(-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one

Base Information

• Chemical Name: (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one
• CAS No.: 1173107-91-9
• Molecular Formula: C₁₉H₂₂O
• Molecular Weight: 266.383
• Mol file: 1173107-91-9.mol

Synonyms:(-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one

Chemical Property of (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one

There total 3 articles about (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-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: 92.0%

trans-4,4'-dimethylchalcone (13565-37-2) + diethylzinc (557-20-0) → (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one (1173107-91-9)

Guidance literature:

With (S)-N-((1R,2R)-2-(diphenylphosphino)cyclohexyl)pyrrolidine-2-carboxamide; copper(II) acetate monohydrate; In diethyl ether; hexane; at 0 ℃; for 1h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2019.05.029

Reference yield: 92.0%

4,4'-Dimethylchalcon (21551-47-3) → (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one (1173107-91-9)

Guidance literature:

4,4'-Dimethylchalcon; With C₄₁H₃₂NO₂P; copper(II) bis(trifluoromethanesulfonate); In diethyl ether; at -20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

With diethylzinc; In diethyl ether; at -20 ℃; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/asia.201300544

Reference yield:

C22H31NO3S (1041477-73-9) + para-methylphenylmagnesium bromide (4294-57-9) → (-)-(3R)-1,3-bis(4-methylphenyl)-pentan-1-one (1173107-91-9) + C19H22O

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/hlca.200800375

upstream raw materials:

C₂₂H₃₁NO₃S

para-methylphenylmagnesium bromide

4,4'-Dimethylchalcon

trans-4,4'-dimethylchalcone

Refernces

• 1、 Rexiti, Rukeya,Lu, Jian,Sha, Feng,Wu, Xin-Yan. "Copper-catalyzed enantioselective 1,4-conjugate addition of dialkylzinc reagents to α,β- and α,β,γ,δ-unsaturated ketones". . p. 3596 - 3604. Retrieved 2019/06/04.