Dihydrothebainone

Base Information

• Chemical Name: Dihydrothebainone
• CAS No.: 847-86-9
• Molecular Formula: C18H23 N O3
• Molecular Weight: 301.386
• Hs Code.: 2939190000
• European Community (EC) Number: 212-696-5
• NSC Number: 134598,35545
• DSSTox Substance ID: DTXSID901005004
• Wikidata: Q76304859
• ChEMBL ID: CHEMBL1607478
• Mol file: 847-86-9.mol

Synonyms:dihydrothobainone

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Chemical Property of Dihydrothebainone

Chemical Property:

• Vapor Pressure: 1.81E-09mmHg at 25°C
• Melting Point: 150-151 °C(Solv: ethanol (64-17-5))
• Boiling Point: 470.3°C at 760 mmHg
• PKA: 8.55±0.20(Predicted)
• Flash Point: 238.2°C
• PSA: 49.77000
• Density: 1.26g/cm³
• LogP: 2.20590
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 301.16779360
• Heavy Atom Count: 22
• Complexity: 467

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23CC(=O)CCC2C1CC4=C3C(=C(C=C4)OC)O
• Isomeric SMILES: CN1CC[C@]23CC(=O)CC[C@H]2[C@H]1CC4=C3C(=C(C=C4)OC)O
• Uses: Morphinan derivative. Used in the preparation of ABC drug transporter inhibitors.

Technology Process of Dihydrothebainone

There total 67 articles about Dihydrothebainone 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: 100.0%

O-Methyldihydrothebainone (74924-35-9) → (-)-Dihydrothebainon (847-86-9)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 100 ℃; for 10h;

DOI:10.1021/jo00150a017

Reference yield: 99.5%

codeine phosphate (52-28-8) → (-)-Dihydrothebainon (847-86-9) + dihydrocodeine (125-28-0)

Guidance literature:

With sodium hydroxide; hydrogen; platinum; 5% platinum on charcoal; In water; at 25 - 30 ℃; under 517.162 - 2585.81 Torr; pH=7.5;

Reference yield: 98.2%

codeine phosphate (52-28-8) → (-)-Dihydrothebainon (847-86-9) + dihydrocodeine (125-28-0) + Hydrocodone (125-29-1)

Guidance literature:

With hydrogen; platinum; 5% platinum on charcoal; In water; at 25 - 30 ℃; under 517.162 - 2585.81 Torr; pH=4.2;

upstream raw materials:

thebaine

8,14-dihydrothebaine

(+/-)-dihydrocodeinone

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

Downstream raw materials:

1-Brom-4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-on

(-)-tetrahydrodeoxycodeine

1-bromodihydrothebainone

dihydrothebainone-4-phenyl ether

Refernces

• 1、 Moos,Gless,Rapoport. "Codeine analogues. Synthesis of 4a-aryldecahydroisoquinolines containing nitrogen ring functionality and of octahydro-1H-indeno[1,2,3-ef]isoquinolines. A total synthesis of codeine". . p. 227 - 238. Retrieved 1983.
• 2、 -. "MORPHAN AND MORPHINAN ANALOGUES, AND METHODS OF USE". Page/Page column 74. . Retrieved 2014/12/12.
• 3、 Hupp, Christopher D.,Neumeyer, John L.. "Rapid access to morphinones: removal of 4,5-ether bridge with Pd-catalyzed triflate reduction". scheme or table. p. 2359 - 2361. Retrieved 2010/06/13.