Products Categories
CAS No.: | 6790-63-2 |
---|---|
Name: | (3S)-7-Bromo-2,3,3a,8b-tetrahydro-3,3aβ,6,8bβ-tetramethyl-1H-cyclopenta[b]benzofuran |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C15H19BrO |
Molecular Weight: | 295.219 |
Synonyms: | (-)-ankorine; |
Density: | 1.307g/cm3 |
Boiling Point: | 335.1°Cat760mmHg |
Flash Point: | 131.7°C |
PSA: | 9.23000 |
LogP: | 4.59620 |
(-)-Debromoaplysin
(-)-Aplysin
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrachloromethane Heating; | 87% |
With bromine; sodium hydrogencarbonate In chloroform for 0.166667h; Ambient temperature; | 84% |
With bromine In chloroform at 0 - 20℃; for 0.166667h; | 81% |
With bromine; sodium carbonate In hexane for 0.0333333h; |
laurinterol
(-)-Aplysin
Conditions | Yield |
---|---|
With hydrogen bromide In diethyl ether at 20℃; for 0.25h; |
(3aS,8bS)-(-)-3a,8b-Dihydro-3,3a,6,8b-tetramethyl-1H-cyclopentabenzofuran
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 79 percent / H2 / PtO2 / ethanol / 3 h / Ambient temperature 2: 84 percent / NaHCO3, Br2 / CHCl3 / 0.17 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 83 percent / H2 / PtO2 / ethanol 2: 87 percent / N-bromosuccinimide / CCl4 / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 2: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
1-(methoxymethoxy)-3-methylbenzene
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 2: 90.5 percent / NaH / diethyl ether; dimethylformamide / 0.5 h 3: 37 percent / 1.) n-Butyllithium / diethyl ether / 1.) 15 min, 0 deg C, 2.) 10 min 4: 52 percent / KOH / methanol / 84 h / Heating 5: PCl3 / diethyl ether / 0.17 h 6: 96 percent / diethyl ether 7: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 8: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 9: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 9 steps 2: 90.5 percent / NaH / diethyl ether; dimethylformamide / 0.5 h 3: 37 percent / 1.) n-Butyllithium / diethyl ether / 1.) 15 min, 0 deg C, 2.) 10 min 4: 52 percent / KOH / methanol / 84 h / Heating 5: PBr3 / diethyl ether / 1 h 6: diethyl ether / 1 h 7: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 8: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 9: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
2-bromo-5-methylphenol
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90.5 percent / NaH / diethyl ether; dimethylformamide / 0.5 h 2: 37 percent / 1.) n-Butyllithium / diethyl ether / 1.) 15 min, 0 deg C, 2.) 10 min 3: 52 percent / KOH / methanol / 84 h / Heating 4: PCl3 / diethyl ether / 0.17 h 5: 96 percent / diethyl ether 6: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 7: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 8: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 8 steps 1: 90.5 percent / NaH / diethyl ether; dimethylformamide / 0.5 h 2: 37 percent / 1.) n-Butyllithium / diethyl ether / 1.) 15 min, 0 deg C, 2.) 10 min 3: 52 percent / KOH / methanol / 84 h / Heating 4: PBr3 / diethyl ether / 1 h 5: diethyl ether / 1 h 6: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 7: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 8: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
(-)-3-Methylphenyl(Isopinocampheyloxy)methyl Ether
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) tert-Butyllithium, TMEDA / 1.) Pentan, room temp., 0.5 h, 2.) 0 deg C, ether, 15 min 2: 52 percent / KOH / methanol / 84 h / Heating 3: PCl3 / diethyl ether / 0.17 h 4: 96 percent / diethyl ether 5: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 6: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 7: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 7 steps 1: 1.) tert-Butyllithium, TMEDA / 1.) Pentan, room temp., 0.5 h, 2.) 0 deg C, ether, 15 min 2: 52 percent / KOH / methanol / 84 h / Heating 3: PBr3 / diethyl ether / 1 h 4: diethyl ether / 1 h 5: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 6: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 7: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
(-)-2-Bromo-5-methylphenyl (Isopinocampheyloxy)methyl Ether
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 37 percent / 1.) n-Butyllithium / diethyl ether / 1.) 15 min, 0 deg C, 2.) 10 min 2: 52 percent / KOH / methanol / 84 h / Heating 3: PCl3 / diethyl ether / 0.17 h 4: 96 percent / diethyl ether 5: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 6: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 7: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 7 steps 1: 37 percent / 1.) n-Butyllithium / diethyl ether / 1.) 15 min, 0 deg C, 2.) 10 min 2: 52 percent / KOH / methanol / 84 h / Heating 3: PBr3 / diethyl ether / 1 h 4: diethyl ether / 1 h 5: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 6: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 7: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
(-)-8b-Hydroxy-3a,8b-dihydro-3,3a,6-trimethyl-3H-cyclopentabenzofuran
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: PCl3 / diethyl ether / 0.17 h 2: 96 percent / diethyl ether 3: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 4: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 5: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 5 steps 1: PBr3 / diethyl ether / 1 h 2: diethyl ether / 1 h 3: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 4: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 5: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
(1R,4R,5R)-5-Chloro-4,5-dimethyl-1-[4-methyl-2-((1R,2R,3R,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yloxymethoxy)-phenyl]-cyclopent-2-enol
(-)-Aplysin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 52 percent / KOH / methanol / 84 h / Heating 2: PCl3 / diethyl ether / 0.17 h 3: 96 percent / diethyl ether 4: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 5: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 6: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 6 steps 1: 52 percent / KOH / methanol / 84 h / Heating 2: PBr3 / diethyl ether / 1 h 3: diethyl ether / 1 h 4: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 5: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 6: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 92 percent / NaH / diethyl ether; dimethylformamide / 0.17 h 2: 1.) tert-Butyllithium, TMEDA / 1.) Pentan, room temp., 0.5 h, 2.) 0 deg C, ether, 15 min 3: 52 percent / KOH / methanol / 84 h / Heating 4: PCl3 / diethyl ether / 0.17 h 5: 96 percent / diethyl ether 6: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 7: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 8: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme | |
Multi-step reaction with 8 steps 1: 92 percent / NaH / diethyl ether; dimethylformamide / 0.17 h 2: 1.) tert-Butyllithium, TMEDA / 1.) Pentan, room temp., 0.5 h, 2.) 0 deg C, ether, 15 min 3: 52 percent / KOH / methanol / 84 h / Heating 4: PBr3 / diethyl ether / 1 h 5: diethyl ether / 1 h 6: 41 percent / Triphenylphosphine / (Ph3P)3RhCl / toluene; various solvent(s) / 120 h / Heating 7: 69 percent / H2 / Adams's catalyst / ethanol / 2 h 8: Br2, anhydrous sodium carbonate / hexane / 0.03 h View Scheme |