6-甲氧基-1-萘满酮合成路线 （共 219 条）
反应条件
sodium methylate; benzene
参考文献
Buchta; Galster; Luther
Chemische Berichte, 1949 , vol. 82, p. 126,130
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Bachmann; Thomas
Journal of the American Chemical Society, 1942 , vol. 64, p. 94,95
反应条件
toluene-4-sulfonic acid in tetrahydrofuran; methylene chloride-hexane; water; toluene
参考文献
Hoffman-La Roche Inc.
Patent: US4927838 A1, 1990 ;
反应条件
1: 1.) magnesium / 1.) THF, 2.) RT, 2 h
2: p-toluenesulfonic acid / toluene / 3 h / Heating
View Scheme
参考文献
Schneider; Schiller
Archiv der Pharmazie, 1990 , vol. 323, # 1 p. 17 - 21
反应条件
diethyl ether; benzene
Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit KHSO4 auf 160grad;
参考文献
Bergmann; Szmuszkowicz; Fawaz
Journal of the American Chemical Society, 1947 , vol. 69, p. 1773,1776
反应条件
1: NaOMe
2: pyridine
3: hydrogen / PtO2
4: Michael condensation
5: 20percent aq. KOH
6: 1.) ethyl chloroformate, triethylamine, 2.) sodium azide / 1.) acetone, 0 deg C, 30 min, 2.) H2O, 0 deg C, 1 h
7: toluene / 2 h / steam bath
8: HCl, AcOH / H2O / 24 h / Heating
View Scheme
参考文献
Bhattacharya, Sudin; Mandal, Asok N.; Chaudhuri, Swadesh R. Ray; Chatterjee, Amareshwar
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , # 1 p. 5 - 13
反应条件
1: 95 percent / tetrabutylammonium tribromide / methanol; CH2Cl2 / 20 °C
2: 50 percent / dimethylformamide / 20 °C
3: 83 percent / NaBH4 / methanol / 1 h / 20 °C
4: 54 percent / acetic acid; sulfuric acid / 4 h / 100 °C
View Scheme
参考文献
Voets, Marieke; Antes, Iris; Scherer, Christiane; Mueller-Vieira, Ursula; Biemel, Klaus; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 7 p. 2222 - 2231
反应条件
1: 95 percent / tetrabutylammonium tribromide / methanol; CH2Cl2 / 20 °C
2: 86 percent / NaBH4 / methanol; tetrahydrofuran / 0.75 h / 0 - 20 °C
3: 60 percent / p-toluenesulfonic acid / toluene / 2 h / Heating
View Scheme
参考文献
Voets, Marieke; Antes, Iris; Scherer, Christiane; Mueller-Vieira, Ursula; Biemel, Klaus; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 7 p. 2222 - 2231
反应条件
1: 1.) N-isopropylcyclohexylamine, n-butyllithium / 1.) THF, hexane, -75 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1.5 h
2: 10percent Pd/C, 1,1-diphenylethylene, 1-methylnaphthalene / 3 h / 250 - 260 °C
3: 93 percent / lithium aluminum hydride / diethyl ether / Ambient temperature
4: pyridine / 2 h / Ambient temperature
5: KBr, 18-crown-6 ether / acetone / Heating
6: 1.) Mg, 1,2-dibromoethane / 1.) ether, 1 h, 2.) ether, 5 deg C - 9 deg C, 4 h
7: 1.32 g / 30percent aq. H2O2, 6 N aq. NaOH / ethanol / 3 h / 20 °C
View Scheme
参考文献
Silverman, I. Robert; Daub, Guido H.; Jagt, David L. Vander
Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5550 - 5556
反应条件
1: 98 percent / lithium bromide / diethyl ether; tetrahydrofuran / Ambient temperature
2: sodium, liquid ammonia / ethanol
3: 71 percent / 10percent aq. HCl
4: 85 percent / diethyl ether / 0.5 h
5: 1.) sodium borohydride, 2.) 10percent aq. sodium hydroxide / 1.) abs. ethanol, 1 h
6: 64 percent / zinc dust, anhydrous copper(II) chloride / diethyl ether
7: 79.5 percent / Jones reagent / acetone / 1 h
8: 92.5 percent / sodium methoxide / benzene / 13 h / Ambient temperature
9: 1.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) conc aq. HCl / 1.) benzene, room temperature, 30 min, 2.) 22 h
10: 74 percent / anhydrous potassium carbonate / dimethylformamide / 2.5 h
11: 98 percent / toluene / 0.75 h
12: 49 percent / 10percent aq. HCl / diethyl ether / 25 h
View Scheme
参考文献
Marshall, James A.; Conrow, Raymond E.
Journal of the American Chemical Society, 1980 , vol. 102, # 12 p. 4274 - 4275
反应条件
1: methyl iodide With magnesium in diethyl ether
0.25 - 0.75 h;
2: 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one in tetrahydrofuran; diethyl ether
T=0 - 20°C; 2.25 h; Product distribution / selectivity;
参考文献
UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.
Patent: WO2006/133303 A1, 2006 ;
Location in patent: Page/Page column 78; 80 ;
