(1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

Base Information

Chemical Name:(1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone
CAS No.:1378427-97-4
Molecular Formula:C₂₄H₂₃F₃O₃S
Molecular Weight:448.506
Hs Code.:

Synonyms:(1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

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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,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

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Technology Process of (1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

There total 3 articles about (1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone 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:

: 2161-90-2
1-methoxy-1,3-cyclohexadiene

: 1378383-75-5
(E,S)-4,4,4-trifluoro-1-[2-(p-tolylsulfinyl)phenyl]but-2-en-1-one

: 1378427-99-6
(1S,2S,3R,4S)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

: 1378427-97-4
(1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

Guidance literature:: With ytterbium(III) triflate; In acetonitrile; at 20 ℃; for 8h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2012.03.112

Reference yield:

: C₁₈H₂₂O₂SSi

: 1378427-99-6
(1S,2S,3R,4S)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

: 1378427-97-4
(1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

Guidance literature:: Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

2: ytterbium(III) triflate / acetonitrile / 8 h / 20 °C

With boron trifluoride diethyl etherate; ytterbium(III) triflate; In dichloromethane; acetonitrile; 2: Diels-Alder reaction;
DOI:10.1016/j.tet.2012.03.112

Reference yield:

: (S)-1-[2-(p-tolylsulfinyl)phenyl]ethanone

: 1378427-99-6
(1S,2S,3R,4S)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

: 1378427-97-4
(1R,2S,3R,4R)-1-methoxy-3-(trifluoromethyl)bicyclo[2.2.2]oct-5-en-2-yl-{2-[(S)-p-tolylsulfinyl]phenyl}methanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; n-heptane / 0.33 h / 20 °C / Inert atmosphere

1.2: 3 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

3.1: ytterbium(III) triflate / acetonitrile / 8 h / 20 °C

With boron trifluoride diethyl etherate; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; n-heptane; dichloromethane; acetonitrile; 3.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2012.03.112