化学合成。
医药
合成路线 1（1. 合成：5220-49-5）
产率：93.6%
合成条件：at 110℃; for 0.25 h;
实验步骤：将1,3-环己二酮（0.03mol）和乙酸铵（0.039mol）加入100ml三颈烧瓶中，搅拌均匀，在110°C油浴中反应条件15min，取出油浴，然后自然 冷却，在此期间反应液体固化。 冷却至室温后，加入乙酸乙酯（10ml），加热溶解并冷却至0℃，过滤，干燥滤饼，得到3-氨基-2-环己烯酮的黄色晶体（产率93.6％）
参考文献：
- [1] New Journal of Chemistry, 2005, vol. 29, # 6, p. 769 - 772 [2] Patent: CN107337639, 2017, A. Location in patent: Paragraph 0120; 0123; 0135; 0144-0146; 0157; 0168; 0179 [3] Synlett, 2009, # 5, p. 818 - 822 [4] Synthetic Communications, 1998, vol. 28, # 7, p. 1197 - 1200 [5] Tetrahedron, 2003, vol. 59, # 43, p. 8589 - 8595 [6] Advanced Synthesis and Catalysis, 2010, vol. 352, # 6, p. 1055 - 1062 [7] Organic and Biomolecular Chemistry, 2010, vol. 8, # 15, p. 3464 - 3471 [8] Patent: US2011/98311, 2011, A1 [9] Patent: US2012/309758, 2012, A1 [10] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0371 [11] Patent: US2008/176308, 2008, A1. Location in patent: Page/Page column 11 [12] Tetrahedron Letters, 2004, vol. 45, # 25, p. 4911 - 4915 [13] Patent: CN108218770, 2018, A. Location in patent: Paragraph 0056-0065 [14] Patent: US2014/31391, 2014, A1. Location in patent: Paragraph 0362; 0363; 0364 [15] Synlett, 2010, # 2, p. 231 - 234 [16] Synlett, 2014, vol. 25, # 10, p. 1443 - 1447 [17] Patent: EP2650284, 2013, A1. Location in patent: Paragraph 0189 [18] Archives of Pharmacal Research, 2013, vol. 36, # 4, p. 436 - 447 [19] Patent: WO2012/52451, 2012, A1. Location in patent: Page/Page column 102-103 [20] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 11, p. 2415 - 2425 [21] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 685 - 690 [22] Patent: US5206367, 1993, A [23] Patent: US4952694, 1990, A [24] Patent: WO2009/55437, 2009, A2. Location in patent: Page/Page column 60; 61 [25] Synthesis, 2009, # 6, p. 985 - 999 [26] Patent: US2012/309758, 2012, A1. Location in patent: Page/Page column 63 [27] Advanced Synthesis and Catalysis, 2013, vol. 355, # 13, p. 2550 - 2557 [28] Tetrahedron Letters, 2014, vol. 55, # 10, p. 1686 - 1688 [29] Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4571 - 4575 [30] Heterocycles, 2014, vol. 89, # 6, p. 1427 - 1440 [31] Research on Chemical Intermediates, 2016, vol. 42, # 4, p. 3413 - 3423 [32] Tetrahedron Letters, 2018, vol. 59, # 32, p. 3069 - 3076
合成路线 2（2. 合成：5220-49-5）
产率：55%
合成条件：With tert.-butylhydroperoxide; copper diacetate In water at 30℃; for 12 h;
实验步骤：一般步骤：N-苄基烯胺酮（1.0mmol），二烷基乙炔二羧酸酯（1.0mmol），芳基或烷基胺（1.0mmol），Cu（OAc）2（8mol％）和TBHP（4.0mmol，0.56mL）的混合物 将70％水溶液（0.5mL）在空气中于30℃搅拌12小时。 通过TLC监测反应进程。 反应完成后，滤出固体并用热乙酸乙酯洗涤。 最后，在真空下除去滤液的溶剂，并通过柱色谱法在60-120目硅胶[乙酸乙酯/石油醚（60-80℃）]上纯化得到的粗产物。
参考文献：
- [1] Tetrahedron Letters, 2018, vol. 59, # 32, p. 3069 - 3076
