2,4-二甲氧基-3-甲基苯甲醛合成路线 （共 22 条）
反应条件
1.1: m-CPBA; p-TsOH / CH2Cl2 / 7 h / 20 °C 1.2: 99 percent / K2CO3 / CH2Cl2; methanol / 4 h / 20 °C 2.1: 81 percent / Br2; K2CO3 / CH2Cl2 / 2 h / -78 °C View Scheme
参考文献
Zhou, Bishan; Guo, Jinsong; Danishefsky, Samuel J.
Organic Letters, 2002 , vol. 4, # 1 p. 43 - 45
反应条件
1: MCPBA / CH2Cl2 / 5 h / 20 °C 2: aq. NaOH / methanol / 4 h / 20 °C 3: aq. CAN / acetonitrile / 1 h / 20 °C 4: aq. Na2S2O4 / acetonitrile / 4 h / 20 °C View Scheme
参考文献
Heckrodt, Thilo J.; Mulzer, Johann
Journal of the American Chemical Society, 2003 , vol. 125, # 16 p. 4680 - 4681
反应条件
1: 30percent H2O2, SeO2, t-BuOH / 50 - 60 °C 2: Et3N, MeOH / Ambient temperature 3: pyridine / Ambient temperature 4: 90percent HNO3, Ac2O, Hg(OAc)2 / acetic acid / 0 °C 5: 3N NaOH / methanol / Ambient temperature View Scheme
参考文献
Fukuyama, Tohru; Yang, Lihu
Tetrahedron Letters, 1986 , vol. 27, # 52 p. 6299 - 6300
反应条件
1.1: m-CPBA; TsOH / CH2Cl2 / 20 °C
2.1: K2CO3 / CH2Cl2; methanol
3.1: 60 percent / acetic acid / Heating
4.1: 97 percent / K2CO3; Br2 / CH2Cl2 / 1 h / 0 °C
5.1: 94 percent / diisopropylethylamine / dimethylformamide / 1.5 h / 20 °C
6.1: 77 percent / i-PrOTMS; TMSOTf / CH2Cl2 / -78 °C
7.1: 85 percent / tetrahydrofuran / 24 h / Heating
8.1: 85 percent / Me2AlCl / CH2Cl2 / 0.17 h / -78 °C
9.1: LHMDS / tetrahydrofuran; hexane / 1.5 h / -78 - -10 °C
9.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C
10.1: 81 percent / NaBH4 / ethanol / 2.5 h / -78 °C
11.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / -10 °C
12.1: n-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C
12.2: BF3*Et2O / tetrahydrofuran; pentane / 3 h / -78 °C
13.1: 57 percent / second generation Grubbs' catalyst / CH2Cl2 / 48 h / 50 - 55 °C
14.1: 89 percent / 2,6-lutidine; DMAP / pyridine / 1 h / 0 - 20 °C
15.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C
16.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C
17.1: 84 percent / BnNMe3OH / methanol; tetrahydrofuran / 1 h / 0 °C
18.1: n-BuLi; WCl6 / tetrahydrofuran; hexane / 0 - 20 °C
19.1: 12 mg / pyridinum p-toluenesulfonate / methanol / 6 h / 0 °C
20.1: 69 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0 - 20 °C
21.1: 40 percent / aq. HF / acetonitrile / 0 - 20 °C
View Scheme
参考文献
Smith III, Amos B.; Mesaros, Eugen F.; Meyer, Emmanuel A.
