diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

Base Information

Chemical Name:diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate
CAS No.:1643565-84-7
Molecular Formula:C₂₀H₂₄O₅
Molecular Weight:344.408
Hs Code.:

Synonyms:diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

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Chemical Property of diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

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Technology Process of diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

There total 4 articles about diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate 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:

: 28937-18-0
4-methyl-4-phenyl-cyclohex-2,5-dien-1-one

: 105-53-3
diethyl malonate

: 1643565-84-7
diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

: diethyl 2-((1S,2S)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

: 1643566-01-1
diethyl 2-((1R,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

Guidance literature:: With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; In toluene; at 20 ℃; for 48h; Overall yield = 11 %; enantioselective reaction; Inert atmosphere;
DOI:10.1039/c4ob00733f

Reference yield:

: 17429-36-6
4-methyl-4-phenylcyclohex-2-enone

: 1643565-84-7
diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Phenylselenyl chloride; diisopropylamine; n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea / toluene / 48 h / 20 °C / Inert atmosphere

With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; n-butyllithium; Phenylselenyl chloride; diisopropylamine; In tetrahydrofuran; toluene;
DOI:10.1039/c4ob00733f

Reference yield:

: 28937-18-0
4-methyl-4-phenyl-cyclohex-2,5-dien-1-one

: 105-53-3
diethyl malonate

: 1643565-84-7
diethyl 2-((1S,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

: diethyl 2-((1R,2S)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

: diethyl 2-((1S,2S)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

: 1643566-01-1
diethyl 2-((1R,2R)-1-methyl-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)malonate

Guidance literature:: With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; In toluene; at 20 ℃; for 48h; Overall yield = 54 %; enantioselective reaction; Inert atmosphere;
DOI:10.1039/c4ob00733f