185198-44-1

Basic information

• Product Name: 8-BENZENESULFONYL-5-OXO-1,2,3,5-TETRAHYDROINDOLIZIN-6-YL TRIFLUOROMETHANESULFONATE
• Synonyms: 8-BENZENESULFONYL-5-OXO-1,2,3,5-TETRAHYDROINDOLIZIN-6-YL TRIFLUOROMETHANESULFONATE
• CAS NO: 185198-44-1
• Molecular Formula: C₁₅H₁₂F₃NO₆S₂
• Molecular Weight: 423.38
• Product Categories: pharmacetical
• Mol File: 185198-44-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 573.7°Cat760mmHg
• Flash Point: 300.8°C
• Appearance: /
• Density: 1.69g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 8-BENZENESULFONYL-5-OXO-1,2,3,5-TETRAHYDROINDOLIZIN-6-YL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BENZENESULFONYL-5-OXO-1,2,3,5-TETRAHYDROINDOLIZIN-6-YL TRIFLUOROMETHANESULFONATE(185198-44-1)
• EPA Substance Registry System: 8-BENZENESULFONYL-5-OXO-1,2,3,5-TETRAHYDROINDOLIZIN-6-YL TRIFLUOROMETHANESULFONATE(185198-44-1)

Safety Data

• Hazardous Substances Data: 185198-44-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H12F3NO6S2/c16-15(17,18)27(23,24)25-12-9-13(11-7-4-8-19(11)14(12)20)26(21,22)10-5-2-1-3-6-10/h1-3,5-6,9H,4,7-8H2

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 185198-43-0 8-(phenylsulfonyl)-6-hydroxy-2,3-dihydro-1H-indolizin-5-one 
• 907969-47-5 1-(phenylsulfonylacetyl)pyrrolidin-2-one 
• 5535-48-8 PVS 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 185198-40-7 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one 

Downstream Products

• 612065-27-7 8-benzenesulfonyl-6-(3,5-dimethoxy-phenylamino)-2,3-dihydro-1H-indolizin-5-one 
• 612065-26-6 8-benzenesulfonyl-6-(4-nitro-phenylamino)-2,3-dihydro-1H-indolizin-5-one 
• 612065-29-9 8-benzenesulfonyl-6-(pyridin-2-ylamino)-2,3-dihydro-1H-indolizin-5-one 
• 185198-45-2 8-phenylsulfonyl-6-phenyl-2,3-dihydro-1H-indolizin-5-one 
• 612065-28-8 8-benzenesulfonyl-6-(2-trifluoromethyl-phenylamino)-2,3-dihydro-1H-indolizin-5-one 
• 612065-24-4 8-benzenesulfonyl-6-phenylamino-2,3-dihydro-1H-indolizin-5-one 

Relevant articles and documents

1,3-Dipolar cycloaddition chemistry for the preparation of novel indolizinone-based compounds

Starting from methyl 5-oxo-6-trifluoromethanesulfonyloxy-1,2,3,5- tetrahydroindolizine-8-carboxylate, obtained by a Rh(II)-catalyzed 1,3-dipolar cycloaddition reaction of 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one and methyl acrylate, several indolo- and furano-fused indolizinones were efficiently prepared. In the first case, a palladium-mediated C-N coupling of the triflate with a variety of substituted anilines provided the desired methyl 5-oxo-6-(arylamino)-1,2,3,5-tetrahydroindolizine-8-carboxylates in high yield. Methyl 6-(2-bromophenylamino)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate as well as its decarboxylated analogue, 6-(2-bromophenylamino)-2,3-dihydro-1H- indolizin-5-one, were synthesized in excellent yield and were found to undergo an intramolecular Heck cyclization to give 1,2,3,6-tetrahydroindolizino[6,7-b] indol-5-ones. To prepare furano-fused indolizinones, methyl 6-hydroxy-5-oxo-1,2, 3,5-tetrahydroindolizine-8-carboxylate was etherified with different allyl halides, and the resultant allyl ethers were subjected to a thermal Claisen rearrangement to give the corresponding methyl 7-allyl-6-hydroxy-5-oxo-1,2,3,4- tetrahydroindolizine-8-carboxylates. Cyclization under Wacker oxidation conditions afforded methyl 2-methyl-8-oxo-5,6,7,8-tetrahydro-1-oxa-7a-aza-s- indacene-4-carboxylates in near-quantitative yield.

New synthetic route to 2-pyridones and its application toward the synthesis of (±)-ipalbidine

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