2-(1-苯基亚乙基)丙二腈主要用于医药和农药领域,其合成方法包括无溶剂条件下醛与活性亚甲基化合物反应及甲苯-乙酸铵体系回流反应,产物结构经NMR确认。
医药; 农药
合成路线 1(1. 合成:5447-87-0)
产率:92%
合成条件:With 1,2-ethanediammonium 3-hydroxypropane-1-sulfonate In neat (no solvent) at 60℃; for 3 h; Green chemistry
实验步骤:通用程序:将[(EDA)(HPS)](10mol,0.0340g)在无溶剂条件下于60℃在搅拌的醛(1mmol)和活性亚甲基化合物(1.2mmol)的混合物中加入。 将反应混合物搅拌适当的时间(表2)。 通过TLC监测反应进程。 反应完成后,将温热的乙醇(5mL)加入到反应混合物中。 过滤有机催化剂并用温乙醇(2×10mL)完全洗涤,然后在室温下干燥。 减压蒸发剩余溶液中的溶剂,得到粗产物。 通过在含水乙醇中重结晶获得纯产物。
参考文献:
- [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 3, p. 428 - 431 [2] European Journal of Organic Chemistry, 2008, # 28, p. 4763 - 4768 [3] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4927 - 4928 [4] Synthetic Communications, 2000, vol. 30, # 5, p. 869 - 875 [5] Arkivoc, 2011, vol. 2011, # 9, p. 51 - 67 [6] Research on Chemical Intermediates, 2017, vol. 43, # 11, p. 6421 - 6432 [7] Synthetic Communications, 2004, vol. 34, # 17, p. 3219 - 3225 [8] Tetrahedron Letters, 2011, vol. 52, # 51, p. 6935 - 6938 [9] Synlett, 2016, vol. 27, # 9, p. 1433 - 1437 [10] RSC Advances, 2014, vol. 4, # 15, p. 7461 - 7470 [11] Tetrahedron, 2006, vol. 62, # 49, p. 11311 - 11319 [12] Catalysis Letters, 2017, vol. 147, # 1, p. 167 - 180 [13] Chinese Journal of Chemistry, 2013, vol. 31, # 10, p. 1348 - 1351 [14] Tetrahedron Letters, 2013, vol. 54, # 13, p. 1664 - 1668 [15] Patent: CN107151240, 2017, A. Location in patent: Paragraph 0184; 0185; 0186 [16] Organic Letters, 2013, vol. 15, # 20, p. 5298 - 5301 [17] Journal of Chemical Research, Synopses, 2001, # 1, p. 36 - 38 [18] Synthesis, 1994, # 3, p. 258 - 260 [19] Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3584 - 3591 [20] Tetrahedron, 2005, vol. 61, # 33, p. 7981 - 7985 [21] Patent: WO2017/118762, 2017, A1. Location in patent: Page/Page column 34; 35 [22] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 105 - 107 [23] Green Chemistry, 2009, vol. 11, # 6, p. 863 - 867 [24] Tetrahedron Letters, 1992, vol. 33, # 49, p. 7535 - 7538 [25] RSC Advances, 2015, vol. 5, # 99, p. 81415 - 81428 [26] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999, vol. 54, # 4, p. 541 - 543 [27] Chemistry Letters, 2000, # 9, p. 998 - 999 [28] Journal of Chemical Research, 2006, # 9, p. 561 - 562 [29] Tetrahedron Letters, 1996, vol. 37, # 7, p. 1113 - 1116 [30] Chemical Communications, 2015, vol. 51, # 29, p. 6411 - 6414 [31] Journal of the American Chemical Society, 1943, vol. 65, p. 991 [32] Journal of the American Chemical Society, 1945, vol. 67, p. 1050 [33] Journal of Organic Chemistry, 1966, vol. 31, p. 2784 - 2789 [34] Journal of the Chemical Society, 1961, p. 4705 - 4711 [35] Journal of Chemical Research, Miniprint, 1990, # 10, p. 2434 - 2452 [36] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 9, p. 834 - 836 [37] Journal of the American Chemical Society, 2003, vol. 125, # 38, p. 11460 - 11461 [38] Synthesis, 2005, # 4, p. 543 - 546 [39] Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 8, p. 1815 - 1827 [40] Tetrahedron Letters, 2009, vol. 50, # 34, p. 4833 - 4837 [41] Green Chemistry, 2009, vol. 11, # 4, p. 526 - 530 [42] Synthetic Communications, 2011, vol. 41, # 10, p. 1410 - 1420 [43] Organic and Biomolecular Chemistry, 2011, vol. 9, # 19, p. 6498 - 6501 [44] Tetrahedron, 2012, vol. 68, # 25, p. 5053 - 5059 [45] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 4, p. 909 - 912 [46] Organic and Biomolecular Chemistry, 2013, vol. 11, # 6, p. 1001 - 1006 [47] Journal of the Korean Chemical Society, 2012, vol. 56, # 6, p. 712 - 715 [48] ChemPlusChem, 2015, vol. 80, # 4, p. 731 - 739 [49] Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7154 - 7168 [50] Chemical Communications, 2014, vol. 50, # 8, p. 948 - 950 [51] Chemical Communications, 2014, vol. 50, # 64, p. 8934 - 8936 [52] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 170 - 177 [53] Journal of Catalysis, 2014, vol. 317, p. 1 - 10 [54] Chemical Science, 2014, vol. 5, # 11, p. 4517 - 4524 [55] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 28, p. 4699 - 4707 [56] Dyes and Pigments, 2016, vol. 126, p. 62 - 75 [57] Polymer, 2017, vol. 112, p. 342 - 350 [58] Organic Letters, 2018, vol. 20, # 7, p. 1970 - 1973 [59] Synthetic Communications, 2018, vol. 48, # 17, p. 2169 - 2176