6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘合成路线 （共 16 条）
反应条件
aluminium trichloride in hexane 1.) RT, 30 min, 2.) reflux, 15 min;
参考文献
Boehm; Zhang; Badea; White; Mais; Berger; Suto; Goldman; Heyman
Journal of Medicinal Chemistry, 1994 , vol. 37, # 18 p. 2930 - 2941
反应条件
boron trifluoride diethyl etherate; bromine in dichloromethane T=0 - 20°C; Inert atmosphere;
参考文献
Christie, Victoria B.; Barnard, Jonathan H.; Batsanov, Andrei S.; Bridgens, Caroline E.; Cartmell, Emily B.; Collings, Jonathan C.; Maltman, Daniel J.; Redfern, Christopher P. F.; Marder, Todd B.; Przyborski, Stefan; Whiting, Andrew
Organic and Biomolecular Chemistry, 2008 , vol. 6, # 19 p. 3497 - 3507
反应条件
1: 56 percent / HCl gas / ethanol 2: 92 percent / AlCl3 / hexane / 1.) RT, 30 min, 2.) reflux, 15 min View Scheme
参考文献
Guerrero Jr., Palimecio G.; De Oliveira, Paulo R.; Baroni, Adriano C.M.; Marques, Francisco A.; Labes, Ricardo; Hurtado, Gabriela R.; Dabdoub, Miguel J.
Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5302 - 5305
反应条件
1: With sodium nitrate 2: With hydrogen bromide; copper(I) bromide in water
参考文献
Nakamura, Masaharu; Matsumoto, Yotaro; Toyama, Masaaki; Baba, Masanori; Hashimoto, Yuichi
Chemical and Pharmaceutical Bulletin, 2013 , vol. 61, # 2 p. 237 - 241
反应条件
1: 6-bromo-1,1,4,4-tetramethyl 1,2,3,4-tetrahydronaphthalene With n-butyllithium in tetrahydrofuran; hexane T=20°C; 1 h; 2: 1-bromo-butane in tetrahydrofuran; hexane T=20°C; 0.5 h;
参考文献
Cavasotto, Claudio N.; Liu, Gang; James, Sharon Y.; Hobbs, Peter D.; Peterson, Valerie J.; Bhattacharya, Ananyo A.; Kolluri, Siva K.; Zhang, Xiao-Kun; Leid, Mark; Abagyan, Ruben; Liddington, Robert C.; Dawson, Marcia I.
Journal of Medicinal Chemistry, 2004 , vol. 47, # 18 p. 4360 - 4372
反应条件
1.1: palladium dichloride; copper(l) iodide; triethylamine / methanol / 20 °C / |Sonication 2.1: sodium hydride / toluene / |Reflux 2.2: 20 °C 3.1: n-butyllithium / tetrahydrofuran / -78 °C 3.2: 20 °C 4.1: tetrahydrofuran; hexane / 0.17 h / 0 - 20 °C / |Inert atmosphere 4.2: 2 h / |Reflux; |Inert atmosphere 5.1: tetrahydrofuran; hexane / 0.17 h / -78 °C / |Inert atmosphere 6.1: tetrahydrofuran; hexane / 0.5 h / |Inert atmosphere 7.1: Cl2Ni(1,2-bis(diphenylphosphino)ethane) / tetrahydrofuran / 5 h / |Inert atmosphere; |Reflux 8.1: water; hydrogenchloride / 3 h / |Reflux View Scheme
参考文献
Guerrero Jr., Palimecio G.; De Oliveira, Paulo R.; Baroni, Adriano C.M.; Marques, Francisco A.; Labes, Ricardo; Hurtado, Gabriela R.; Dabdoub, Miguel J.
Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5302 - 5305
反应条件
hydrogenchloride; n-butyllithium in tetrahydrofuran; hexane
参考文献
Galderma Research and Development
Patent: US6316009 B1, 2001 ;
参考文献
Wisniewska, Hanna M.; Swift, Elizabeth C.; Jarvo, Elizabeth R.
Journal of the American Chemical Society, 2013 , vol. 135, # 24 p. 9083 - 9090
反应条件
potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine in N,N-dimethyl-formamide
T=80°C; Suzuki-Miyaura coupling; Inert atmosphere;
参考文献
Kim, Hye Ryung; Yun, Jaesook
Chemical Communications, 2011 , vol. 47, # 10 p. 2943 - 2945
反应条件
1.1: palladium dichloride; copper(l) iodide; triethylamine / methanol / 20 °C / |Sonication
2.1: sodium hydride / toluene / |Reflux
2.2: 20 °C
3.1: n-butyllithium / tetrahydrofuran / -78 °C
3.2: 20 °C
4.1: tetrahydrofuran; hexane / 0.17 h / 0 - 20 °C / |Inert atmosphere
4.2: 2 h / |Reflux; |Inert atmosphere
5.1: tetrahydrofuran; hexane / 0.17 h / -78 °C / |Inert atmosphere
6.1: tetrahydrofuran; hexane / 0.5 h / |Inert atmosphere
7.1: Cl2Ni(1,2-bis(diphenylphosphino)ethane) / tetrahydrofuran / 2.5 h / |Inert atmosphere; |Reflux
View Scheme
参考文献
Guerrero Jr., Palimecio G.; De Oliveira, Paulo R.; Baroni, Adriano C.M.; Marques, Francisco A.; Labes, Ricardo; Hurtado, Gabriela R.; Dabdoub, Miguel J.
Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5302 - 5305
