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180468-42-2

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Basic Information
CAS No.: 180468-42-2
Name: Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate
Article Data: 23
Molecular Structure:
Molecular Structure of 180468-42-2 (Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate)
Formula: C18H19NO2
Molecular Weight: 281.354
Synonyms: 2(1H)-Isoquinolinecarboxylicacid, 3,4-dihydro-1-phenyl-, ethyl ester, (S)-;2(1H)-Isoquinolinecarboxylicacid, 3,4-dihydro-1-phenyl-, ethyl ester, (1S)-;Ethyl (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;
Density: 1.145 g/cm3
Boiling Point: 412.2 °C at 760 mmHg
Flash Point: 203.1 °C
PSA: 29.54000
LogP: 3.72850
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Synthetic route
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chloroformic acid ethyl ester

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

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃;100%
With triethylamine In dichloromethane at 20℃; for 5h;99%
With potassium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 2h; Reagent/catalyst; Concentration;97.9%
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ethyl bromide

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carbon dioxide

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

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane at 25℃; under 750.075 Torr; for 5h;84%
...Expand

ethyl (S)-((2-(2-hydroxyethyl)phenyl)(phenyl)methyl)carbamate

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 12h; enantioselective reaction;71%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Cooling with ice;71%
52250-50-7

1-phenyl-3,4-dihydroisoquinoline

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / ethanol / 60 h / 20 °C
2: 100 percent / K2CO3 / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C
2.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate
2.2: 1.17 h / pH 8 - 9
3.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C
View Scheme
3278-14-6

N-phenethylbenzamide

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: P2O5; POCl3 / xylene / 2.5 h / Heating
2: NaBH4 / ethanol / 60 h / 20 °C
3: 100 percent / K2CO3 / CH2Cl2 / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: PPA / water / 4.25 h / 14.9 - 165 °C
1.2: 0.17 h / 28 - 42 °C / pH 2.1 - 7.12
2.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C
3.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate
3.2: 1.17 h / pH 8 - 9
4.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C
View Scheme
1035272-88-8

(S)-1,2,3,4-tetrahydro-1-phenyl-isoquinoline-2-carboxylic acid

541-41-3

chloroformic acid ethyl ester

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With sodium carbonate In water; toluene at 14.9 - 34.8℃; for 3h;
180272-45-1

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

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / -10 - 20 °C
2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C
2.2: 20 °C / pH 9 - 10
3.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate
4.1: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / dichloromethane / 0 - 25 °C
2.1: sodium hydroxide / ethanol / 75 - 80 °C
2.2: Cooling
3.1: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / -10 - 20 °C
2.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C
2.2: 20 °C / pH 9 - 10
3.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate
4.1: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / -10 - 20 °C
2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C
2.2: 20 °C / pH 9 - 10
3.1: D-tartaric acid / water / Resolution of racemate
3.2: 20 °C
4.1: acetone / 5 °C / Reflux
View Scheme
881834-78-2

4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide / ethanol / 75 - 80 °C
1.2: Cooling
2.1: triethylamine / dichloromethane / -10 - 20 °C
3.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C
3.2: 20 °C / pH 9 - 10
4.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate
5.1: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / ethanol / 75 - 80 °C
1.2: Cooling
2.1: acetone / 5 °C / Reflux
View Scheme
22990-19-8

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

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate
2: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: D-tartaric acid / water / Resolution of racemate
1.2: 20 °C
2.1: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: D-tartaric acid / water / Resolution of racemate
1.2: 20 °C
2.1: potassium carbonate / dichloromethane / 0 - 25 °C
3.1: sodium hydroxide / ethanol / 75 - 80 °C
3.2: Cooling
4.1: acetone / 5 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: D-tartaric acid / methanol; ethyl acetate / 2.08 h / 28 - 64 °C / Resolution of racemate
1.2: 1.17 h / pH 8 - 9
2.1: sodium carbonate / toluene / 2.17 h / 0 - 28 °C
View Scheme
1300713-32-9

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

180468-42-2

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; water; phosphoric acid / 32 h / 95 - 100 °C
1.2: 20 °C / pH 9 - 10
2.1: D-tartaric acid / water / 1.5 h / 65 - 95 °C / Resolution of racemate
3.1: acetone / 5 °C / Reflux
View Scheme
Raw Materials
3297-72-1
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1609-47-8
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Downstream Products
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242478-37-1
22990-19-8
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  • (S)-ethyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

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    180468-42-2

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Chemistry

Molecule structure of Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate (CAS NO.180468-42-2):

Molecular Formula: C18H19NO2
Molecular Weight: 281.35 g/mol 
Density: 1.145 g/cm3 
Boiling Point: 412.162 °C at 760 mmHg
Flash Point: 203.068 °C
Index of Refraction: 1.582
Molar Refractivity: 82.021 cm3
Molar Volume: 245.628 cm3
Surface Tension: 45.057 dyne/cm 
Enthalpy of Vaporization: 66.475 kJ/mol 
InChI: InChI=1/C18H19NO2/c1-2-21-18(20)19-13-12-14-8-6-7-11-16(14)17(19)15-9-4-3-5-10-15/h3-11,17H,2,12-13H2,1H3 
InChIKey of Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate (CAS NO.180468-42-2): DKKVDRQVNMALLN-UHFFFAOYAI 

Specification

 Ethyl (S)-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate (CAS NO.180468-42-2) is also named as 2(1H)-isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-, ethyl ester ; Ethyl-1-phenyl-3,4-dihydroisochinolin-2(1H)-carboxylat ; (S)-ethyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate .