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

Base Information

• Chemical Name: (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 118864-75-8
• Molecular Formula: C₁₅H₁₅N
• Molecular Weight: 209.291
• Hs Code.: 2942000000
• European Community (EC) Number: 445-640-5,601-570-9
• UNII: N5NZ4W5RGQ
• DSSTox Substance ID: DTXSID80922796
• Nikkaji Number: J825.518K
• Wikidata: Q72498854
• Mol file: 118864-75-8.mol

Synonyms:118864-75-8;(1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline;(S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline;(S)-1-phenyl-1,2,3,4-tetrahydro-isoquinoline;N5NZ4W5RGQ;(1S)-1,2,3,4-tetrahydro-1-phenylisoquinoline;MFCD08692036;Isoquinoline, 1,2,3,4-tetrahydro-1-phenyl-, (1S)-;Isoquinoline, 1,2,3,4-tetrahydro-1-phenyl-, (S)-;(S)-1,2,3,4-TETRAHYDRO-1-PHENYLISOQUINOLINE;(1S)-1-Phenyl-1,2,3,4-tetrahydro-isopquinoline;UNII-N5NZ4W5RGQ;SCHEMBL325083;DTXSID80922796;AMY37044;CS-B0308;AKOS015889792;AKOS016023743;CS-O-31497;AS-15681;P2216;1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline;1alpha-Phenyl-1,2,3,4-tetrahydroisoquinoline;EN300-224815;(1S)-1-Phenyl-1,2,3,4 -tetrahydroisoquinoline;Q-101005;Z1509140606

Chemical Property of (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 9.87E-05mmHg at 25°C
• Melting Point: 80-82 °C
• Refractive Index: 1.589
• Boiling Point: 338.4 °C at 760 mmHg
• PKA: 8.91±0.40(Predicted)
• Flash Point: 167 °C
• PSA: 12.03000
• Density: 1.065 g/cm³
• LogP: 3.25050
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 209.120449483
• Heavy Atom Count: 16
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C2=CC=CC=C21)C3=CC=CC=C3
• Isomeric SMILES: C1CN[C@H](C2=CC=CC=C21)C3=CC=CC=C3
• General Description: (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline is a chiral intermediate of pharmaceutical significance, particularly in the synthesis of solifenacin, a muscarinic acetylcholine receptor antagonist used as a urinary antispasmodic. Its enantioselective preparation has been achieved via asymmetric hydrogenation of 1-phenyl-3,4-dihydroisoquinoline using iridium-based catalysts, yielding high enantiomeric excess (>98% ee) and purity. Additionally, enzymatic approaches using imine reductases (IREDs) have been developed to synthesize such 1-aryl-substituted tetrahydroisoquinolines with high stereoselectivity, overcoming steric challenges posed by aryl substituents. (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline’s structural motif is also leveraged in other bioactive molecules, highlighting its versatility in medicinal chemistry.

Technology Process of (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

There total 76 articles about (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.9%

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline tartarate (869884-00-4) → (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8)

Guidance literature:

With sodium hydroxide; In water; for 1.5h; pH=8.5;

Reference yield: 95.0%

(S)-2-[(R)-tert-butylsulfinyl]-1-phenyl-1,2,3,4-tetrahydroisoquinoline → (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; at 0 - 20 ℃; for 1h;

DOI:10.1055/s-0034-1378515

Reference yield: 90.0%

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → 1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8)

Guidance literature:

With hydrogenchloride; borane-ammonia complex; In aq. phosphate buffer; at 37 ℃; pH=7.8;

DOI:10.1021/ja4051235

upstream raw materials:

(1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

(S)-(-)-benzyl 1-phenyl-1,2-dihydroisoquinoline-2-carboxylate

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

(1S,5R)-5,8,8-trimethyl-1-[(1S)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one

Downstream raw materials:

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

(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester succinate

(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate

solifenacin succinate