2-氯环己基-1-烯丙醛主要应用于医药和农药领域,具体用途未在提供的信息中详细说明。
医药; 农药
合成路线 1(1. 合成:1680-73-5)
产率:87%
合成条件:Stage #1: at 0 - 20℃; for 0.50 h; Stage #2: at 0 - 20℃; for 12 h;
实验步骤:在0℃下,在搅拌下,将三氯化磷(125g,815mmol)滴加到含有N,N-二甲基甲酰胺(74.5g,1019mmol)的火焰干燥的底部烧瓶中。 添加后,将混合物温热至环境温度30分钟,并再次冷却至0℃,然后滴加环己酮(50g,509mmol)。 将混合物温热至室温12小时。将反应物倒在冰上并用NaHCO 3淬灭。 中和后,将混合物用乙酸乙酯(100mL×3)萃取并用水和盐水洗涤。 将有机相干燥,过滤并浓缩,得到产物(160g,87%收率)。 1 H NMR:(CDCl 3,400MHz)δ1.741.75(m,2H),1.761.78(m,2H),2.24-2.27(m,2H),2.53~2.59(m,2H) ,7.25(s,1 H)。
参考文献:
- [1] Synlett, 2014, vol. 25, # 20, p. 2879 - 2882 [2] Organic Letters, 2014, vol. 16, # 17, p. 4662 - 4665 [3] Journal of Organometallic Chemistry, 2011, vol. 696, # 1, p. 179 - 187 [4] Patent: WO2013/43553, 2013, A1. Location in patent: Page/Page column 115 [5] Organic Letters, 2015, vol. 17, # 15, p. 3734 - 3737 [6] Organic Letters, 2010, vol. 12, # 12, p. 2884 - 2887 [7] Chemical Communications, 2011, vol. 47, # 36, p. 10133 - 10135 [8] Synthetic Communications, 2010, vol. 40, # 16, p. 2441 - 2456 [9] Organic Preparations and Procedures International, 2007, vol. 39, # 2, p. 195 - 199 [10] Chemical and Pharmaceutical Bulletin, 1972, vol. 20, # 2, p. 309 - 313 [11] Journal of the Chemical Society [Section] C: Organic, 1970, p. 2484 - 2488 [12] Tetrahedron Letters, 1977, p. 2027 - 2030 [13] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991, vol. 40, # 11, p. 2228 - 2234 [14] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, # 11, p. 2552 - 2558 [15] Canadian Journal of Chemistry, 1966, vol. 44, p. 45 - 51 [16] Chemische Berichte, 1960, vol. 93, p. 2743 - 2749 [17] Synthesis, 1985, # 5, p. 496 - 497 [18] Synthetic Communications, 1988, vol. 18, # 13, p. 1475 - 1482 [19] Journal of Organic Chemistry, 1994, vol. 59, # 12, p. 3341 - 3346 [20] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8400 - 8406 [21] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3736 - 3740 [22] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 63 - 69 [23] Synthesis, 2010, # 9, p. 1428 - 1430 [24] Patent: WO2010/141761, 2010, A2. Location in patent: Page/Page column 58 [25] Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1473 - 1479 [26] Chemical Communications, 2014, vol. 50, # 40, p. 5254 - 5257 [27] Journal of Organic Chemistry, 2014, vol. 79, # 13, p. 6037 - 6046 [28] Patent: WO2016/85939, 2016, A2. Location in patent: Paragraph 00198 [29] Organic Letters, 2018, vol. 20, # 4, p. 1252 - 1255 [30] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4247 - 4254