(S)-Laudanine

Base Information

• Chemical Name: (S)-Laudanine
• CAS No.: 3122-95-0
• Molecular Formula: C20H25NO4
• Molecular Weight: 343.423
• UNII: 347215J9V9
• DSSTox Substance ID: DTXSID10356308
• Nikkaji Number: J356.772I
• Wikidata: Q27145751
• Metabolomics Workbench ID: 129520
• ChEMBL ID: CHEMBL251625
• Mol file: 3122-95-0.mol

Synonyms:(S)-Laudanine;L-(+)-Laudanidine;(+)-Laudanidine;3122-95-0;Laudanine, (+)-;1alphaH-Laudanidine;(+)-laudanine;UNII-347215J9V9;5-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-methoxyphenol;347215J9V9;CHEBI:76101;Phenol, 2-methoxy-5-(((1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-;5-[((1S)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol;5-{[(1S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-methoxyphenol;1.ALPHA.H-LAUDANIDINE;CHEMBL251625;SCHEMBL15696580;DTXSID10356308;Phenol, 2-methoxy-5-[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl]-, (S)-;C20712;Q27145751;2-Methoxy-5-[[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolin)-1alpha-yl]methyl]phenol

Chemical Property of (S)-Laudanine

Chemical Property:

• PSA: 51.16000
• LogP: 3.12760
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 343.17835828
• Heavy Atom Count: 25
• Complexity: 421

Purity/Quality:

97% ^*data from raw suppliers

(S)-Laudanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)OC)OC
• Uses: An alkaloid from Xylopia championii as antioxidant and antifungal agent.

Technology Process of (S)-Laudanine

There total 11 articles about (S)-Laudanine 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: 98.0%

(S)-(-)-1-[4-methoxy-3-(triisopropylsilanyloxy)benzyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1344118-38-2) → (S)-(+)-1-(3-hydroxy-4-methoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (3122-95-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo201871c

Reference yield: 70.0%

(+)-O,O,O-Trimethylvateamine (87183-78-6) → (S)-(+)-1-(3-hydroxy-4-methoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (3122-95-0) + (S)-laudanosine (2688-77-9,20412-65-1)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; 1) -78 degC, 0.5-2 h, 2) warm to room temp.;

DOI:10.1021/jo00170a016

Reference yield: 10.0%

iodomethane-d3 (865-50-9) + (+)-reticuline N-oxide → [3',7-D6]laudanosine (1242242-84-7) + [7-D3]laudanine (3122-95-0)

Guidance literature:

iodomethane-d3; (+)-reticuline N-oxide; With potassium hydroxide; In tetrahydrofuran; ethanol; at 20 ℃;

With sodium hydrogensulfite; In ethanol; water; for 5h;

DOI:10.1016/j.phytochem.2010.04.022

upstream raw materials:

(S)-1-(3-benzoyloxy-4-methoxy-benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

(+)-O,O,O-Trimethylvateamine

(+)-Vateamine

4-methoxy-3-(triisopropylsilanyloxy)benzyl bromide

Downstream raw materials:

(+)-O-methylthalibrine

Refernces

• 1、 Han, Xu,Lamsh?ft, Marc,Grobe, Nadja,Ren, Xuan,Fist, Anthony J.,Kutchan, Toni M.,Spiteller, Michael,Zenk, Meinhart H.. "The biosynthesis of papaverine proceeds via (S)-reticuline". experimental part. p. 1305 - 1312. Retrieved 2011/04/22.