(+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

Base Information

Chemical Name:(+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one
CAS No.:226912-84-1
Molecular Formula:C₂₇H₂₈F₃NO₂
Molecular Weight:455.52
Hs Code.:

Synonyms:(+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

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Chemical Property of (+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

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Technology Process of (+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

There total 15 articles about (+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one 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:

: 226914-76-7
(3R,3aS,4S,4aR,8aS,9aR)-trifluoromethanesulfonic acid 6-[2-(3-methyl-1-oxododecahydronaphtho[2,3-c]furan-4-yl)vinyl]pyridin-3-yl ester

: 401-78-5
3-bromo-1-trifluoromethylbenzene

: 226912-84-1
(+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

Guidance literature:: (3R,3aS,4S,4aR,8aS,9aR)-trifluoromethanesulfonic acid 6-[2-(3-methyl-1-oxododecahydronaphtho[2,3-c]furan-4-yl)vinyl]pyridin-3-yl ester; With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; bis(pinacol)diborane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 80 ℃; for 2h;

3-bromo-1-trifluoromethylbenzene; With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 80 ℃; for 16h;
DOI:10.1021/jm0502236

Reference yield:

: 226915-53-3
(2R)-4-hydroxypentyl-2-ynoic acid benzyl ester

: 226912-84-1
(+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C

2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr

3.1: xylene / 6 h / 210 °C

3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C

4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr

5.1: SOCl₂ / toluene / 16 h / 80 °C

5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h

6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C

6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C

7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)*CH₂Cl₂ / dioxane / 2 h / 80 °C

9.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)*CH₂Cl₂ / dioxane / 16 h / 80 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; 4-pyrrolidin-1-ylpyridine; triethylamine; dicyclohexyl-carbodiimide; bis(pinacol)diborane; platinum(IV) oxide; Lindlar's catalyst; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; toluene; xylene; 3.1: Diels-Alder reaction / 6.2: Horner-Wadsworth-Emmons reaction / 9.2: Suzuki coupling;
DOI:10.1021/jm0502236

Reference yield:

: 1029100-88-6
2-methyl-5-triisopropylsilanyloxypyridine

: 226912-84-1
(+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: 68 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C

2.2: tetrahydrofuran; hexane / 0.17 h / 20 °C

3.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C

4.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

5.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)*CH₂Cl₂ / dioxane / 2 h / 80 °C

5.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)*CH₂Cl₂ / dioxane / 16 h / 80 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; tetrabutyl ammonium fluoride; potassium acetate; triethylamine; bis(pinacol)diborane; lithium diisopropyl amide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; 2.2: Horner-Wadsworth-Emmons reaction / 5.2: Suzuki coupling;
DOI:10.1021/jm0502236