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

Base Information

• Chemical Name: (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 180272-45-1
• Molecular Formula: C15H15N
• Molecular Weight: 209.291
• European Community (EC) Number: 813-246-6
• DSSTox Substance ID: DTXSID40362553
• Nikkaji Number: J825.517B
• Wikidata: Q72498848
• Mol file: 180272-45-1.mol

Synonyms:180272-45-1;(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline;(R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline;(R)-1-Phenyl-1,2,3,4-tetrahydro-isoquinoline;Isoquinoline, 1,2,3,4-tetrahydro-1-phenyl-, (1R)-;SCHEMBL1668148;DTXSID40362553;CS-M0032;MFCD11858641;AKOS016843427;AC-4740;DS-16690;P2215;1beta-Phenyl-1,2,3,4-tetrahydroisoquinoline;EN300-224816;Z1509142487

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

Chemical Property:

• Melting Point: 78-79℃
• Boiling Point: 338.4 °C at 760 mmHg
• Flash Point: 166.9 °C
• PSA: 12.03000
• Density: 1.065 g/cm³
• LogP: 3.25050
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Sparingly), DMSO (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

(R)-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: (R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline is the counterpart to (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline, the latter enantiomer being a key intermediate in the preparation of Solifenacin (S676700), an antimuscarinic agent. Since (R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline is produced as a by-product, it has been suggested that it should be recycled in order to obtain the S enantiomer on a larger scale. (R)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline is also used as a reagent to prepare quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives, compounds that act as muscarinic receptor antagonists.

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

There total 51 articles about (1R)-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: 99.0%

(R)-(+)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (220936-57-2) → (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180272-45-1)

Guidance literature:

With samarium diiodide; water; triethylamine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol301281s

Reference yield: 93.0%

1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8) → (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180272-45-1)

Guidance literature:

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;

With hydrogen; In 1,2-dichloro-ethane; at 30 ℃; for 24h; under 25858.1 Torr; enantioselective reaction;

DOI:10.1021/jacs.5b06659

Reference yield: 82.0%

(1R)-N-(8-menthyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (321670-05-7) → (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180272-45-1)

Guidance literature:

(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;

With potassium hydroxide; In tetrahydrofuran; Further stages.;

DOI:10.1021/jo001397s

upstream raw materials:

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

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

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

1-phenyl-3,4-dihydroisoquinoline

Downstream raw materials:

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

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

solifenacin

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

Refernces

• 1、 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.
• 2、 Wu, Shuke,Zhou, Yi,Rebelein, Johannes G.,Kuhn, Miriam,Mallin, Hendrik,Zhao, Jingming,Igareta, Nico V.,Ward, Thomas R.. "Breaking Symmetry: Engineering Single-Chain Dimeric Streptavidin as Host for Artificial Metalloenzymes". supporting information. p. 15869 - 15878. Retrieved 2019/10/11.