(-)-Metazocine

Base Information

• Chemical Name: (-)-Metazocine
• CAS No.: 21286-60-2
• Deprecated CAS: 24989-43-3
• Molecular Formula: C₁₅H₂₁NO
• Molecular Weight: 231.338
• European Community (EC) Number: 223-097-3
• UNII: 43F5BF98QO
• DSSTox Substance ID: DTXSID20872483
• Nikkaji Number: J500.427F
• Wikipedia: Metazocine
• Wikidata: Q27890225
• NCI Thesaurus Code: C96731
• Metabolomics Workbench ID: 69755

Synonyms:1,2,3,4,5,6-hexahydro-3,6,11-trimethyl-2,6-methano-3-benzazocin-8-ol;metazocine

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Chemical Property of (-)-Metazocine

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 231.162314293
• Heavy Atom Count: 17
• Complexity: 305

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C2CC3=C(C1(CCN2C)C)C=C(C=C3)O
• Isomeric SMILES: C[C@H]1[C@H]2CC3=C([C@@]1(CCN2C)C)C=C(C=C3)O

Technology Process of (-)-Metazocine

There total 18 articles about (-)-Metazocine 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: 95.0%

O-methyl metazocine (64023-75-2) → (-)-Metazocine (21286-60-2,36402-80-9,75257-89-5,1509-00-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja0360539

Reference yield:

→ 8-Hydroxy-2,6-methano-3,6α,11α-trimethyl-1,2,3,4,5,6-hexahydro-3-benzazocin (3734-52-9,21286-57-7,21286-60-2,25144-79-0,25145-09-9,58640-79-2,64023-94-5,67009-58-9,69831-04-5,36402-80-9,75257-89-5,1509-00-8)

Guidance literature:

2-(4-Hydroxy-benzyl)-1,3,4-trimethyl-1,2,5,6-tetrahydro-pyridin*HCl, AlBr3 (Hauptprod. neben 17percent β-Isomeres);

DOI:10.1021/jo01044a522

Reference yield:

→ (R)-3,6,11-Trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol (3734-52-9,21286-57-7,21286-60-2,25144-79-0,25145-09-9,58640-79-2,64023-94-5,67009-58-9,69831-04-5,36402-80-9,75257-89-5,1509-00-8)

Guidance literature:

β-2,5,9-Trimethyl-2'-amino-6,7-benzomorphan, NaNO2, wss.H2SO4;

upstream raw materials:

(+/-)-3,6,11syn-trimethyl-8-nitro-1,2,3,4,5,6-hexahydro-2,6-methano-benz[d]azocine; hydrochloride

4-methoxybenzylmagnesium chloride

1,3,4-trimethylpyridinium iodide

formaldehyd

Downstream raw materials:

(+)-6,11syn-dimethyl-3-phenethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benz[d]azocin-8-ol

Thiobenzoic acid S-((2R,6R,11R)-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl) ester

Thiobenzoic acid S-((2R,6R,11R)-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl) ester

Thiobenzoic acid S-((6R,11R)-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl) ester