beta-Narcotine

Base Information

• Chemical Name: beta-Narcotine
• CAS No.: 3860-46-6
• Molecular Formula: C22H23NO7
• Molecular Weight: 413.427
• European Community (EC) Number: 684-374-6
• DSSTox Substance ID: DTXSID70191919
• Nikkaji Number: J38.650B
• Wikidata: Q27165285
• Metabolomics Workbench ID: 123446
• ChEMBL ID: CHEMBL1403892
• Mol file: 3860-46-6.mol

Synonyms:beta-Narcotine;L-beta-Narcotine;3860-46-6;(3R)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R-(R*,R*))-;Noscapine [INN:BAN:JAN];C22-H23-N-O7;NCGC00016388-01;CAS-128-62-1;(-)-beta-narcotine;Spectrum_001069;Spectrum2_000987;Spectrum3_000527;Spectrum4_000456;Spectrum5_001276;Lopac-N-9007;BSPBio_002113;KBioGR_000872;KBioSS_001549;SPBio_001053;SCHEMBL7862895;CHEMBL1403892;CHEBI:93592;KBio2_001549;KBio2_004117;KBio2_006685;KBio3_001613;DTXSID70191919;1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (S-(R*,S*))-;6035-40-1;TNP00034;TNP00110;CCG-36462;AKOS021650200;SDCCGMLS-0066644.P001;NCGC00015757-01;NCGC00015757-02;NCGC00015757-03;NCGC00015757-06;NCGC00016388-03;NCGC00017174-01;NCGC00017174-02;(3R)-3-((5R)-4-methoxy-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxoleno[4,5-g]isoq uinolin-5-yl))-6,7-dimethoxy-3-hydroisobenzofuran-1-one;LS-97535;SBI-0206692.P002;AB00053507_10;BRD-K91301684-003-02-2;Q27165285;(3R)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-isobenzofuran-1-one

Chemical Property of beta-Narcotine

Chemical Property:

• Boiling Point: 565.3°Cat760mmHg
• Flash Point: 295.7°C
• PSA: 75.69000
• Density: 1.332g/cm³
• LogP: 2.81970
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 413.14745207
• Heavy Atom Count: 30
• Complexity: 647

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C(=C2[C@@H]1[C@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3

Technology Process of beta-Narcotine

There total 55 articles about beta-Narcotine 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: 82.0%

(+/-)-α-3-(9-bromo-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-6,7-dimethoxy-1(3H)-isobenzofuranone → (±)-α-noscapine (128-62-1,3860-46-6,6035-40-1,10421-76-8,35933-62-1,35933-63-2,35933-64-3,85280-20-2)

Guidance literature:

With hydrogen; triethylamine; for 30h;

DOI:10.1016/j.tet.2011.05.060

Reference yield: 46.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (+/-)-erythro-1-<1'-(4',5'-dimethoxyphthalidyl)>-8-methoxy-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (36017-64-8) → (±)-α-noscapine (128-62-1,3860-46-6,6035-40-1,10421-76-8,35933-62-1,35933-63-2,35933-64-3,85280-20-2)

Guidance literature:

With formic acid; In water; at 100 ℃; for 0.166667h;

Reference yield: 42.0%

4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide (30936-27-7) + 6,7-dimethoxy-3-(trimethylsilyl)isobenzofuran-1(3H)-one (133932-07-7) → (±)-α-noscapine (128-62-1,3860-46-6,6035-40-1,10421-76-8,35933-62-1,35933-63-2,35933-64-3,85280-20-2)

Guidance literature:

With potassium hydrogen difluoride; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.3987/COM-13-12843

upstream raw materials:

1S,9S β-narcotine

3-methoxy-4,5-methylenedioxybenzaldehyde

(E)-4-methoxy-6-(2-nitrovinyl)benzo[d][1,3]dioxole

β-(3-methoxy-4,5-methylenedioxy)phenylethylamine

Downstream raw materials:

(±)-β-noscapine

4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol

2,3-dimethoxy-6-{[4-methoxy-6-(2-methylamino-ethyl)-benzo[1,3]dioxol-5-yl]-acetyl}-benzoic acid

(3,4-dimethoxy-2-methyl-phenyl)-(4-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-methanone