(+/-)-aspidofractinine

Base Information

• Chemical Name: (+/-)-aspidofractinine
• CAS No.: 60365-41-5
• Molecular Formula: C₁₉H₂₄N₂
• Molecular Weight: 280.413
• Mol file: 60365-41-5.mol

Synonyms:

Chemical Property of (+/-)-aspidofractinine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-aspidofractinine

There total 52 articles about (+/-)-aspidofractinine 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: 91.0%

N(1)-formyl-aspidofractinine → (+/-)-aspidofractinine (6871-25-6,60365-41-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 70 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.202009238

Reference yield: 76.0%

5-Oxoaspidofractinine → (+/-)-aspidofractinine (6871-25-6,60365-41-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo00104a023

Reference yield:

C19H22N2O → (+/-)-aspidofractinine (6871-25-6,60365-41-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: potassium hydroxide / tetrahydrofuran; methanol; water / 12 h / 0 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere

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

4.1: lithium carbonate; lithium chloride / N,N-dimethyl-formamide / 10 h / 90 °C / Inert atmosphere; Molecular sieve

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: potassium osmate(VI); 4-methylmorpholine N-oxide / water; acetonitrile / 5 h / 20 °C / Inert atmosphere

6.2: 0.25 h / 0 °C / Inert atmosphere

7.1: pyridine hydrochloride / dichloromethane; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

8.1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

9.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

10.1: Martins sulfurane / dichloromethane / 0 - 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / Inert atmosphere

12.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

13.1: platinum(IV) oxide; hydrogen / ethyl acetate / 20 °C

14.1: hydrazine hydrate; sodium / ethylene glycol / 4 h / 160 - 210 °C / Inert atmosphere

15.1: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

16.1: acetic acid / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

16.2: -78 - 0 °C / Inert atmosphere

17.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 70 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; platinum(IV) oxide; aluminum (III) chloride; potassium osmate(VI); lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1,3-dimethylbarbituric acid; Martins sulfurane; tetrabutyl ammonium fluoride; hydrogen; pyridine hydrochloride; sodium; lithium carbonate; Dess-Martin periodane; hydrazine hydrate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; lithium chloride; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethylene glycol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 14.1: |Wolff-Kishner Reduction;

DOI:10.1002/anie.202009238

upstream raw materials:

(+/-)-20-oxoaspidofractinine

C₁₉H₂₂N₂O

(3aS,10bS,12bR)-2,3,3a,12b-Tetrahydro-1H,6H-6,12a-diaza-indeno[7,1-cd]fluorene-4,12-dione

20-deethyl-2,16-didehydro-5,17-dioxo-1-(p-tolylsulfonyl)aspidospermidine