Thebainone

Base Information

• Chemical Name: Thebainone
• CAS No.: 467-98-1
• Molecular Formula: C18H21 N O3
• Molecular Weight: 299.37
• UNII: 410TP47E6I
• DSSTox Substance ID: DTXSID60878328,DTXSID30871649
• Wikidata: Q27258369
• Mol file: 467-98-1.mol

Synonyms:Thebainone;Thebainone A;467-98-1;UNII-410TP47E6I;410TP47E6I;7,8-Didehydro-4-hydroxy-3-methoxy-17-methylmorphinan-6-one;thebainone-A;(1S,9R,10R)-3-hydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one;(-)-Thebainone A;THEBAINONE [MI];SCHEMBL8819854;DTXSID30871649;DTXSID60878328;Q27258369;Morphinan-6-one, 7,8-didehydro-4-hydroxy-3-methoxy-17-methyl-;-rel-(4aS,10R,10aR)-5-Hydroxy-6-methoxy-11-methyl-10,10a-dihydro-4H-10,4a-(epiminoethano)phenanthren-3(9H)-one;141901-28-2

Chemical Property of Thebainone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 142-144°C
• Refractive Index: 1.5740 (estimate)
• Boiling Point: 475.4°Cat760mmHg
• Flash Point: 241.3°C
• PSA: 49.77000
• Density: 1.29g/cm³
• LogP: 1.98190
• Storage Temp.: Controlled Substance, -20°C Freezer
• Water Solubility.: 4g/L(20 oC)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 299.15214353
• Heavy Atom Count: 22
• Complexity: 505

Purity/Quality:

98% ^*data from raw suppliers

THEBAINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23CC(=O)C=CC2C1CC4=C3C(=C(C=C4)OC)O
• Isomeric SMILES: CN1CC[C@]23CC(=O)C=C[C@H]2[C@H]1CC4=C3C(=C(C=C4)OC)O
• Uses: A new metabolite of Thebaine Controlled substance.

Technology Process of Thebainone

There total 29 articles about Thebainone 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: 8.0%

3,6-dimethoxy-17-methyl-morphina-5,8-dien-4-ol (6878-93-9) → 4-hydroxy-3-methoxy-17-methyl-14α-morphin-7-en-6-one (596-59-8) + 7,8-didehydro-4-hydroxy-3-methoxy-17-methyl-morphinan-6-one (467-98-1)

Guidance literature:

With hydrogenchloride; at 95 ℃; for 0.583333h;

DOI:10.1080/00397919808005110

Reference yield:

C20H25NO4 → (±)-thebainone A (467-98-1,596-59-8,141901-27-1,141901-28-2)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00905

Reference yield:

β-thebainone-A (467-98-1,596-59-8,141901-27-1,141901-28-2) → (±)-thebainone A (467-98-1,596-59-8,141901-27-1,141901-28-2)

Guidance literature:

With acetic acid; at 100 ℃; for 1h;

DOI:10.1021/ja00041a008

upstream raw materials:

3,6-dimethoxy-17-methyl-morphina-5,8-dien-4-ol

β-thebainone-A

ent-4-hydroxy-3-methoxy-17-methyl-morphin-7-en-6-one

trans-morphinan

Downstream raw materials:

(-)-Dihydrothebainon

dihydrothebainone-4-phenyl ether

dihydrothebainone-4-phenyl ether ethylene glycol ketal

3-methoxy-17-methylmorphinan-6-one

Refernces

• 1、 Hahn, Christian,Hennig, André,J?ger, Anne,Küttler, Thomas,Metz, Peter,Wang, Yuzhou. "Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition". . . Retrieved 2020/04/21.
• 2、 Van Gurp,Lie,Mense,Maat. "Synthesis of 7,8-didehydro-3,4-dimethoxy-17-methylmorphinan-6-one and the regioselective reduction of the keto function". . p. 325 - 329. Retrieved 2007/10/02.