Dihydrothebaine

Base Information

• Chemical Name: Dihydrothebaine
• CAS No.: 561-25-1
• Deprecated CAS: 1385-04-2,57281-79-5
• Molecular Formula: C19H23NO3
• Molecular Weight: 313.397
• European Community (EC) Number: 209-216-1
• UNII: 3F3XDX43PO
• DSSTox Substance ID: DTXSID40204641
• Nikkaji Number: J6.493I
• Wikidata: Q27257142
• Mol file: 561-25-1.mol

Synonyms:Dihydrothebaine;8,14-Dihydrothebaine;Thebaine, dihydro-;delta(sup 6)-Dihydrothebaine;EINECS 209-216-1;561-25-1;UNII-3F3XDX43PO;3F3XDX43PO;(5alpha)-6,7-Didehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan;4,5alpha-Epoxy-3,6-dimethoxy-17-methyl-6-morphinen;(5R,9R,13S,14R)-4,5-Epoxy-3,6-dimethoxy-N-methyl-6-morphinen;Morphinan, 6,7-didehydro-4,5-alpha-epoxy-3,6-dimethoxy-17-methyl-;(5R,9R,13S,14R)-4,5-Epoxy-3,6-dimethoxy-N-methyl-6-morphinen [IUPAC];Morphinan, 6,7-didehydro-4,5-epoxy-3,6-dimethoxy-17-methyl- (5-alpha,14-xi)-;8,14 dihydrothebaine;8,14-dihydro-thebaine;DIHYDROTHEBAINE [MI];SCHEMBL553979;.DELTA.6-DIHYDROTHEBAINE;DTXSID40204641;XJZOLKDBHJPTAT-ATNYCFDYSA-N;THEBAINE, 8,14-DIHYDRO-;LS-149302;Q27257142;(5-alpha)-6,7-Didehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan;HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY J [EP IMPURITY];MORPHINAN, 6,7-DIDEHYDRO-4,5-EPOXY-3,6-DIMETHOXY-17-METHYL-, (5.ALPHA.)-;MORPHINAN, 6,7-DIDEHYDRO-4,5.ALPHA.-EPOXY-3,6-DIMETHOXY-17-METHYL-

Chemical Property of Dihydrothebaine

Chemical Property:

• Melting Point: 162-163°
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 453.19°C (rough estimate)
• Flash Point: 135.4oC
• PSA: 30.93000
• Density: 1.1501 (rough estimate)
• LogP: 2.44230
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 535

Purity/Quality:

99% ^*data from raw suppliers

8,14-DIHYDROTHEBAINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=CC4)OC
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3C(=CC4)OC

Technology Process of Dihydrothebaine

There total 10 articles about Dihydrothebaine 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: 96.0%

thebaine (115-37-7) → 8,14-dihydrothebaine (561-25-1)

Guidance literature:

With ethanolamine; toluene-4-sulfonic acid hydrazide; In water; at 110 - 114 ℃; for 2.16667h; Reagent/catalyst; Solvent;

Reference yield: 20.0%

codeine-6-methyl ether (2859-16-7) → 8,14-dihydrothebaine (561-25-1)

Guidance literature:

With RhCl(PPh₃)3; In ethanol; Heating;

DOI:10.1016/j.tetlet.2007.04.051

Reference yield:

dimethyl sulfate (77-78-1) + Hydrocodone (125-29-1) → 8,14-dihydrothebaine (561-25-1)

Guidance literature:

With sodium methylate; tert-butyl alcohol;

DOI:10.1021/jo01109a606

upstream raw materials:

thebaine

dimethyl sulfate

Hydrocodone

methanol

Downstream raw materials:

4-hydroxy-3-methoxy-7ξ,17-dimethyl-morphinan-6-one

4-hydroxy-3-methoxy-5ξ,17-dimethyl-morphinan-6-one

(-)-Dihydrothebainon

7ξ-ethyl-4-hydroxy-3-methoxy-17-methyl-morphinan-6-one

Refernces

• 1、 Pieber, Bartholom?us,Cox, D. Phillip,Kappe, C. Oliver. "Selective Olefin Reduction in Thebaine Using Hydrazine Hydrate and O2 under Intensified Continuous Flow Conditions". . p. 376 - 385. Retrieved 2016/03/04.
• 2、 -. "PROCESSES FOR MAKING HYDROCODONE, HYDROMORPHONE AND THEIR DERIVATIVES". Page/Page column 19. . Retrieved 2015/09/28.