang Y, et al. Synthesis and structure#8211;activity relationship of dihydrobenzofuran derivatives as novel human GPR119 agonists[J]. Bioorganic Medicinal Chemistry Letters. 2014, 24(11): 2539-2545. [7] Micic N, Polyzos A. Radical Carbonylation Mediated by Continuous-Flow Visible-Light Photocatalysis: Access to 2,3-Dihydrobenzofurans[J]. Organic Letters. 2018, 20(15): 4663-4666. [8] Kuethe J T, Wong A, Journet M, et al. A Rapid Synthesis of 2-Aryl-5-substituted-2,3-dihydrobenzofurans[J]. The Journal of Organic Chemistry. 2005, 70(9): 3727-3729. [9] Sakate S S, Shinde S H, Kasar G B, et al. Cascade synthesis of dihydrobenzofuran via Claisen rearrangement of allyl aryl ethers using FeCl 3 /MCM-41 catalyst[J]. Journal of Saudi Chemical Society. 2018, 22(4): 396-404. [10] Zhou Z, Liu G, Chen Y, et al. Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C#8211;H Functionalization/Cyclization[J]. Organic Letters. 2015, 17(23): 5874-5877. [11] Shaikh A K, Varvounis G. Novel Synthesis of 3-Substituted 2,3-Dihydrobenzofurans viaortho-Quinone Methide Intermediates Generatedin Situ[J]. Organic Letters. 2014, 16(5): 1478-1481. [12] Kato M, Saito A. Domino Synthesis of 2,3-Dialkylidenetetrahydrofurans via Tandem Prins Cyclization#8211;Skeletal Reorganization[J]. Organic Letters. 2018, 20(15): 4709-4712. [13] Mangas-Sa#769;nchez J, Busto E, Gotor-Ferna#769;ndez V, et al. Straightforward Synthesis of Enantiopure 2,3-Dihydrobenzofurans by a Sequential Stereoselective Biotransformation and Chemical Intramolecular Cyclization[J]. Organic Letters. 2010, 12(15): 3498-3501. [14] Sun Z, Zhou T, Pan X, et al. Design, synthesis and biological evaluation of a series of novel GPR40 agonists containing nitrogen heterocyclic rings[J]. Bioorganic Medicinal Chemistry Letters. 2018, 28(18): 3050-3056. [15] Murphy R A, Kung H F, Kung M P, et al. Synthesis and characterization of iodobenzamide analogues: potential D-2 dopamine receptor imaging agents[J]. J Med Chem. 1990, 33(1): 171-178. [16] Liu G, Xu B. Hydrogen bond donor solvents enabled metal and halogen-free Friedel#8211;Crafts acylations with virtually no waste stream[J]. Tetrahedron Letters. 2018, 59(10): 869-872. [17] Matsunaga N, Kaku T, Ojida A, et al. C17,20-lyase inhibitors. Part 2: Design, synthesis and structure#8211;activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors[J]. Bioorganic Medicinal Chemistry. 2004, 12(16): 4313-4336. [18] Smith K, El-Hiti G A, Jayne A J, et al. Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent-free system. Scope of the reaction for substituted ethers[J]. Organic biomolecular chemistry. 2003, 1(9): 1560-1564. [19] 欧阳杰. 2,3-二氢苯并〔b〕呋喃衍生物的合成[J]. 吉林化工学院学报. 1997(03): 38-41. [20] 蒲文臣，王飞，王淳. 2-芳基苯并呋喃衍生物的生物活性与合成策略[J]. 有机化学. 2011(02): 155-165. [21] 潘文燕. 2-乙内酰硫脲类和二氢苯并呋喃乙酸类手性药物衍生物及其中间体的色谱分离研究[D]. 山东大学, 2017. [22] 夏万东. 4-乙烯基-2,3-二氢苯并呋喃的合成[J]. 煤炭与化工. 2017(03): 81-82. [23] 王云侠，赵宇，王兰英，等. 5-甲氧基-2-苯基-2,3-二氢苯并呋喃的制备#8212;#8212;介绍一个大学综合化学实验[J]. 大学化学. 2018(01): 69-72. [24] 李莹超. 5-取代二氢苯并呋喃#8212;咪唑盐化合物的设计合成与生物活性研究[D]. 云南大学, 2015. [25] 郑静，方霞. 5-乙酰基-2,3-二氢苯并呋喃的合成[J]. 精细化工中间体. 2007(04): 34-35. [26] 艾春波，黎莲娘. 丹酚酸B的合成研究，2－苯基二氢苯并呋喃衍生物的合成[J]. Journal of Chinese Pharmaceutical Sciences. 1995(03): 161-164. [27] 黎哲. 可见光诱导酚类溴代及二氢苯并呋喃衍生物的合成研究[D]. 哈尔滨工业大学, 2013. [28] 王海飞，周志鹏，胡舜钦，等. 哌啶乙酸盐催化合成2,3-二取代-苯并二氢吡喃-4-酮和2,2-二取代-苯并呋喃-3-酮类衍生物[J]. 有机化学. 2016(03): 596-603. [29] 宋文建，羊晓东，王宇，等. 以Claisen重排产物为原料合成苯并呋喃衍生物研究进展[J]. 云南化工. 2009(01): 52-56. [30] 杉琦重治，蒲山真一，武藤英吾，稻坦敦土，冈田贵志. 光学活性的胺衍生物的制备方法200580038847.8[P]. 2007.10.17.

3. 毕业设计（论文）进程安排

2018.12 布置课题 2019.01.15前完成开题报告 2019.02.25-2019.03.10 完成实验方案的制定及实验前 期准备工作 2019.03.11-2019.05.30完成实验工作 2019.06.01-2019.06.10撰写论文，准备答辩。