Conditions | Yield |
---|---|
With hydrogenchloride In water at 90℃; for 12h; Pictet-Spengler Synthesis; | 98% |
With hydrogenchloride In water at 90℃; for 12h; | 98% |
With hydrogenchloride at 85℃; for 9h; Pictet-Spengler condensation; | 95% |
(-)-menthyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
L-Tic-OH
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 6h; Ambient temperature; | 94% |
(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester
L-Tic-OH
Conditions | Yield |
---|---|
With sodium hydroxide In water for 15h; Ambient temperature; | 81% |
With hydrogen; palladium on activated charcoal In ethanol; water; acetic acid for 4h; Ambient temperature; | 75.4% |
(10aS)-3,3-Bis(trifluoromethyl)-1-oxo-(1,2,3,4-tetrahydroisoquinolino)[2,3-c]oxazolidine
L-Tic-OH
Conditions | Yield |
---|---|
With water In isopropyl alcohol at 20℃; | 72% |
(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
L-Tic-OH
Conditions | Yield |
---|---|
With ammonium hydroxide; borane-ammonia complex; recombinant Escherichia coli BL21 (DE3) cells expressed D-amino acid oxidase from Fusarium solani M-0718 In water at 30℃; pH=8; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | 68% |
(3R,10bS)-3-tert-Butyl-2-methyl-2,3,6,10b-tetrahydro-5H-imidazo[5,1-a]isoquinolin-1-one
L-Tic-OH
Conditions | Yield |
---|---|
With hydrogenchloride; Dowex 50-WX8; acetic acid In water; toluene at 103℃; for 126h; | 67% |
(3'S,4R,5S)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone
A
L-Tic-OH
B
(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Conditions | Yield |
---|---|
With water for 12h; Hydrolysis; epimerization; Heating; Title compound not separated from byproducts.; |
ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate
L-Tic-OH
Conditions | Yield |
---|---|
With chicken liver acetone; water pH=7.5; |
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
L-Tic-OH
Conditions | Yield |
---|---|
With chicken liver acetone; water for 2h; pH=7.5; |
L-Tic-OH
Conditions | Yield |
---|---|
With chicken liver acetone; water pH=7.5; |
Conditions | Yield |
---|---|
Stage #1: α,α'-dibromo-o-xylene; chiral Ni complex of Schiff base of glycine and BPB With sodium hydroxide In acetonitrile at 20℃; for 0.666667h; Stage #2: In hydrogenchloride; methanol at 50℃; for 0.333333h; Stage #3: In ammonium hydroxide |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 91 percent / dimethylsulfoxide 2: 65 percent / SOCl2 3: BF3*OEt2 / 20 °C 4: 72 percent / H2O / propan-2-ol / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 91 percent / dimethylsulfoxide 2: 82 percent / TFA / CHCl3 / 0.5 h 3: 72 percent / H2O / propan-2-ol / 20 °C View Scheme |
(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one
L-Tic-OH
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 65 percent / SOCl2 2: BF3*OEt2 / 20 °C 3: 72 percent / H2O / propan-2-ol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 82 percent / TFA / CHCl3 / 0.5 h 2: 72 percent / H2O / propan-2-ol / 20 °C View Scheme |
(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-3-chloromethyl-1,3-oxazolidin-5-one
L-Tic-OH
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BF3*OEt2 / 20 °C 2: 72 percent / H2O / propan-2-ol / 20 °C View Scheme |
(+/-)-2-acetyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
L-Tic-OH
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 86 percent / 6 N aq. HCl / 4 h / Heating 2: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 3: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme |
o-Xylylene dichloride
L-Tic-OH
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: NaOMe / 4 h / Heating 2: 6 N aq. HCl / 4 h / Heating 3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 4: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: NaOMe / 4 h / Heating 2: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1 3: 86 percent / 6 N aq. HCl / 4 h / Heating 4: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 5: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme |
dimethyl 2-acetyl-1,2,3,4-tetrahydro-3,3-isoquinolinedicarboxylate
