(E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one

Base Information

• Chemical Name: (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one
• CAS No.: 1158715-34-4
• Molecular Formula: C₂₀H₂₉BO₃
• Molecular Weight: 328.259
• Mol file: 1158715-34-4.mol

Synonyms:(E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one

Chemical Property of (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one

There total 2 articles about (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-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: 85.0%

1-Phenylprop-1-yne (673-32-5) + 4-penten-3-one (1629-58-9) + bis(pinacol)diborane (73183-34-3) → (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one (1158715-34-4)

Guidance literature:

With catalyst: [Ni(1,5-cyclooctadiene)2]#(P(n-C₄H₉)3); In methanol; toluene; toluene/CH3OH (3:1); flask with Ni and diboron compds. evacuated and purged with N2 3 times, added toluene and P(C4H9)3, stirred, added enone, alkyne and CH3OH, stirred at room temp. for 5 min and then at 40°Cfor 10 h; filtered through short pad of celite and washed with ethyl acetate/hexane (70:30 v/v), filtrate concd., residue purified by column chromy. on silica gel with hexanes-ethyl acetate as eluent;

DOI:10.1002/anie.200805293

Reference yield: 50.0%

1-Phenylprop-1-yne (673-32-5) + 4-penten-3-one (1629-58-9) + bis(pinacol)diborane (73183-34-3) → (E)-6-methyl-7-phenylhept-6-en-3-one + (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one (1158715-34-4)

Guidance literature:

With methanol; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tributylphosphine; Inert atmosphere;

DOI:10.1002/anie.200805293

Reference yield: 89.0%

iodobenzene (591-50-4) + (E)-6-methyl-7-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one (1158715-34-4) → 6-methyl-7,7-diphenylhept-6-en-3-one (1158715-98-0)

Guidance literature:

With potassium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; water; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.200805293

upstream raw materials:

1-Phenylprop-1-yne

4-penten-3-one

bis(pinacol)diborane

Downstream raw materials:

(Z)-6-methyl-7-(4-nitrophenyl)-7-phenylhept-6-en-3-one

2-methyl-1-phenylheptane-1,5-dione

6-methyl-7,7-diphenylhept-6-en-3-one