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Cas Database

864148-47-0

864148-47-0

Identification

  • Product Name:(S)-(4E)-6-phenylhept-4-en-2-one

  • CAS Number: 864148-47-0

  • EINECS:

  • Molecular Weight:188.269

  • Molecular Formula: C13H16O

  • HS Code:

  • Mol File:864148-47-0.mol

Synonyms:(S)-(4E)-6-phenylhept-4-en-2-one

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Relevant articles and documentsAll total 3 Articles be found

Regio- and Enantioselective Copper-Catalyzed 1,4-Conjugate Addition of Trimethylaluminium to Linear α,β,γ,δ-Unsaturated Alkyl Ketones

Wu, Xiaoting,Xie, Fang,Ling, Zheng,Tang, Liang,Zhang, Wanbin

supporting information, p. 2510 - 2518 (2016/08/16)

A regio- and enantioselective copper-catalyzed 1,4-conjugate addition of trimethylaluminium to linear δ-aryl-substituted α,β,γ,δ-unsaturated alkyl ketones was developed. A series of γ,δ-unsaturated alkyl ketones were obtained in good yields with high regio- and enantioselectivity (up to 88% ee and 96:4 dr). Expansion of the reaction scope to substrates containing aromatic heterocycles also afforded good yields and enantioselectivities (up to 91% ee) with very high regioselectivities, exclusively providing the single 1,4-products. (Figure presented.).

Highly selective 1,6-addition of aryl boronic acids to α,β, γ,δ-unsaturated carbonyl compounds catalyzed by an indium complex

Nishimura, Takahiro,Yasuhara, Yuichi,Hayashi, Tamio

, p. 5164 - 5166 (2007/10/03)

(Chemical Equation Presented) Perfect control: The catalytic 1,6-addition of aryl boronic acids to electron-deficient dienes was realized by use of an iridium catalyst (see scheme). High yields of the corresponding δ-arylated carbonyl compounds were obtai

Rhodium-catalyzed asymmetric 1,6-addition of aryl zinc reagents to dienones

Hayashi, Tamio,Yamamoto, Shohei,Tokunaga, Norihito

, p. 4224 - 4227 (2007/10/03)

(Chemical Equation Presented) A highly enantioselective methodology allows the preparation of α,β-unsaturated ketones that contain a new stereogenic center at the C5 position. This approach is realized through the title reaction in the presence of chlorotrimethylsilane as a Lewis acid and a rhodium/(S)-binap complex as the catalyst followed by acidic hydrolysis (see scheme). binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl.

Process route upstream and downstream products

Process route

triphenylboroxine
3262-89-3

triphenylboroxine

(3E,5E)-3.5-heptadien-2-one
18402-90-9

(3E,5E)-3.5-heptadien-2-one

(Z)-6-phenyl-4-hepten-2-one

(Z)-6-phenyl-4-hepten-2-one

(5E)-6-phenyl-4-hepten-2-one
864148-47-0

(5E)-6-phenyl-4-hepten-2-one

4,4-diphenyl-2-heptanone

4,4-diphenyl-2-heptanone

(5E)-4-phenylhept-5-en-2-one
88343-87-7

(5E)-4-phenylhept-5-en-2-one

Conditions
Conditions Yield
With water; [Rh(OH)(cod)]2; In toluene; at 80 ℃; for 3h;
55%
triphenylboroxine
3262-89-3

triphenylboroxine

(3E,5E)-3.5-heptadien-2-one
18402-90-9

(3E,5E)-3.5-heptadien-2-one

(Z)-6-phenyl-4-hepten-2-one

(Z)-6-phenyl-4-hepten-2-one

(5E)-6-phenyl-4-hepten-2-one
864148-47-0

(5E)-6-phenyl-4-hepten-2-one

(E)-6-phenyl-3-hepten-2-one
344774-26-1

(E)-6-phenyl-3-hepten-2-one

4,4-diphenyl-2-heptanone

4,4-diphenyl-2-heptanone

Conditions
Conditions Yield
With water; [(1,5-cyclooctadiene)(OH)iridium(I)]2; In toluene; at 80 ℃; for 3h;
(3E,5E)-3.5-heptadien-2-one
18402-90-9

(3E,5E)-3.5-heptadien-2-one

phenyllithium
591-51-5

phenyllithium

(R)-(4E)-6-phenylhept-4-en-2-one

(R)-(4E)-6-phenylhept-4-en-2-one

(S)-(4E)-6-phenylhept-4-en-2-one
864148-47-0

(S)-(4E)-6-phenylhept-4-en-2-one

(R)-(3E)-6-phenylhept-3-en-2-one

(R)-(3E)-6-phenylhept-3-en-2-one

(S)-(3E)-6-phenylhept-3-en-2-one

(S)-(3E)-6-phenylhept-3-en-2-one

Conditions
Conditions Yield
phenyllithium; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at 20 ℃; for 0.5h;
(3E,5E)-3.5-heptadien-2-one; With chloro-trimethyl-silane; [Rh((S)-BINAP)Cl]2; In tetrahydrofuran; diethyl ether; cyclohexane; at 20 ℃; for 2h;
With hydrogenchloride; In tetrahydrofuran; diethyl ether; cyclohexane; Further byproducts given. Title compound not separated from byproducts;
(S)-(4E)-6-phenylhept-4-en-2-one
864148-47-0

