(3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline

Base Information

• Chemical Name: (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline
• CAS No.: 1579277-32-9
• Molecular Formula: C₂₉H₂₅N₃O₄S₂
• Molecular Weight: 543.667

Synonyms:

Chemical Property of (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline

There total 3 articles about (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline 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:

N-phenyl-maleimide (941-69-5) + N-(2,4,6-trimethylbenzenesulfonyl)-2-mercaptoquinoline-3-carbaldimine (1579277-07-8) → (3aS,11S,11aS)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline (1579277-17-0) + (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline (1579277-32-9)

Guidance literature:

With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In dichloromethane; at -40 ℃; for 4h; Solvent; Time; Overall yield = 93 %; stereoselective reaction; Molecular sieve;

DOI:10.1002/cctc.201300993

Reference yield:

3-formyl-2-mercaptoquinoline (51925-41-8) → (3aS,11S,11aS)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline (1579277-17-0) + (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline (1579277-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / toluene / 8 h / 20 °C / Reflux; Dean-Stark

2: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / dichloromethane / 4 h / -40 °C / Molecular sieve

With toluene-4-sulfonic acid; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In dichloromethane; toluene;

DOI:10.1002/cctc.201300993

Reference yield:

2,4,6-trimethylbenzenesulfonamide (4543-58-2) → (3aS,11S,11aS)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline (1579277-17-0) + (3aR,11R,11aR)-1,3-dioxo-2-phenyl-11-(2,4,6-trimethylbenzenesulfonamido)-1,2,3,3a,11,11a-hexahydropyrrolo[3',4':5,6]thiopyrano[2,3-b]quinoline (1579277-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / toluene / 8 h / 20 °C / Reflux; Dean-Stark

2: 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / dichloromethane / 4 h / -40 °C / Molecular sieve

With toluene-4-sulfonic acid; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In dichloromethane; toluene;

DOI:10.1002/cctc.201300993

upstream raw materials:

N-phenyl-maleimide

N-(2,4,6-trimethylbenzenesulfonyl)-2-mercaptoquinoline-3-carbaldimine

2,4,6-trimethylbenzenesulfonamide

3-formyl-2-mercaptoquinoline

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