(1~{s})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline

Base Information

• Chemical Name: (1~{s})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline
• CAS No.: 4747-98-2
• Molecular Formula: C20H25 N O4
• Molecular Weight: 343.423
• DSSTox Substance ID: DTXSID50348641
• Nikkaji Number: J390.169F
• Wikidata: Q27465279
• Mol file: 4747-98-2.mol

Synonyms:4747-98-2;(S)-(-)-Tetrahydropapaverine;(1~{s})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline;(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(S)-tetrahydropapaverine;(1S)-1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;(S)-Nor Laudanosine;Norlaudanosins;S9T;(?)-Norlaudanosine;S-Tetrahydropapaverine;SCHEMBL251076;DTXSID50348641;AKOS015895933;AT38019;C21631;Q27465279;(1s)-1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoQUINOLINE;(S)-1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE

Chemical Property of (1~{s})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline

Chemical Property:

• Melting Point: 80-82 °C
• Boiling Point: 475.8±45.0 °C(Predicted)
• PKA: 8.66±0.40(Predicted)
• PSA: 48.95000
• Density: 1.120
• LogP: 3.47930
• Solubility.: Chloroform, DMSO, Methanol
• 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:

90.0%Min ^*data from raw suppliers

(S)-NorLaudanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Uses: (S)-(-)-Tetrahydropapaverine can be used in the enantioselective. Used in the enantioselective synthesis of (+)-(S)-Laudanosine (L178525) and (-)-(S)-Xylopinine.

Technology Process of (1~{s})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline

There total 58 articles about (1~{s})-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-Dimethoxy-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: 85.0%

(1S,1'R)-1-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-phenylethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline → S-(-)-Norlaudanosine (4747-98-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1248/cpb.39.1126

Reference yield: 83.0%

(S)-2-[(S)-1-(2-Chloro-phenyl)-ethyl]-1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline (121443-94-5) → S-(-)-Norlaudanosine (4747-98-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1021/ja00195a044

Reference yield: 83.0%

3,4-dihydropapaverine (6957-27-3) → S-(-)-Norlaudanosine (4747-98-2)

Guidance literature:

With aluminum oxide; sodium tris[(S)-N,N-phthaloylleucine]borohydride;

DOI:10.1021/jo990267k

upstream raw materials:

Tetrahydropapaverine

4-bromomethyl-1,2-dimethoxybenzene

6,7-dimethoxy-1,2,3,4-tetrahydro-2-[(1-tert-butoxy-3-methyl)-2-butyliminomethyl]isoquinoline

2-Benzoyl-1-<(3,4-dimethoxyphenyl)methyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

N,N'-4,7-dioxa-3,8-dioxodecylene-1,10-diyl-bis-(S)-(+)-tetrahydropapaverine

(S)-laudanosine

(S)-(-)-norcoralydine

(+)-N,N'-4,11-dimethyl-4,11-diaza-3,12-dioxotetramethylene-1,14-diyl-bis(S)-tertahydropapaverine

Refernces

• 1、 Yang, Lu,Zhu, Jinmei,Sun, Chenghai,Deng, Zixin,Qu, Xudong. "Biosynthesis of plant tetrahydroisoquinoline alkaloids through an imine reductase route". . p. 364 - 371. Retrieved 2020/01/21.
• 2、 Zhu, Ruiheng,Xu, Zhangli,Ding, Wei,Liu, Shiling,Shi, Xiaoxin,Lu, Xia. "Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method". . p. 1039 - 1048. Retrieved 2016/02/18.