(S)-(4E)-6-phenylhept-4-en-2-one

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: thionyl chloride
2.1: CuI / diethyl ether / 0.17 h / 0 °C
2.2: 38 percent / diethyl ether / 0.25 h / -78 °C
3.1: ZnCl2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / 20 °C
3.2: [RhCl((S)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)]2; ClSiMe3 / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 20 °C
3.3: aq. HCl / tetrahydrofuran; cyclohexane; diethyl ether
With copper(l) iodide; thionyl chloride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane;
sorbinyl chloride
2614-88-2

sorbinyl chloride

(S)-(4E)-6-phenylhept-4-en-2-one
864148-47-0

(S)-(4E)-6-phenylhept-4-en-2-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: CuI / diethyl ether / 0.17 h / 0 °C
1.2: 38 percent / diethyl ether / 0.25 h / -78 °C
2.1: ZnCl2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / 20 °C
2.2: [RhCl((S)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)]2; ClSiMe3 / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 20 °C
2.3: aq. HCl / tetrahydrofuran; cyclohexane; diethyl ether
With copper(l) iodide; zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane;
(E,E)-6-phenyl-3,5-hexadien-2-one
4173-44-8

(E,E)-6-phenyl-3,5-hexadien-2-one

trimethylaluminum
75-24-1

trimethylaluminum

(5E)-6-phenyl-4-hepten-2-one
864148-47-0

(5E)-6-phenyl-4-hepten-2-one

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one
1094836-36-8

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one

Conditions
Conditions Yield
With C48H50N2O4P2; copper(II) acetate monohydrate; In tetrahydrofuran; at -30 ℃; for 12h; Reagent/catalyst; regioselective reaction; Inert atmosphere;
87 % ee
triphenylboroxine
3262-89-3

triphenylboroxine

(3E,5E)-3.5-heptadien-2-one
18402-90-9

(3E,5E)-3.5-heptadien-2-one

(Z)-6-phenyl-4-hepten-2-one

(Z)-6-phenyl-4-hepten-2-one

(5E)-6-phenyl-4-hepten-2-one
864148-47-0

(5E)-6-phenyl-4-hepten-2-one

4,4-diphenyl-2-heptanone

4,4-diphenyl-2-heptanone

(5E)-4-phenylhept-5-en-2-one
88343-87-7

(5E)-4-phenylhept-5-en-2-one

Conditions
Conditions Yield
With water; [Rh(OH)(cod)]2; In toluene; at 80 ℃; for 3h;
55%
triphenylboroxine
3262-89-3

triphenylboroxine

(3E,5E)-3.5-heptadien-2-one
18402-90-9

(3E,5E)-3.5-heptadien-2-one

(Z)-6-phenyl-4-hepten-2-one

(Z)-6-phenyl-4-hepten-2-one

(5E)-6-phenyl-4-hepten-2-one
864148-47-0

(5E)-6-phenyl-4-hepten-2-one

(E)-6-phenyl-3-hepten-2-one
344774-26-1

(E)-6-phenyl-3-hepten-2-one

4,4-diphenyl-2-heptanone

4,4-diphenyl-2-heptanone

Conditions
Conditions Yield
With water; [(1,5-cyclooctadiene)(OH)iridium(I)]2; In toluene; at 80 ℃; for 3h;
(3E,5E)-3.5-heptadien-2-one
18402-90-9

(3E,5E)-3.5-heptadien-2-one

phenyllithium
591-51-5

phenyllithium

(R)-(4E)-6-phenylhept-4-en-2-one

(R)-(4E)-6-phenylhept-4-en-2-one

(S)-(4E)-6-phenylhept-4-en-2-one
864148-47-0

(S)-(4E)-6-phenylhept-4-en-2-one

(R)-(3E)-6-phenylhept-3-en-2-one

(R)-(3E)-6-phenylhept-3-en-2-one

(S)-(3E)-6-phenylhept-3-en-2-one

(S)-(3E)-6-phenylhept-3-en-2-one

Conditions
Conditions Yield
phenyllithium; With zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at 20 ℃; for 0.5h;
(3E,5E)-3.5-heptadien-2-one; With chloro-trimethyl-silane; [Rh((S)-BINAP)Cl]2; In tetrahydrofuran; diethyl ether; cyclohexane; at 20 ℃; for 2h;
With hydrogenchloride; In tetrahydrofuran; diethyl ether; cyclohexane; Further byproducts given. Title compound not separated from byproducts;
(S)-(4E)-6-phenylhept-4-en-2-one
864148-47-0

(S)-(4E)-6-phenylhept-4-en-2-one

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: thionyl chloride
2.1: CuI / diethyl ether / 0.17 h / 0 °C
2.2: 38 percent / diethyl ether / 0.25 h / -78 °C
3.1: ZnCl2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / 20 °C
3.2: [RhCl((S)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)]2; ClSiMe3 / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 20 °C
3.3: aq. HCl / tetrahydrofuran; cyclohexane; diethyl ether
With copper(l) iodide; thionyl chloride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane;

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