L-Tic-OH
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 6 N aq. HCl / 4 h / Heating 2: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 3: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1 2: 86 percent / 6 N aq. HCl / 4 h / Heating 3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 4: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 75 percent / NaOMe / 4 h / Heating 2: 6 N aq. HCl / 4 h / Heating 3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 4: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: 75 percent / NaOMe / 4 h / Heating 2: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1 3: 86 percent / 6 N aq. HCl / 4 h / Heating 4: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 5: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme |
Phenylalanine
L-Tic-OH
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 69 percent / conc. HCl View Scheme |
Conditions | Yield |
---|---|
In hydrogenchloride; ethanol; water |
formaldehyd
2-methyl-3-phenylpropionic acid
L-Tic-OH
Conditions | Yield |
---|---|
With hydrogenchloride; water Reflux; |
methanol
L-Tic-OH
methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
With thionyl chloride at 0 - 20℃; | 96% |
With sulfuric acid for 12h; Reflux; | 95% |
chloroformic acid ethyl ester
L-Tic-OH
2-carboethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water 1.) 0 deg C to room temperature, 2.) room temperature, 3 h; | 100% |
di-tert-butyl dicarbonate
L-Tic-OH
(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; | 100% |
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; Time; | 100% |
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; Concentration; | 100% |
methanol
L-Tic-OH
(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
With thionyl chloride at 0 - 40℃; for 21h; Inert atmosphere; | 99% |
With thionyl chloride at 0 - 40℃; for 21h; Inert atmosphere; | 99% |
With chloro-trimethyl-silane at 70℃; for 2h; Reflux; |
L-Tic-OH
benzyl chloroformate
(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 16h; | 99% |
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 16.5h; | 99% |
With sodium hydrogencarbonate In water at 20℃; for 1.5h; | 97% |
L-Tic-OH
(S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran for 6h; Reduction; Heating; | 96% |
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Heating; | 86% |
With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran | 78% |
phosgene
L-Tic-OH
(10aS)-10,10a-dihydro[1,3]oxazolo[3,4-b]isoquinoline-1,3,(5H)-dione
Conditions | Yield |
---|---|
In tetrahydrofuran; dichloromethane at -30 - 20℃; | 95% |
L-Tic-OH
(S)-7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at -20℃; for 0.5h; | 93% |
With sulfuric acid; nitric acid at -10℃; for 3.5h; | 90% |
With sulfuric acid; potassium nitrate at 5 - 20℃; |
formaldehyd
L-Tic-OH
Conditions | Yield |
---|---|
With formic acid for 4h; Reflux; | 93% |
formaldehyd
L-Tic-OH
Conditions | Yield |
---|---|
Stage #1: formaldehyd; L-Tic-OH With formic acid In water for 4h; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice; | 93% |
ethanol
L-Tic-OH
ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
Conditions | Yield |
---|---|
With thionyl chloride Reflux; | 91% |
With thionyl chloride | |
With sulfuric acid at 80℃; for 20h; Inert atmosphere; |
trimethylsilyl cyanide
benzaldehyde
L-Tic-OH
2-benzyl-1,2,3,4-tetrahydroisoquinoline-3-carbonitrile
Conditions | Yield |
---|---|
In butan-1-ol at 200℃; for 0.166667h; decarboxylative Strecker reaction; Microwave irradiation; enantioselective reaction; | 91% |
Fmoc-Leu-OH
Fmoc-Pro-OH
N-Fmoc L-Phe
Fmoc-Asn-OH
Fmoc-L-Arg-OH
L-Tic-OH
trifluoroacetic acid
Conditions | Yield |
---|---|
Stage #1: Fmoc-Asn-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 2h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: Fmoc-Leu-OH; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-L-Arg-OH; L-Tic-OH; trifluoroacetic acid Further stages; | 89% |
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
L-Tic-OH
Conditions | Yield |
---|---|
