1-Pentanone, 1,3-diphenyl-, (3R)-

Base Information

• Chemical Name: 1-Pentanone, 1,3-diphenyl-, (3R)-
• CAS No.: 115730-45-5
• Molecular Formula: C17H18O
• Molecular Weight: 238.329
• Mol file: 115730-45-5.mol

Synonyms:

Chemical Property of 1-Pentanone, 1,3-diphenyl-, (3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Pentanone, 1,3-diphenyl-, (3R)-

There total 60 articles about 1-Pentanone, 1,3-diphenyl-, (3R)- 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: 100.0%

diethylzinc (557-20-0) + 1,3-diphenyl-propen-3-one (614-47-1) → 1,3-diphenylpentan-1-one (16460-86-9,76156-05-3,115730-45-5,1454-61-1)

Guidance literature:

With copper(I) trifluoromethanesulfonate benzene complex; In diethyl ether; hexane; at -20 ℃; for 22h;

DOI:10.1039/c003352a

Reference yield: 98.0%

diethylzinc (557-20-0) + 1,3-diphenyl-propen-3-one (614-47-1) → (R)-1,3-diphenylpentan-1-one (115730-45-5)

Guidance literature:

diethylzinc; With C₅₄H₃₇N₂O₂P; copper(II) acetylacetonate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

1,3-diphenyl-propen-3-one; In tetrahydrofuran; at 0 ℃; for 0.5h; Reagent/catalyst; Solvent; Time; Concentration; enantioselective reaction; Inert atmosphere;

DOI:10.1055/s-0033-1338439

Reference yield: 96.0%

diethylzinc (557-20-0) + benzalacetophenone (94-41-7) → (R)-1,3-diphenylpentan-1-one (115730-45-5)

Guidance literature:

diethylzinc; With C₄₈H₅₀N₂O₄P₂; copper diacetate; In hexane; toluene; at -50 ℃; for 0.0833333h; Inert atmosphere;

benzalacetophenone; In hexane; toluene; at -50 ℃; for 16h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/c2ob25730k

upstream raw materials:

ethylmagnesium bromide

benzalacetophenone

(1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone

lithium dimethylcuprate

Downstream raw materials:

(1-ethylpropyl)benzene

2-methyl-1,3-diphenyl-pentan-1-one

2-ethyl-1,3-diphenyl-pentan-1-one

1,3-diphenyl-pentan-1-one oxime

Refernces

• 1、 Jensen, Jakob F.,Sotofte, Inger,Sorensen, Henning O.,Johannsen, Mogens. "Modular approach to novel chiral aryl-ferrocenyl phosphines by Suzuki cross-coupling". . p. 1258 - 1265. Retrieved 2003.
• 2、 Brüllingen, Eric,Neud?rfl, J?rg-Martin,Goldfuss, Bernd. "Enantioselective Cu-catalyzed 1,4-additions of organozinc and Grignard reagents to enones: Exceptional performance of the hydrido-phosphite-ligand BIFOP-H". . p. 4787 - 4799. Retrieved 2019.
• 3、 Yin, Long,Xing, Junhao,Wang, Yuhan,Shen, Yue,Lu, Tao,Hayashi, Tamio,Dou, Xiaowei. "Enantioselective Synthesis of 3,3′-Diaryl-SPINOLs: Rhodium-Catalyzed Asymmetric Arylation/BF3-Promoted Spirocyclization Sequence". . p. 2474 - 2478. Retrieved 2019.
• 4、 Dogan, Oezdemir,Bulut, Adnan,Polat, Sava,Ali Tecimer. "Copper-catalyzed asymmetric conjugate addition of diethylzinc to substituted chalcones using a chiral phosphine ligand". . p. 1601 - 1604. Retrieved 2011.
• 5、 Rachwalski, Michal,Jarzynski, Szymon,Lesniak, Stanislaw. "Highly efficient conjugate addition of diethylzinc to enones catalyzed by chiral ligands derived from (S)-mandelic acid". . p. 1117 - 1119. Retrieved 2013.
• 6、 Reetz, Manfred T.,Gosberg, Andreas,Moulin, Dominique. "Copper-catalyzed enantioselective conjugate addition of diethylzinc to α,β-unsaturated carbonyl compounds using diphosphonites as chiral ligands". . p. 1189 - 1191. Retrieved 2002.
• 7、 Rachwalski, Michal,Lesniak, Stanislaw,Kielbasinski, Piotr. "Highly enantioselective conjugate addition of diethylzinc to enones usingaziridine-functionalized tridentate sulfinyl ligands". . p. 1890 - 1892. Retrieved 2010.
• 8、 Wakimoto, Izumi,Tomioka, Yuko,Kawanami, Yasuhiro. "Catalytic enantioselective conjugate addition of diethylzinc to chalcones using chiral amino alcohol-nickel complexes". . p. 8095 - 8097. Retrieved 2002.
• 9、 Tauchman, Jiri,Cisarova, Ivana,Stepnicka, Petr. "Chiral phosphanylferrocenecarboxamides with amino acid pendant groups as ligands for Cu-mediated asymmetric conjugate additions of diethylzinc to chalcones - Structural characterisation of precursors to the Cu catalyst". . p. 4276 - 4287. Retrieved 2010.
• 10、 Jansen,Feringa. "Catalytic enantioselective conjugate addition of diethylzinc using Ni(II)-DAIB complexes". . p. 581 - 582. Retrieved 1992.