(1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Base Information

Chemical Name:(1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene
CAS No.:1423043-24-6
Molecular Formula:C₁₇H₁₉NO₃
Molecular Weight:285.343
Hs Code.:

Synonyms:(1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

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Chemical Property of (1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

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Technology Process of (1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

There total 5 articles about (1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene 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: 62.0%

: 636-98-6
p-nitrobenzene iodide

: potassium trifluoro((1S,4R,8R)-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-dien-2-yl)borate

: 1423043-24-6
(1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Guidance literature:: With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate; In tetrahydrofuran; water; at 85 ℃; for 16h; Inert atmosphere; Sealed tube;
DOI:10.1021/acs.orglett.9b01609

Reference yield: 55.0%

: 24067-17-2
4-nitrophenylboronic acid

: 913697-08-2
trifluoro-methanesulfonic acid 8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-dien-2-yl ester

: 1423043-24-6
(1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Guidance literature:: With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 2.5h; Inert atmosphere;
DOI:10.1021/ol400363f

Reference yield:

: ((1S,4S,8R)-8-methoxy-1,8-dimethylbicyclo[2.2.2]oct-5-en-2-ylidene)hydrazine

: 1423043-24-6
(1S,4R,5R)-2-(4-nitrophenyl)-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: iodine; 1,4-diaza-bicyclo[2.2.2]octane / diethyl ether / 1.83 h / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / -78 - -60 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

2.3: Inert atmosphere

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate; potassium phosphate / tetrahydrofuran; water / 16 h / 85 °C / Inert atmosphere; Sealed tube

With 1,4-diaza-bicyclo[2.2.2]octane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; iodine; tricyclohexylphosphine tetrafluoroborate; In tetrahydrofuran; diethyl ether; water; 3.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.orglett.9b01609