(1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

Base Information

Chemical Name:(1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate
CAS No.:1374793-36-8
Molecular Formula:C₁₅H₁₃F₃O₃S
Molecular Weight:330.328
Hs Code.:

Synonyms:(1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

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Technology Process of (1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

There total 3 articles about (1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate 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: 98.0%

: 132486-17-0,130913-07-4
(1R,4R)-5-phenylbicyclo[2.2.2]oct-5-en-2-one

: 145100-50-1
1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methane sulfonamide

: 1374793-36-8
(1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 - 0 ℃; for 3h; Schlenk technique; Inert atmosphere;
DOI:10.1021/jacs.1c03498

Reference yield:

: N-(5-chloro-2-pyridyl)triflimide

: 132486-17-0,130913-07-4
(1R,4R)-5-phenylbicyclo[2.2.2]oct-5-en-2-one

: 1374793-36-8
(1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

Guidance literature:: (1R,4R)-5-phenylbicyclo[2.2.2]oct-5-en-2-one; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 1h; Inert atmosphere;

N-(5-chloro-2-pyridyl)triflimide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/jo3005638

Reference yield:

: 930-68-7
cyclohexenone

: 1374793-36-8
(1R,4R)-5-phenylbicyclo[2.2.2]octa-2,5-dien-2-yl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; L-proline / toluene / 96 h / 0 °C / Inert atmosphere

2.1: triethylamine / toluene / 0.17 h / 10 - 20 °C / Inert atmosphere

3.1: 2,4,6-trimethyl-pyridine / 1.33 h / 140 - 145 °C / Inert atmosphere

4.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - -20 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

With 2,4,6-trimethyl-pyridine; n-butyllithium; triethylamine; N-ethyl-N,N-diisopropylamine; L-proline; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo3005638