Norreticuline

Base Information

• Chemical Name: Norreticuline
• CAS No.: 13168-51-9
• Molecular Formula: C18H21 N O4
• Molecular Weight: 315.369
• Hs Code.: 2933499090
• Nikkaji Number: J306.166C
• Wikidata: Q27104576
• ChEMBL ID: CHEMBL155707
• Mol file: 13168-51-9.mol

Synonyms:norreticuline;norreticuline, (R)-isomer;norreticuline, (S)-isomer;norreticuline, hydrochloride, (S)-isomer

Chemical Property of Norreticuline

Chemical Property:

• Vapor Pressure: 2.06E-11mmHg at 25°C
• Boiling Point: 519.5°C at 760 mmHg
• Flash Point: 268°C
• PSA: 71.81000
• Density: 1.234g/cm³
• LogP: 2.44350
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 315.14705815
• Heavy Atom Count: 23
• Complexity: 380

Purity/Quality:

99% ^*data from raw 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)O)O
• Uses: Reticuline (R188500) analog. (S)-Norreticuline is the precursor for the biosynthesis of Erythrina alkaloids. (S)-Norreticuline and (S)-reticuline stimulated the proliferation of cultured cells from murine hair.

Technology Process of Norreticuline

There total 26 articles about Norreticuline 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%

1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline (1108621-45-9) → N-benzoyl-norreticuline (13168-51-9)

Guidance literature:

With boron trichloride; In dichloromethane; at -10 - 20 ℃;

DOI:10.1021/jo4023149

Reference yield: 86.0%

N-benzyl-(N-nor)-reticuline (169834-50-8) → N-benzoyl-norreticuline (13168-51-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 1h;

DOI:10.1002/hlca.19810640310

Reference yield:

Benzoic acid (R)-((S)-2-benzoyl-7-benzyloxy-6-methoxy-1,2-dihydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester (135574-24-2) → N-benzoyl-norreticuline (13168-51-9) + Benzoic acid (R)-((S)-2-benzoyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-(3-hydroxy-4-methoxy-phenyl)-methyl ester (135574-69-5)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In isopropyl alcohol; at 70 ℃; for 18h; under 64600 Torr;

DOI:10.1016/S0040-4039(00)74327-9

upstream raw materials:

(-)-Norreticuline

Benzoic acid (R)-((S)-2-benzoyl-7-benzyloxy-6-methoxy-1,2-dihydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester

N-benzyl-(N-nor)-reticuline

4',6-O,O-dimethylpapaveroline

Downstream raw materials:

6'-Chloro-N-norreticuline

(+/-)-6'-Bromo-N-norreticuline

1-(3-Hydroxy-4-methoxybenzyl)-7-hydroxy-6-methoxy-3,4-dihydroisoquinoline N-oxide

(+/-)-Tetrahydropapaveroline hydrobromide

Refernces

• 1、 Dion, Isabelle,Vincent-Rocan, Jean-Francois,Zhang, Lei,Cebrowski, Pamela H.,Lebrun, Marie-Eve,Pfeiffer, Jennifer Y.,Bedard, Anne-Catherine,Beauchemin, Andre M.. "Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products". . p. 12735 - 12749. Retrieved 2014/01/17.
• 2、 -. "PHELLODENDRINE ANALOGS AND ALLERGY TYPE IV SUPPRESSOR CONTAINING THE SAME AS ACTIVE INGREDIENT". . . Retrieved 2008/06/13.