(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
• Uses: Labelled Solifenacin intermediate Solifenacin (S676700) intermediate.

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:

5-<2-(1-phenyl)tetrahydroisoquinolyl>methylene-2,2-dimethyl-1,3-dioxane-4,6-dione

(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

Refernces

• 1、 Babu, R. Anji,Reddy, N. Siva Senkar,Reddy, B. Jagan Mohan,Reddy, B. V. Subba. "Stereoselective Total Syntheses of Solifenacin and N -Acetyl-1-(4-chloro-phenyl)-6,7-dimethoxytetrahydroisoquinoline". . p. 2794 - 2798. Retrieved 2014.
• 2、 Hestericová, Martina. "Directed evolution of artificial metalloenzymes: Genetic optimization of the catalytic activity". . p. 189 - 192. Retrieved 2018.
• 3、 Krishna Rao,Surendra Babu,Basaveswara Rao,Keshavi,Sundara Rao,Eswara Prasad,Murthy. "Synthesis and characterization of S(-)1-phenyl-1,2,3,4-tetrahydro isoquinoline acetamide analogues". . p. 1035 - 1038. Retrieved 2017.
• 4、 Ludwig, Matthias,Beer, Herbert,Lotter, Hermann,Wanner, Klaus Th.. "The absolute configuration of (1S)-(+)- and (1R)-(-)1-phenyl-1,2,3,4-tetrahydroisoquinoline. A revision of the literature assignment". . p. 2693 - 2695. Retrieved 1997.
• 5、 Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin. "Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity". supporting information. p. 6283 - 6287. Retrieved 2020/09/02.
• 6、 -. "Synthesis method of (S)-1-phenyl-1, 2, 3, 4-tetrahydroisoquinoline". Paragraph 0068; 0073-0075; 0080-0082; 0087-0089; 0094-0096. . Retrieved 2021/01/15.