- 制备
1-溴甲基萘是一种化学物质,其可由1-甲基萘经N-溴代琥珀酰亚胺(NBS)光溴化反应制得。
- 化学性质
白色固体粉末。
未明确提及具体应用领域
合成路线 1(1. 合成:3163-27-7)
产率:99%
合成条件:With ethyl 2,2-dibromoacetoacetate; triphenylphosphine In dichloromethane at 20℃; for 0.50 h;
实验步骤:通用方法:在环境温度下,将α,α-二乙酰乙酸乙酯2a(0.41mmol,1.2当量),醇1a-1s(0.34mmol,1.0当量)和Ph3P(0.68mmol,2.0当量)加入空气中的3mL DCE中。 在室温下搅拌适当的时间(通过TLC监测)后,通过加入H 2 O(3mL)淬灭反应,然后用乙酸乙酯(3×3mL)萃取。 将合并的有机层用盐水洗涤,用Na 2 SO 4干燥并浓缩。 通过硅胶柱色谱法纯化粗产物,用石油醚或石油醚和乙酸乙酯的混合物作为洗脱剂,得到相应的产物3a-3s。
参考文献:
- [1] Synthetic Communications, 2010, vol. 40, # 11, p. 1646 - 1649 [2] Organic Letters, 2003, vol. 5, # 8, p. 1167 - 1169 [3] Tetrahedron Letters, 2014, vol. 55, # 1, p. 90 - 93 [4] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641 [5] Tetrahedron, 2003, vol. 59, # 52, p. 10453 - 10463 [6] Bulletin of the Chemical Society of Ethiopia, 2012, vol. 26, # 2, p. 305 - 309 [7] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1648 - 1655 [8] Patent: WO2010/125350, 2010, A1. Location in patent: Page/Page column 53-54 [9] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1922, vol. 175, p. 105 [10] Journal of the American Chemical Society, 1933, vol. 55, p. 2975,2976 [11] Journal of the Chemical Society, 1957, p. 2796,2799 [12] Journal of the American Chemical Society, 1953, vol. 75, p. 353 [13] Patent: US5859007, 1999, A [14] Polish Journal of Chemistry, 2007, vol. 81, # 5-6, p. 947 - 969 [15] Tetrahedron Letters, 2011, vol. 52, # 1, p. 13 - 16 [16] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467 [17] Chemical Communications, 2014, vol. 50, # 28, p. 3692 - 3694 [18] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487 [19] Organic Letters, 2014, vol. 16, # 17, p. 4424 - 4427
合成路线 2(3. 合成:3163-27-7)
产率:80%
合成条件:With tribromo-isocyanuric acid In ethyl acetate for 6 h; Reflux; Green chemistry
实验步骤:通用程序:将芳烃(2.0mmol)和TBCA(0.25g,0.68mmol)的EtOAc(20mL)溶液在搅拌下回流6小时。 在反应结束时,然后通过过滤分离沉淀的氰尿酸,并将滤液在减压下蒸发至干。 将残余物通过短色谱柱(SiO 2,用15:1己烷 - 乙酸乙酯洗脱),得到纯化的产物。
参考文献:
- [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 11, p. 3355 - 3362 [2] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 2033 - 2038 [3] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865 [4] Monatshefte fur Chemie, 2003, vol. 134, # 7, p. 991 - 1014 [5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204 [6] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6843 - 6845 [7] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126 [8] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2589 - 2600 [9] Organic and Biomolecular Chemistry, 2016, vol. 14, # 15, p. 3699 - 3714 [10] Canadian Journal of Chemistry, 1985, vol. 63, p. 3140 - 3146 [11] Journal of the Chemical Society, 1927, p. 3104 [12] Chemische Berichte, 1922, vol. 55, p. 1854 [13] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 75 [14] Helvetica Chimica Acta, 1936, vol. 19, p. 581,586 [15] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 853,856 [16] Annales de Chimie (Cachan, France), 1948, vol. <12> 3, p. 62,84 [17] Journal of the Chemical Society, 1946, p. 830 [18] Chemische Berichte, 1916, vol. 49, p. 2823 [19] Chemische Berichte, 1909, vol. 42, p. 2381 [20] Chemische Berichte, 1926, vol. 59, p. 2511 [21] Chemische Berichte, 1927, vol. 60, p. 2371 [22] Il Farmaco; edizione scientifica, 1974, vol. 29, # 3, p. 217 - 224 [23] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1976, p. 1104 - 1111 [24] Journal of the American Chemical Society, 1975, vol. 97, # 8, p. 2198 - 2205 [25] Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1982, vol. 78, p. 3467 - 3476 [26] Chemical and pharmaceutical bulletin, 1994, vol. 42, # 3, p. 512 - 520 [27] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 2, p. 297 - 304 [28] Polish Journal of Chemistry, 2001, vol. 75, # 3, p. 429 - 441 [29] Synlett, 2005, # 18, p. 2837 - 2842 [30] Patent: WO2007/27917, 2007, A2. Location in patent: Page/Page column 28-29 [31] Synthetic Communications, 2010, vol. 40, # 17, p. 2617 - 2623 [32] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197 [33] Biochemical and Biophysical Research Communications, 2013, vol. 437, # 4, p. 620 - 624 [34] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410 [35] Patent: CN105218382, 2016, A. Location in patent: Paragraph 0044-0046