(E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

Base Information

Chemical Name:(E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate
CAS No.:1374686-20-0
Molecular Formula:C₂₅H₃₁BO₆
Molecular Weight:438.329
Hs Code.:

Synonyms:(E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

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Chemical Property of (E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

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Technology Process of (E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

There total 3 articles about (E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate 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: 73.0%

: 1192068-13-5
dimethyl 2-(3-methylbuta-1,2-dienyl)-2-(3-phenylprop-2-ynyl)malonate

: 73183-34-3
bis(pinacol)diborane

: 1374686-20-0
(E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

Guidance literature:: With palladium diacetate; p-benzoquinone; In tetrahydrofuran; at 50 ℃; for 20h; regioselective reaction;
DOI:10.1002/anie.201107592

Reference yield:

: 1017595-73-1
dimethyl 2-(3-methylbuta-1,2-dienyl)-2-(prop-2-ynyl)malonate

: 1374686-20-0
(E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 25 °C

2: palladium diacetate; p-benzoquinone / tetrahydrofuran / 20 h / 50 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; N-ethyl-N,N-diisopropylamine; p-benzoquinone; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Sonogashira coupling;
DOI:10.1002/anie.201107592

Reference yield:

: 95124-07-5
dimethyl (prop-2-yn-1-yl)malonate

: 1374686-20-0
(E)-dimethyl 4-(phenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 - 25 °C

1.2: 20 h / Reflux

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 25 °C

3.1: palladium diacetate; p-benzoquinone / tetrahydrofuran / 20 h / 50 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; sodium hydride; N-ethyl-N,N-diisopropylamine; p-benzoquinone; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; 2.1: Sonogashira coupling;
DOI:10.1002/anie.201107592