(19E)-1-Acetyl-19,20-didehydro-17-norcuran-16-one

Base Information

• Chemical Name: (19E)-1-Acetyl-19,20-didehydro-17-norcuran-16-one
• CAS No.: 76177-20-3
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.407
• Mol file: 76177-20-3.mol

Synonyms:3,5-Ethano-3H-pyrrolo[2,3-d]carbazole,17-norcuran-16-one deriv.; Strychnopivotine

Chemical Property of (19E)-1-Acetyl-19,20-didehydro-17-norcuran-16-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (19E)-1-Acetyl-19,20-didehydro-17-norcuran-16-one

There total 10 articles about (19E)-1-Acetyl-19,20-didehydro-17-norcuran-16-one 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: 20.0%

(3aS,6aR,11bR)-7-acetyl-3-((Z)-2-iodobut-2-en-1-yl)-3,3a,4,5,6a,7-hexahydro-1H-pyrrolo[2,3-d]carbazol-6(2H)-one → (-)-strychnopivotine (76177-20-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In methanol; at 70 ℃; Inert atmosphere;

DOI:10.1002/chem.201601319

Reference yield:

C18H20N2O + acetic anhydride (108-24-7) → (+/-)-strychnopivotine (76177-20-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/jo8003716

Reference yield:

(3aS,5R,5aR,5a1R,7R,13bR)-5-(dimethyl(phenyl)silyl)-3-((Z)-2-iodobut-2-en-1-yl)-5amethoxy-7-methyl-2,3,3a,4,5,5a,5a1,7-octahydro-[1,4]oxazino[4,3,2-lm]pyrrolo[2,3-d]carbazol-8(1H)-one → (-)-strychnopivotine (76177-20-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic acid; hydrogenchloride / water / 50 °C

2.1: sodium tetrahydroborate / ethanol / 0 - 20 °C

3.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C

5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 1 h / 20 °C

6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / methanol / 70 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; tetrapropylammonium perruthennate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; In methanol; ethanol; dichloromethane; water; acetonitrile; 5.1: |Ley-Griffith Ru Oxidation / 6.1: |Heck Reaction;

DOI:10.1002/chem.201601319

upstream raw materials:

acetic anhydride