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CAS No.: | 72016-31-0 |
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Name: | Orellanine II |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C10H8N2O4 |
Molecular Weight: | 220.185 |
Synonyms: | (2,2'-Bipyridine)-3,3',4,4'-tetrol;3,3'-dihydroxy-1H,1'H-[2,2']bipyridinyl-4,4'-dione; |
Density: | 1.684g/cm3 |
Boiling Point: | 257.4°Cat760mmHg |
Flash Point: | 109.5°C |
PSA: | 106.18000 |
LogP: | 0.14140 |
3,3',4,4'-tetramethoxy-2,2'-bipyridine
orelline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 5h; Heating; | 77% |
With hydrogen bromide at 150℃; sealed tube, overnight; | 60% |
With hydrogen bromide at 120℃; | 60% |
3,3'-Bis<<2-(trimethylsilyl)ethoxy>methoxy>-2,2'-bipyridin-4,4'-diol
orelline
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 1h; Heating; | 75% |
4,4'-dihydroxy-3,3'-dimethoxy-2,2'-bipyridine
orelline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 5h; Heating; | 71% |
3,3'-dihyroxy-4,4'-dimethoxy-2,2'-bipyridyl
orelline
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 5h; Heating; | 70% |
3,3',4,4'-tetrahydroxy-2,2'-bipyridine-1,1'-dioxide
orelline
Conditions | Yield |
---|---|
at 220℃; under 0.01 Torr; sublimation; | 50% |
for 336h; Irradiation; |
3,3'-Dihydroxy-2,2'-bipyridin-4,4'-dicarbaldehyd
orelline
Conditions | Yield |
---|---|
With dihydrogen peroxide In potassium hydroxide at 60 - 70℃; for 1h; | 36% |
orelline
Conditions | Yield |
---|---|
With bis-trimethylsilanyl peroxide In diethyl ether for 0.5h; Ambient temperature; | 11% |
Multi-step reaction with 3 steps 1: 45 percent / 0.5 h / -20 - -15 °C 2: 75 percent / conc. HCl / H2O / 30 h / Heating 3: 36 percent / 30percent H2O2 / aq. KOH / 1 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 10 percent / 0.5 h / -5 °C 2: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 10 percent / bis(trimethylsilyl)-peroxide / 0.5 h / -5 °C 2: 75 percent / 2N HCl / methanol / 1 h / Heating View Scheme |
2-iodo-3-hydroxypyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 70 percent / NaH / dimethylsulfoxide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 5.1: aq. HCl / diethyl ether / 15 h / 20 °C 6.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 4.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 5.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 6.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1.1: 85 percent / MeONa / dimethylformamide / 15 h / 0 - 20 °C 2.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 2.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 2.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 4.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 4.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 4.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 5.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-methoxy-pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 1.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 2.1: 69 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 3.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 3.3: [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 4.1: aq. HCl / tetrahydrofuran / 7 h / 50 °C 5.1: 71 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 1.3: 63 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 2.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -75 °C 3.2: ZnCl2 / tetrahydrofuran; hexane / -75 - 20 °C 3.3: 59 percent / [Pd(PPh3)4] / tetrahydrofuran; hexane / 20 h / Heating 4.1: 77 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |
2-iodo-3-(methoxymethoxy)pyridine
orelline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 2,2,6,6-tetramethylpiperidine; BuLi / tetrahydrofuran; hexane / 1 h / -50 °C 1.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h / -75 °C 1.3: 78 percent / aq. AcOH; AcOOH / tetrahydrofuran; hexane / -75 - 20 °C 2.1: 71 percent / Ag2CO3 / tetrahydrofuran / 15 h / 20 °C 3.1: [Pd(PPh3)4]; CuBr / dioxane / 15 h / Heating 4.1: aq. HCl / diethyl ether / 15 h / 20 °C 5.1: 70 percent / aq. HBr / acetic acid / 5 h / Heating View Scheme |