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of iridium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, concn., addn. of Et2O, filtration, washing with Et2O, pentane, drying in vac.; elem. anal.; | 85% |
copper(II) acetate monohydrate
L-Tic-OH
Conditions | Yield |
---|---|
In methanol (Ar); addn. of ligand to a soln. of copper salt in methanol; isolation, washing with methanol, ether, drying in vac.; elem. anal.; | 84% |
Conditions | Yield |
---|---|
With thionyl chloride at 120℃; for 16h; Inert atmosphere; | 84% |
L-Tic-OH
N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
L-alanine acid chloride
quinapril
Conditions | Yield |
---|---|
With benzenesulfonamide; phosphorus pentachloride; triethylamine In n-heptane; dichloromethane; water | 83.9% |
L-Tic-OH
isoquinoline-3-carboxylic acid
Conditions | Yield |
---|---|
With potassium permanganate In N,N-dimethyl-formamide at 0 - 20℃; for 100.5h; Inert atmosphere; | 83% |
With potassium permanganate | 83% |
With potassium permanganate In N,N-dimethyl-formamide at 20℃; for 72h; Cooling with ice; | 62% |
Conditions | Yield |
---|---|
In methanol (Ar); addn. of ligand to a soln. of copper salt in methanol; isolation, washing with methanol, ether, drying in vac.; elem. anal.; | 81% |
N-(tert-butyloxycarbonyl) azide
L-Tic-OH
(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; pH=10; | 80% |
(Z)-9-octadecenoyl chloride
L-Tic-OH
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone at 0 - 20℃; | 78% |
glycolaldehyde dimer
tert-butylisonitrile
L-Tic-OH
Conditions | Yield |
---|---|
In 2,2,2-trifluoroethanol at -40 - 20℃; for 12h; Ugi reaction; | 77% |
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
L-Tic-OH
Conditions | Yield |
---|---|
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of ruthenium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration through celite, concn., addn. to pentane, filtration, washing with pentane, drying in vac.; elem. anal.; | 77% |
trans-di-μ-chloro-dichlorobis(triethylphosphine)diplatinum
L-Tic-OH
Conditions | Yield |
---|---|
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of platinum complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, addn. of pentane, washing withpentane, drying in vac.; elem. anal.; | 77% |
L-Tic-OH
Conditions | Yield |
---|---|
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of palladium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, evapn., addn. of pentane, cooling to -20°C, washing with pentane, drying in vac.; elem. anal.; | 76% |
N-(Benzyloxycarbonyloxy)succinimide
L-Tic-OH
(S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 27h; | 74.7% |
IUPAC Name: (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Synonyms of L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (CAS NO.74163-81-8): 3-Isoquinolinecarboxylicacid, 1,2,3,4-tetrahydro-, (S)- ; (3S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid ; S-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
CAS NO: 74163-81-8
Molecular Formula: C10H11NO2
Molecular Weight: 177.20
Molecular Structure:
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.576
Molar Refractivity: 47.88 cm3
Molar Volume: 144.5 cm3
Surface Tension: 48.2 dyne/cm
Density: 1.225 g/cm3
Flash Point: 178.8 °C
Enthalpy of Vaporization: 65.31 kJ/mol
Boiling Point: 372 °C at 760 mmHg
Vapour Pressure: 3.41E-06 mmHg at 25°C
Melting point: 300 °C
Alpha: -157.4 º (24°C)
Storage temp: Store at 0-5°C
Appearance: white to light yellow crystal powder
Product Categories of L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (CAS NO.74163-81-8): Amino Acids;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;chiral;(intermediate of quinapril);Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;IsoquinolinesPeptide Synthesis;Chiral Building Blocks;Heterocyclic Building Blocks;Others;Unnatural Amino Acid Derivatives;Peptide Synthesis;a-amino
Safety Information about L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (CAS NO.74163-81-8):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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