1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone

Base Information

• Chemical Name: 1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone
• CAS No.: 16196-82-0
• Molecular Formula: C23H29 N O4
• Molecular Weight: 383.488
• European Community (EC) Number: 240-326-2
• DSSTox Substance ID: DTXSID40936617
• Nikkaji Number: J637.465D
• Wikidata: Q76006033
• Mol file: 16196-82-0.mol

Synonyms:16196-82-0;EINECS 240-326-2;1-[(1S,2S,6R,14R,15R,16S)-11,15-Dimethoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-16-yl]ethanone;1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone;C23H29NO4;1-[(5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone;6,14-endo-Ethanotetrahydrothebaine, 7.alpha.-acetyl-;SCHEMBL1722747;DTXSID40936617;Ethanone, 1-((5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)-;Ethanone, 1-[(5.alpha.,7.alpha.)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]-;7alpha-acetyl-6,14-endo-ethanotetrahydrothebaine;(14S)-3,6-Dimethoxy-7alpha-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan;1-(7,9-Dimethoxy-3-methyl-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methano[1]benzofuro[3,2-e]isoquinolin-6-yl)ethan-1-one

Chemical Property of 1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone

Chemical Property:

• Boiling Point: 518.1°Cat760mmHg
• Flash Point: 267.1°C
• PSA: 48.00000
• Density: 1.29g/cm³
• LogP: 2.66640
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 383.20965841
• Heavy Atom Count: 28
• Complexity: 713

Purity/Quality:

99.9% ^*data from raw suppliers

Dihydrothevinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)OC)O4)C)OC
• Isomeric SMILES: CC(=O)[C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)OC)O4)C)OC
• Uses: Intermediate in the preparation of Buprenorphine derivatives and analgesic compounds.

Technology Process of 1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone

There total 13 articles about 1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone 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%

Thevinon → 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine (16196-82-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In toluene; at 55 ℃; for 1.5h; under 4500.4 Torr;

DOI:10.1007/BF00813809

Reference yield: 94.5%

thevinone (15358-22-2) → 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine (16196-82-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; acetic acid; In water; at 20 ℃; for 18h; under 2250.23 Torr;

Reference yield: 83.0%

C23H31NO4 → 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine (16196-82-0)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 2h; Heating;

DOI:10.1007/BF00813809

upstream raw materials:

thevinone

7α-acetyl-6,14-endoethanotetrahydrothebaine

thebaine

N-carboethoxythebaine

Downstream raw materials:

diprenorphine

Dihydroetorphine

(2′R,5α,6R,7R,14α)-2′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethano-morphinan-7-yl)-3′-cyclohexyl-propan-2′-ol

(2′R,5α,6R,7R,14α)-2′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethano-morphinan-7-yl)-4′-cyclohexyl-butan-2′-ol

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF BUPRENORPHINE". Paragraph 13-14. . Retrieved 2021/08/06.
• 2、 -. "PROCESS FOR THE PREPARATION OF OPIOID COMPOUNDS". Paragraph 0159; 0161. . Retrieved 2015/11/27.