(S)-3-phenyl-1,4,5-hexatriene

Base Information

• Chemical Name: (S)-3-phenyl-1,4,5-hexatriene
• CAS No.: 1353901-30-0
• Molecular Formula: C₁₂H₁₂
• Molecular Weight: 156.227
• Mol file: 1353901-30-0.mol

Synonyms:(S)-3-phenyl-1,4,5-hexatriene

Chemical Property of (S)-3-phenyl-1,4,5-hexatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-3-phenyl-1,4,5-hexatriene

There total 3 articles about (S)-3-phenyl-1,4,5-hexatriene 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:

4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0) + (E)-cinnamyl diethyl phosphate (85669-63-2) → (S)-3-phenyl-1,4,5-hexatriene (1353901-30-0) + (E)-hexa-1,4,5-trien-1-ylbenzene (87639-20-1)

Guidance literature:

4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane; With C₅₇H₆₆N₂O₃S; sodium methylate; copper(l) chloride; In tetrahydrofuran; at 22 ℃; for 1.33333h; Inert atmosphere;

(E)-cinnamyl diethyl phosphate; In tetrahydrofuran; at 22 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja211269w

Reference yield:

4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0) + (E)-cinnamyl diethyl phosphate (85669-63-2) → (S)-3-phenyl-1,4,5-hexatriene (1353901-30-0) + (R,E)-4,4,5,5-tetramethyl-2-(4-phenylhexa-1,5-dien-1yl)-1,3,2-dioxaborolane

Guidance literature:

With C₅₇H₆₅N₂O₃S; copper(l) chloride; lithium tert-butoxide; In tetrahydrofuran; at 22 ℃; for 2h; Reagent/catalyst; enantioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.9b05465

Reference yield:

4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane (865350-17-0) + (E)-cinnamyl diethyl phosphate (85669-63-2) → (R)-3-phenyl-1,4,5-hexatriene (1353901-29-7) + (S)-3-phenyl-1,4,5-hexatriene (1353901-30-0) + (E)-hexa-1,4,5-trien-1-ylbenzene (87639-20-1)

Guidance literature:

With C₅₇H₆₆N₂O₃S; sodium methylate; copper(l) chloride; In tetrahydrofuran; at 22 ℃; for 0.4h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja211269w

upstream raw materials:

4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane

(E)-cinnamyl diethyl phosphate

Downstream raw materials:

(S,Z)-4,4,5,5-tetramethyl-2-(4-phenylhexa-2,5-dien-2-yl)-1,3,2-dioxaborolane

(S)-4-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,5-hexadiene