[(4R,4aS,7aR,12bS)-9-methoxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate

Base Information

• Chemical Name: [(4R,4aS,7aR,12bS)-9-methoxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate
• CAS No.: 70509-92-1
• Molecular Formula: C20H23NO5
• Molecular Weight: 357.406
• Nikkaji Number: J1.507.282B
• Mol file: 70509-92-1.mol

Synonyms:SCHEMBL25931598

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Chemical Property of [(4R,4aS,7aR,12bS)-9-methoxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate

Chemical Property:

• Melting Point: 214-215 °C
• Boiling Point: 500.2±50.0 °C(Predicted)
• PKA: 7.01±0.40(Predicted)
• PSA: 65.07000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 1.66100
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 357.15762283
• Heavy Atom Count: 26
• Complexity: 652

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC12CCC(=O)C3C14CCN(C2CC5=C4C(=C(C=C5)OC)O3)C
• Isomeric SMILES: CC(=O)O[C@@]12CCC(=O)[C@H]3[C@@]14CCN([C@@H]2CC5=C4C(=C(C=C5)OC)O3)C

Technology Process of [(4R,4aS,7aR,12bS)-9-methoxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate

There total 6 articles about [(4R,4aS,7aR,12bS)-9-methoxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] acetate 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: 98.0%

acetic anhydride (108-24-7) + Oxycodone (76-42-6) → 14-acetoxy-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one (70509-92-1)

Guidance literature:

at 100 ℃; for 1h;

DOI:10.1002/recl.19831020303

Reference yield:

thebaine (115-37-7) → 14-acetoxy-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one (70509-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: dihydrogen peroxide / formic acid

2: palladium on carbon; hydrogen

With palladium on carbon; hydrogen; dihydrogen peroxide; In formic acid;

DOI:10.1016/j.saa.2011.03.038

Reference yield:

14-hydroxycodeinone (508-54-3) → 14-acetoxy-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one (70509-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium on carbon; hydrogen

With palladium on carbon; hydrogen;

DOI:10.1016/j.saa.2011.03.038

upstream raw materials:

acetic anhydride

Oxycodone

14-hydroxycodeinone

thebaine

Downstream raw materials:

Naltrexone

naloxone hydrochloride

14-acetoxy-4,5α-epoxy-3-methoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinane

4,5α-epoxy-3-methoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinan-14-ol

Refernces

• 1、 Cantillo, David,Glotz, Gabriel,Kappe, C. Oliver. "Electrochemical N-Demethylation of 14-Hydroxy Morphinans: Sustainable Access to Opioid Antagonists". supporting information. p. 6891 - 6896. Retrieved 2020/09/15.
• 2、 Tavakol, Hossein,Esfandyari, Maryam,Taheri, Salman,Heydari, Akbar. "Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: A combined experimental and theoretical study". scheme or table. p. 574 - 582. Retrieved 2011/07/31.