5-Oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine

Base Information

• Chemical Name: 5-Oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine
• CAS No.: 612065-04-0
• Molecular Formula: C9H8F3NO4S
• Molecular Weight: 283.228
• DSSTox Substance ID: DTXSID80463119
• Wikidata: Q82287905
• Mol file: 612065-04-0.mol

Synonyms:612065-04-0;5-OXO-6-TRIFLUOROMETHANESULFONYLOXY-1,2,3,5-TETRAHYDROINDOLIZINE;(5-oxo-2,3-dihydro-1H-indolizin-6-yl) trifluoromethanesulfonate;5-Oxo-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonate;DTXSID80463119;5-Oxo-1,2,3,5-tetrahydroindolizin-6-yltrifluoromethanesulfonate

Chemical Property of 5-Oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine

Chemical Property:

• PSA: 73.75000
• LogP: 2.10370
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 283.01261340
• Heavy Atom Count: 18
• Complexity: 541

Purity/Quality:

95%-98% ^*data from raw suppliers

5-OXO-6-TRIFLUOROMETHANESULFONYLOXY-1,2,3,5-TETRAHYDROINDOLIZINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=C(C(=O)N2C1)OS(=O)(=O)C(F)(F)F

Technology Process of 5-Oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine

There total 7 articles about 5-Oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine 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: 89.0%

trifluoromethylsulfonic anhydride (358-23-6) + 6-hydroxy-2,3-dihydro-1H-indolizin-5-one (253195-68-5) → trifluoro-methanesulfonic acid 5-oxo-1,2,3,5-tetrahydro-indolizin-6-yl ester (612065-04-0)

Guidance literature:

With pyridine;

DOI:10.1039/b516154a

Reference yield:

phenylbis[(trifluoromethyl)sulfonyl]amine + 6-hydroxy-2,3-dihydro-1H-indolizin-5-one (253195-68-5) → trifluoro-methanesulfonic acid 5-oxo-1,2,3,5-tetrahydro-indolizin-6-yl ester (612065-04-0)

Guidance literature:

With triethylamine; at 0 - 20 ℃; for 18h;

Reference yield:

1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one (185198-40-7) → trifluoro-methanesulfonic acid 5-oxo-1,2,3,5-tetrahydro-indolizin-6-yl ester (612065-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Rh(II)

2: hydrobromic acid / Heating

3: Et₃N

With hydrogen bromide; triethylamine; rhodium⁽²⁺⁾;

DOI:10.1021/jo0511492

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

6-hydroxy-2,3-dihydro-1H-indolizin-5-one

trifluoromethylsulfonic anhydride

6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester

Downstream raw materials:

6-(pyridin-2-ylamino)-2,3-dihydro-1H-indolizin-5-one

N-(5-oxo-1,2,3,5-tetrahydro-indolizin-6-yl)-benzamide

1,2,3,6-tetrahydroindolizino[6,7-b]indol-5-one

6-(2-trifluoromethyl-phenylamino)-2,3-dihydro-1H-indolizin-5-one

Refernces

• 1、 Babjak, Matej,Kanazawa, Alice,Anderson, Regan J.,Greene, Andrew E.. "Concise synthesis of 22-hydroxyacuminatine, cytotoxic camptothecinoid from Camptotheca acuminata, by pyridone benzannulation". . p. 407 - 409. Retrieved 2007/10/03.