methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate

Base Information

• Chemical Name: methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate
• CAS No.: 121712-61-6
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.263
• Mol file: 121712-61-6.mol

Synonyms:

Chemical Property of methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate

There total 1 articles about methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate 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: 57.0%

N-methoxy-N-methylcinnamamide (80783-99-9,124931-15-3,113474-86-5) + acetoacetic acid methyl ester (105-45-3) → methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate (121712-61-6)

Guidance literature:

With n-butyllithium; sodium hydride; 1) THF, 0 deg C, 10 min, 2) -10 deg C, 10 min, hexane, 3) -78 to -30 deg C, 30 min; method for preparation of β,γ-diketo esters. Coupling with other electrophiles gave poor results.;

DOI:10.1016/S0040-4039(00)82375-8

Reference yield: 86.0%

methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate (121712-61-6) → methyl (E,3S*,5R*)-3,5-dihydroxy-7-phenyl-6-heptenoate (103338-09-6,107400-63-5,109486-16-0,110454-39-2,110454-42-7,111136-40-4,118845-65-1,121786-82-1,125517-61-5,142033-86-1,149115-61-7,150576-63-9)

Guidance literature:

With sodium tetrahydroborate; diethyl methoxy borane; Mechanism; 1) THF, methanol, -78 deg C to r.t., 2) -78 deg C to r.t.; method for stereoselective reduction to syn-β,γ-dihydroxy esters. By using chiral dialkyl(methoxy)borane reduction with low enantioselectivity was feasible.;

DOI:10.1016/S0040-4039(00)82375-8

Reference yield:

methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate (121712-61-6) → methyl (E,3S*,5R*)-3,5-dihydroxy-7-phenyl-6-heptenoate (103338-09-6,107400-63-5,109486-16-0,110454-39-2,110454-42-7,111136-40-4,118845-65-1,121786-82-1,125517-61-5,142033-86-1,149115-61-7,150576-63-9) + methyl (+/-)-(3R*,5R*,6E)-3,5-dihydroxy-7-phenyl-6-heptanoate (103338-09-6,107400-63-5,109486-16-0,110454-39-2,110454-42-7,111136-40-4,118845-65-1,121786-82-1,125517-61-5,142033-86-1,149115-61-7,150576-63-9)

Guidance literature:

With methanol; sodium tetrahydroborate; diethyl methoxy borane; Yield given. Multistep reaction;

DOI:10.1246/bcsj.68.350

upstream raw materials:

N-methoxy-N-methylcinnamamide

acetoacetic acid methyl ester

Downstream raw materials:

methyl (E,3S^*,5R^*)-3,5-dihydroxy-7-phenyl-6-heptenoate

methyl (+/-)-(3R*,5R*,6E)-3,5-dihydroxy-7-phenyl-6-heptanoate