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CAS No.: | 866783-12-2 |
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Name: | (S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)-N-MethylMethanaMine |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C12H17NO2 |
Molecular Weight: | 207.272 |
Synonyms: | (1S)-4,5-Dimethoxy-1-(Methylaminoethyl)Benzocyclobutane;(S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)-N-MethylMethanaMine;(S)-1-(3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)-N-MethylMethanaMine;1-[(7S)-3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]-N-methylmethanamine |
PSA: | 30.49000 |
LogP: | 1.95380 |
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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With sodium hydroxide In ethanol; dichloromethane; water at 20℃; for 1h; pH=10 - 11; | 99% |
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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With sodium hydroxide In dichloromethane; water at 20℃; for 1h; pH=10 - 11; | 96% |
ethyl {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}carbamate
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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Stage #1: ethyl {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}carbamate With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 15℃; | 93% |
(7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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Stage #1: (7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide With sodium tetrahydroborate; iodine In tetrahydrofuran for 24h; Reflux; Stage #2: With hydrogenchloride; water pH=3; | 90% |
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Reflux; | 46% |
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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With sodium hydroxide In water; ethyl acetate at 25℃; for 0.166667h; | n/a |
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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With sodium hydroxide In water |
3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: potassium hydroxide / ethanol / 5 h / Reflux 2.1: (R)-1-phenyl-ethyl-amine / isopropyl alcohol / 1 h / Reflux; Resolution of racemate 3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 20 °C 4.1: iodine; sodium tetrahydroborate / tetrahydrofuran / 24 h / Reflux 4.2: pH 3 View Scheme | |
Multi-step reaction with 5 steps 1.1: borane-THF / tetrahydrofuran / 12 h / 20 °C 1.2: 1 h 2.1: triethylamine / dichloromethane / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux 4.1: ethanol / Resolution of racemate 5.1: sodium hydroxide / ethyl acetate View Scheme | |
Multi-step reaction with 3 steps 1.1: nitrilase of Rhodococcus erythropolis NCIMB11215 / aq. phosphate buffer; dimethyl sulfoxide / 96 h / 30 °C / pH 7.3 / Enzymatic reaction 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 20 °C 2.2: 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Reflux View Scheme |
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: (R)-1-phenyl-ethyl-amine / isopropyl alcohol / 1 h / Reflux; Resolution of racemate 2.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 20 °C 3.1: iodine; sodium tetrahydroborate / tetrahydrofuran / 24 h / Reflux 3.2: pH 3 View Scheme |
1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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Multi-step reaction with 7 steps 1.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.25 h / -60 °C 1.2: 1 h 2.1: sodium amide / 2 h / 20 °C 3.1: borane-THF / tetrahydrofuran / 12 h / 20 °C 3.2: 1 h 4.1: triethylamine / dichloromethane / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux 6.1: ethanol / Resolution of racemate 7.1: sodium hydroxide / ethyl acetate View Scheme |
3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine
Conditions | Yield |
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Multi-step reaction with 6 steps 1.1: sodium amide / 2 h / 20 °C 2.1: borane-THF / tetrahydrofuran / 12 h / 20 °C 2.2: 1 h 3.1: triethylamine / dichloromethane / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux 5.1: ethanol / Resolution of racemate 6.1: sodium hydroxide / ethyl acetate View Scheme |