R-Tetrahydropapaverine

Base Information

• Chemical Name: R-Tetrahydropapaverine
• CAS No.: 54417-53-7
• Molecular Formula: C20H25NO4
• Molecular Weight: 379.884
• Hs Code.: 2933499090
• European Community (EC) Number: 415-110-8,680-305-9
• DSSTox Substance ID: DTXSID20866423
• Nikkaji Number: J430.264H
• Wikidata: Q27464875
• Mol file: 54417-53-7.mol

Synonyms:R-Tetrahydropapaverine;50896-90-7;54417-53-7;(R)-(+)-Tetrahydropapaverine;R-tetrahydropapaverine HCl;(R)-1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(1~{r})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline;R-(+)-Tetrahydropapaverin;(R)-norlaudanosine;(1r)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;SCHEMBL6398843;DTXSID20866423;CHEBI:136735;MFCD09750421;AKOS022172001;AS-11440;PD132150;CS-0200220;Q27464875;(r)-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline;R9T

Chemical Property of R-Tetrahydropapaverine

Chemical Property:

• Vapor Pressure: 3.23E-09mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 475.8 °C at 760 mmHg
• Flash Point: 202.7 °C
• PSA: 48.95000
• Density: 1.12 g/cm3
• LogP: 4.28130
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 343.17835828
• Heavy Atom Count: 25
• Complexity: 407

Purity/Quality:

99%min ^*data from raw suppliers

(R)-(-)-NorlaudanosineHCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-52/53
• Safety Statements: 22-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC2C3=CC(=C(C=C3CCN2)OC)OC)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)C[C@@H]2C3=CC(=C(C=C3CCN2)OC)OC)OC

Technology Process of R-Tetrahydropapaverine

There total 4 articles about R-Tetrahydropapaverine 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: 83.25%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5,66820-84-6) → (R)-tetrahydropapaverine hydrochloride (54417-53-7,66820-84-6)

Guidance literature:

With N-acetyl-D-leucine; (R)-N-acetylphenylalanin; In water; toluene; acetonitrile; at 4 - 70 ℃; for 24.92h; Reagent/catalyst;

Reference yield:

(-) N-norlaudanosine (50896-90-7) → (R)-tetrahydropapaverine hydrochloride (54417-53-7,66820-84-6)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 20 ℃; for 1h;

Reference yield:

C25H26N2O6S + methyl iodide (74-88-4) → (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride (54417-52-6,66820-84-6) + (R)-tetrahydropapaverine hydrochloride (54417-53-7,66820-84-6)

Guidance literature:

C₂₅H₂₆N₂O₆S; methyl iodide; With potassium carbonate; In acetonitrile; at 80 ℃; for 18h;

With hydrogenchloride; In ethanol; dichloromethane; water; at 20 ℃; for 24h; Overall yield = 78 %; Overall yield = 48 mg;

DOI:10.1021/acs.joc.5b00509

upstream raw materials:

3,4-dihydropapaverine

(-) N-norlaudanosine

methyl iodide

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride

Downstream raw materials:

(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butylaminocarbonylethyl-isoquinoline oxalate

(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethyl-isoquinoline oxalate

(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methoxycarbonylethyl-isoquinoline oxalate

(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-benzyloxycarbonylethyl-isoquinoline oxalate

Refernces

• 1、 Ruiz-Olalla, Andrea,Würdemann, Martien A.,Wanner, Martin J.,Ingemann, Steen,Van Maarseveen, Jan H.,Hiemstra, Henk. "Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids". . p. 5125 - 5132. Retrieved 2015/05/27.
• 2、 -. "PROCESS FOR THE RESOLUTION OF ISOQUINOLINE DERIVATIVES". Page/Page column 9-10. . Retrieved 2009/10/21.