(3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

Base Information

Chemical Name:(3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one
CAS No.:1579952-81-0
Molecular Formula:C₂₈H₂₈F₃NO₂
Molecular Weight:467.531
Hs Code.:

Synonyms:(3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

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Chemical Property of (3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

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Technology Process of (3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

There total 1 articles about (3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[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: 51.0%

: (3R,3aS,4S,4aR,8aR,9aR)-octahydro-3-methyl-4-[(E)-2-[5-[3-(trifluoromethyl)phenyl]-2-pyridinyl]ethenyl]naphtho[2,3-c]furan-1,7(3H,4H)-dione

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1579952-81-0
(3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

Guidance literature:: Methyltriphenylphosphonium bromide; With phenyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.5h; Inert atmosphere;

(3R,3aS,4S,4aR,8aR,9aR)-octahydro-3-methyl-4-[(E)-2-[5-[3-(trifluoromethyl)phenyl]-2-pyridinyl]ethenyl]naphtho[2,3-c]furan-1,7(3H,4H)-dione; In tetrahydrofuran; at 20 ℃; for 2.25h; Inert atmosphere;
DOI:10.1021/ml500008w

Reference yield: 29.0%

: 1579952-81-0
(3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

: 1579952-82-1
C₂₈H₃₀F₃NO₃

Guidance literature:: (3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one; With 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 ℃; for 5h; Inert atmosphere;

With sodium peroxoborate tetrahydrate; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;
DOI:10.1021/ml500008w

Reference yield:

: 1579952-81-0
(3R,3aS,4S,4aR,8aR,9aR)-3-methyl-7-methylene-4-((E)-2-(5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)vinyl)decahydronaphtho[2,3-c]furan-1(3H)-one

: 1579952-89-8
2-(6-((E)-2-((1R,3aR,4aR,4'R,8aR,9S,9aS)-1-methyl-2',3-dioxodecahydro-1H-spiro[naphtho[2,3-c]furan-6,4'-oxazolidin]-9-yl)vinyl)pyridin-3-yl)benzonitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: dichloromethane / 0.58 h / Inert atmosphere

2.2: 0.75 h / Inert atmosphere

3.1: [bis(acetoxy)iodo]benzene; dirhodium tetraacetate; magnesium oxide / dichloromethane / Inert atmosphere; Reflux

4.1: ozone / dichloromethane; methanol / 0.17 h / -78 °C / Inert atmosphere

4.2: air / 0.5 h

4.3: 0.5 h / 20 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

5.2: 1.67 h / 0 - 20 °C / Inert atmosphere

6.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene; ethanol / 20 - 80 °C / Inert atmosphere

With dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [bis(acetoxy)iodo]benzene; magnesium oxide; potassium carbonate; ozone; 9-borabicyclo[3.3.1]nonane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; 6.1: |Suzuki Coupling;
DOI:10.1021/ml500008w