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180272-45-1

Basic Information
CAS No.: 180272-45-1
Name: (1R)-Phenyl-1,2,3,4-tetrahydroisoquinoline
Article Data: 45
Molecular Structure:
Molecular Structure of 180272-45-1 ((1R)-Phenyl-1,2,3,4-tetrahydroisoquinoline)
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
Synthetic route
220936-57-2

(R)-(+)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;99%
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.75h;68%
1443308-76-6

(R)-2-benzyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; under 760.051 Torr; for 24h; Schlenk technique;98%

C15H15N*C4H6O6

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With water; sodium hydroxide In ethyl acetate at 20℃;97.9%
3297-72-1

1-phenylisoquinoline

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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
52250-50-7

1-phenyl-3,4-dihydroisoquinoline

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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%
22990-19-8

1-phenyl-1,2,3,4-tetrahydroisoquinoline

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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;
22990-19-8

1-phenyl-1,2,3,4-tetrahydroisoquinoline

A

22990-19-8, 96719-89-0, 118864-75-8

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

B

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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
321670-05-7

(1R)-N-(8-menthyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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%
1346681-71-7

(1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one

22990-19-8

1-phenyl-1,2,3,4-tetrahydroisoquinoline

A

1346681-99-9

(1S)-2-(3-mesitylpropanoyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

B

22990-19-8, 96719-89-0, 118864-75-8

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

C

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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

(1R,5S)-1,3,8,8-Tetramethyl-5-((R)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-3-aza-bicyclo[3.2.1]octane-2,4-dione

180272-45-1

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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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  • (R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline CAS No.180272-45-1

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Specification

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