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CAS No.: | 180272-45-1 |
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Name: | (1R)-Phenyl-1,2,3,4-tetrahydroisoquinoline |
Article Data: | 45 |
Molecular Structure: | |
Formula: | C15H15N |
Molecular Weight: | 209.291 |
Synonyms: | (1R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline; |
Density: | 1.065 g/cm3 |
Melting Point: | 78-79℃ |
Boiling Point: | 338.4 °C at 760 mmHg |
Flash Point: | 166.9 °C |
PSA: | 12.03000 |
LogP: | 3.25050 |
(R)-(+)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
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With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 99% |
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.75h; | 68% |
(R)-2-benzyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; under 760.051 Torr; for 24h; Schlenk technique; | 98% |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethyl acetate at 20℃; | 97.9% |
1-phenylisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
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With bis(1,5-cyclooctadiene)diiridium(I) dichloride; trichloroisocyanuric acid; hydrogen; (R)-segphos In tetrahydrofuran at 80℃; under 62059.4 Torr; for 48h; Catalytic behavior; Reagent/catalyst; Solvent; Autoclave; enantioselective reaction; | 96% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; trichloroisocyanuric acid; hydrogen; (R)-segphos In tetrahydrofuran at 80℃; under 62059.4 Torr; for 48h; Catalytic behavior; Reagent/catalyst; Solvent; Glovebox; Autoclave; | 96% |
Multi-step reaction with 3 steps 1: acetone / 24 h / 90 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (Rax,S,S)-C3-TunePhos / dichloromethane; tetrahydrofuran / 20 h / 30 °C / 31029.7 Torr / Autoclave; Glovebox 3: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique View Scheme | |
Multi-step reaction with 3 steps 1: acetone / 24 h / 90 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) / dichloromethane; tetrahydrofuran / 20 h / 30 °C / 31029.7 Torr / Autoclave; Glovebox 3: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique View Scheme |
1-phenyl-3,4-dihydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
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Stage #1: 1-phenyl-3,4-dihydroisoquinoline With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With hydrogen In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; enantioselective reaction; | 94% |
With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; sodium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; Glovebox; enantioselective reaction; | 94% |
With N-Bromosuccinimide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; Glovebox; enantioselective reaction; | 94% |
1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: 1-phenyl-1,2,3,4-tetrahydroisoquinoline With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With hydrogen In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; enantioselective reaction; | 93% |
With L-(-)-tartaric acid In methanol Resolution of racemate; | |
With potassium hydroxide In water; dimethyl sulfoxide for 11.8333h; Purification / work up; Heating / reflux; |
1-phenyl-1,2,3,4-tetrahydroisoquinoline
A
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With borane-ammonia complex; 6-hydroxy-D-nicotine oxidase E350L/E352D mutant for 120h; Kinetics; Enzymatic reaction; enantioselective reaction; | A n/a B 86% |
With D-tartaric acid Resolution of racemate; | A 79% B 2.78 g |
Stage #1: 1-phenyl-1,2,3,4-tetrahydroisoquinoline With D-tartaric acid In water Resolution of racemate; Stage #2: With sodium hydroxide In water at 20℃; Purification / work up; | A n/a B n/a |
(1R)-N-(8-menthyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: (1R)-N-(8-menthyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline With 3 A molecular sieve; sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 48h; Stage #2: With potassium hydroxide In tetrahydrofuran Further stages.; | 82% |
(1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one
1-phenyl-1,2,3,4-tetrahydroisoquinoline
A
(1S)-2-(3-mesitylpropanoyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
C
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 23℃; for 18h; Inert atmosphere; Resolution of racemate; optical yield given as %ee; enantioselective reaction; | A 49% B n/a C n/a |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
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With lithium aluminium tetrahydride In diethyl ether at 0℃; for 48h; | 42% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 48h; Yield given; |
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The chemical with CAS registry number of 180272-45-1 is known as Isoquinoline, 1,2,3,4-tetrahydro-1-phenyl-, (1R)-. The systematic name is (1R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline. In addition, the formula is C15H15N and the molecular weight is 209.29.
Physical properties about Isoquinoline, 1,2,3,4-tetrahydro-1-phenyl-, (1R)- are: (1)ACD/LogP: 2.70; (2)ACD/LogD (pH 5.5): -0.22; (3)ACD/LogD (pH 7.4): 1.19; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 2.06; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 21.75; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.589; (12)Molar Refractivity: 66.21 cm3; (13)Molar Volume: 196.4 cm3; (14)Surface Tension: 41.8 dyne/cm; (15)Density: 1.065 g/cm3; (16)Flash Point: 166.9 °C; (17)Enthalpy of Vaporization: 58.17 kJ/mol; (18)Boiling Point: 338.4 °C at 760 mmHg; (19)Vapour Pressure: 9.87E-05 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
1. SMILES: c1ccc3c(c1)[C@@H](c2ccccc2)NCC3
2. InChI: InChI=1/C15H15N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-9,15-16H,10-11H2/t15-/m1/s1
3. InChIKey: PRTRSEDVLBBFJZ-OAHLLOKOBF
4. Std. InChI: InChI=1S/C15H15N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-9,15-16H,10-11H2/t15-/m1/s1
5. Std. InChIKey: PRTRSEDVLBBFJZ-OAHLLOKOSA-N