(E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

Base Information

Chemical Name:(E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate
CAS No.:1620683-10-4
Molecular Formula:C₁₆H₂₀F₃NO₂
Molecular Weight:315.336
Hs Code.:

Synonyms:(E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

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Chemical Property of (E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

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Technology Process of (E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

There total 4 articles about (E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate 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: 75.0%

: 402-43-7
p-trifluoromethylphenyl bromide

: 169268-90-0
3-N-tert-butoxycarbonylamino-N-methyl-1-propene

: 1620683-10-4
(E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

Guidance literature:: 3-N-tert-butoxycarbonylamino-N-methyl-1-propene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

p-trifluoromethylphenyl bromide; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 60 ℃; for 15h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol5018257

Reference yield: 35.0%

: 402-43-7
p-trifluoromethylphenyl bromide

: 169268-90-0
3-N-tert-butoxycarbonylamino-N-methyl-1-propene

: 1620683-10-4
(E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

: 1620683-11-5
(Z)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

Guidance literature:: 3-N-tert-butoxycarbonylamino-N-methyl-1-propene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

p-trifluoromethylphenyl bromide; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 60 ℃; for 15h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol5018257

Reference yield:

: 78888-18-3
N-tert-butoxycarbonylprop-2-en-1-amine

: 1620683-10-4
(E)-tert-butyl methyl(3-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 15 h / 60 °C / Inert atmosphere

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; mineral oil; 2.3: |Negishi Coupling;
DOI:10.1021/ol5018257