Journal of the American Chemical Society, 2006 , vol. 128, # 15 p. 5292 - 5299
反应条件
1.1: 83 percent / BBr3 / CH2Cl2 / -78 - 20 °C
2.1: 99 percent / K2CO3 / dimethylformamide / 4 h / 60 °C
3.1: 88 percent / mCPBA / CH2Cl2 / 1 h / 60 °C
4.1: 53 percent / AcOH / 3 h / 110 °C
5.1: 81 percent / pyridine / CH2Cl2 / 1 h / cooling
6.1: 90 percent / Et4NCl; PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 110 °C
7.1: Mg; 1,2-dibromoethane / tetrahydrofuran
7.2: tetrahydrofuran / 2 h / 20 °C
7.3: 87 percent / H2O2; KHCO3; KF / tetrahydrofuran; methanol / 3 h / 20 °C
8.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C
9.1: 85 percent / pyridinium chlorochromate; celite / CH2Cl2 / 10 h / 20 °C
10.1: 57 percent / NH2OH*HCl; AcONa / ethanol / 1 h / 85 °C
11.1: 49 percent / various solvent(s) / 1 h / 180 °C
12.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
13.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling
13.2: 78 percent / cyclohexane; diethyl ether; dioxane / 12 h / 20 °C
14.1: 96 percent / BF3*Et2O; Me2S / CH2Cl2 / 18 h / 20 °C
15.1: 95 percent / salcomine; O2 / dimethylformamide / 2 h / 20 °C
View Scheme
参考文献
Kuwabara, Nagako; Hayashi, Hiroyuki; Hiramatsu, Noriko; Choshi, Tominari; Kumemura, Teppei; Nobuhiro, Junko; Hibino, Satoshi
Tetrahedron, 2004 , vol. 60, # 13 p. 2943 - 2952
反应条件
1.1: 83 percent / BBr3 / CH2Cl2 / -78 - 20 °C
2.1: 99 percent / K2CO3 / dimethylformamide / 4 h / 60 °C
3.1: 88 percent / mCPBA / CH2Cl2 / 1 h / 60 °C
4.1: 53 percent / AcOH / 3 h / 110 °C
5.1: 81 percent / pyridine / CH2Cl2 / 1 h / cooling
6.1: 90 percent / Et4NCl; PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 110 °C
7.1: Mg; 1,2-dibromoethane / tetrahydrofuran
7.2: tetrahydrofuran / 2 h / 20 °C
7.3: 87 percent / H2O2; KHCO3; KF / tetrahydrofuran; methanol / 3 h / 20 °C
8.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C
9.1: 85 percent / pyridinium chlorochromate; celite / CH2Cl2 / 10 h / 20 °C
10.1: 57 percent / NH2OH*HCl; AcONa / ethanol / 1 h / 85 °C
11.1: 49 percent / various solvent(s) / 1 h / 180 °C
12.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
13.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling
13.2: 64 percent / cyclohexane; diethyl ether; dioxane / 0.5 h / 20 °C
14.1: 81 percent / NaN3 / H2O; dioxane / 1 h / 60 °C
15.1: PPh3 / benzene / 12 h / 20 °C
15.2: 45 percent / benzene / 0.08 h / 20 °C
16.1: 91 percent / H2 / Pd/C / ethanol / 2 h / 20 °C
17.1: 85 percent / salcomine; O2 / dimethylformamide / 2 h / 20 °C
View Scheme
参考文献
Kuwabara, Nagako; Hayashi, Hiroyuki; Hiramatsu, Noriko; Choshi, Tominari; Kumemura, Teppei; Nobuhiro, Junko; Hibino, Satoshi
Tetrahedron, 2004 , vol. 60, # 13 p. 2943 - 2952
反应条件
1.1: 94 percent / Cu(NO3)2*3H2O
2.1: H2 / Raney Nickel / tetrahydrofuran; H2O / 20 °C
3.1: 92 percent / NBS / CHCl3 / 0.08 h / 20 °C
4.1: HCl; NaNO2 / tetrahydrofuran; H2O
4.2: 89 percent / urea; H3PO2 / tetrahydrofuran; H2O
5.1: 87 percent / PCC / CH2Cl2 / 0 - 20 °C
6.1: 94 percent / BBr3 / CH2Cl2 / -78 - 20 °C
View Scheme
参考文献
Zhu, Jianglong; Germain, Andrew R.; Porco Jr., John A.
Angewandte Chemie - International Edition, 2004 , vol. 43, # 10 p. 1239 - 1243
反应条件
1.1: 85 percent / Cu(NO3)2*3H2O / 20 °C
2.1: H2 / Pd/C / tetrahydrofuran / 20 °C
3.1: Br2; AcOH / 20 °C
4.1: NaNO2; aq. HCl / tetrahydrofuran / -5 °C
4.2: 87 percent / H3PO2 / 0 - 40 °C
5.1: 95 percent / BBr3 / CH2Cl2 / -78 - 20 °C
6.1: 68 percent / Pd(PPh3)2Cl2; CuI; Et3N / 1,2-dimethoxy-ethane / 0.42 h / 120 °C / microwave irradiation
View Scheme
参考文献
Zhu, Jianglong; Germain, Andrew R.; Porco Jr., John A.
Angewandte Chemie - International Edition, 2004 , vol. 43, # 10 p. 1239 - 1243
反应条件
1: m-CPBA; TsOH / CH2Cl2 / 20 °C
2: K2CO3 / CH2Cl2; methanol
3: 60 percent / acetic acid / Heating
View Scheme
参考文献
Smith III, Amos B.; Mesaros, Eugen F.; Meyer, Emmanuel A.
Journal of the American Chemical Society, 2006 , vol. 128, # 15 p. 5292 - 5299
反应条件
1: 97 percent / hydrazine hydrate, potasium hydroxide / various solvent(s) / 2 h / 150 °C
2: 90 percent / boron trichloride / CH2Cl2 / 23 h / Ambient temperature
View Scheme
参考文献
Carvalho, Christopher F.; Russo, Albert V.; Sargent, Melvyn V.
Australian Journal of Chemistry, 1985 , vol. 38, # 5 p. 777 - 792
