(E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone

Base Information

• Chemical Name: (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone
• CAS No.: 212690-57-8
• Molecular Formula: C₁₉H₂₂N₂O₅S
• Molecular Weight: 390.46

Synonyms:(E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone

Chemical Property of (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone

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Technology Process of (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone

There total 1 articles about (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone 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: 77.0%

(2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) + (E)-4-nitrocinnamic acid chloride (22440-58-0,61921-33-3) → (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone (212690-57-8)

Guidance literature:

With silver cyanide; In toluene; for 8h; Heating;

DOI:10.1002/hlca.19980810537

Reference yield:

(E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone (212690-57-8) → (2R,2'R,3'R)-N-[3'-azido-2'-bromo-3'-(4-nitrophenyl)propionyl]bornane-10,2-sultam + (2R,2'S,3'S)-N-[3'-azido-2'-bromo-3'-(4-nitrophenyl)propionyl]bornane-10,2-sultam

Guidance literature:

With N-Bromosuccinimide; trimethylsilylazide; ytterbium(III) triflate; In dichloromethane; at 45 ℃; for 36h; Title compound not separated from byproducts;

DOI:10.1021/jo061593k

Reference yield:

nitromethane (75-52-5) + (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-(4-nitro-phenyl)-propenone (212690-57-8) → (3S)-4-nitro-3-(4-nitrophenyl)-1-[ (3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]butan-1-one + (3R)-4-nitro-3-(4-nitrophenyl)-1-[ (3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]butan-1-one (1357375-12-2)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 24h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/hlca.201100197

upstream raw materials:

(2R)-bornane-10,2-sultam

(E)-4-nitrocinnamic acid chloride

Downstream raw materials:

(2R,3S)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester

(3R)-4-nitro-3-(4-nitrophenyl)-1-[ (3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]butan-1-one

(3R)-3-(4-nitrophenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]pentan-1-one

C₁₂H₁₃N₃O₃

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