methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate

Base Information

• Chemical Name: methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate
• CAS No.: 910132-85-3
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• Mol file: 910132-85-3.mol

Synonyms:methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate

Chemical Property of methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate

There total 8 articles about methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate 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: 94.0%

methyl 3,5-dimethyl-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (341006-48-2) + tert-Butyl acrylate (1663-39-4,25232-27-3) → methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate (910132-85-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium iodide; triethylamine; In N,N-dimethyl-formamide; at 110 ℃; for 0.833333h; microwave irradiation;

DOI:10.1021/jm060369k

Reference yield: 68.0%

tert-Butyl acrylate (1663-39-4,25232-27-3) + methyl 4-iodo-3-methylbenzoate (5471-81-8) + methyl p-toluene sulfonate (80-48-8) → methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate (910132-85-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; 5-norbornene-2-carbonitrile; caesium carbonate; In acetonitrile; at 80 ℃; for 15h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.9b07857

Reference yield: 67.0%

tert-Butyl acrylate (1663-39-4,25232-27-3) + 4-methoxycarbonylphenyl bromide (619-42-1) + methyl p-toluene sulfonate (80-48-8) → methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-3,5-dimethylbenzoate (910132-85-3)

Guidance literature:

With norborn-2-ene; trifuran-2-yl-phosphane; palladium diacetate; caesium carbonate; In 1,4-dioxane; for 15h; Inert atmosphere; Schlenk technique; Heating;

DOI:10.1021/jacs.9b07857

upstream raw materials:

methyl 3,5-dimethyl-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate

tert-Butyl acrylate

2.6-dimethylphenol

4-iodo-2,6-dimethylphenol

Downstream raw materials:

tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid

tert-butyl (E)-3-(2,6-dimethyl-4-carbamoylphenyl)acrylate

Refernces

• 1、 Lu, Yixin,Lum, Tze Keong,Augustine, Yoon Wui Leow,Weltrowska, Grazyna,Nguyen, Thi M.-D.,Lemieux, Carole,Chung, Nga N.,Schiller, Peter W.. "Replacement of the N-terminal tyrosine residue in opioid peptides with 3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid (Dcp) results in novel opioid antagonists". . p. 5382 - 5385. Retrieved 2007/10/03.