(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

• ChemBase ID: 175672
• Molecular Formular: C20H25NO4
• Molecular Mass: 343.4168
• Monoisotopic Mass: 343.17835829
• SMILES: c1(c(cc2c(c1)[C@@H](NCC2)Cc1cc(c(cc1)OC)OC)OC)OC
• Canonical SMILES: COc1cc(ccc1OC)C[C@@H]1NCCc2c1cc(OC)c(c2)OC
• InChI: InChI=1S/C20H25NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-6,10-12,16,21H,7-9H2,1-4H3/t16-/m0/s1
• InChIKey: YXWQTVWJNHKSCC-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• IUPAC Traditional name: (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (-)-N-Norlaudanosine; (-)-Norlaudanosine; (-)-Tetrahydropapaverine; (S)-(-)-Tetrahydropapaverine; (S)-Norlaudanosine; L-(-)-Tetrahydropapaverine; S-(-)-N-Norlaudanosine; Tetrahydropapaverine; (S)-Nor Laudanosine; (1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline; 2-Demethyllaudanosine; (-)-1,2,3,4-Tetrahydropapaverine

Database IDs

• CAS Number: 4747-98-2
• PubChem SID: 164231582
• PubChem CID: 639354

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.11081835
• LogD (pH = 7.4): 1.1754836
• Log P: 3.0136995
• Molar Refractivity: 97.5062 cm^3
• Polarizability: 37.99663 Å^3
• Polar Surface Area: 48.95 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N710050

Used in the enantioselective synthesis of (+)-(S)-Laudanosine (L178525) and (-)-(S)-Xylopinine.

REFERENCES

• Schmutz, J., et al.: Helv. Chim. Acta, 42, 335 (1959)
• Stenlake, J.B., et al.: Eur. J. Med. Chem., 27, 463(1959)