Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate

Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate

A Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-pheny...

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Bibliographic Details
Main Author: Sung-Gon Kim
Format: Article
Language:English
Published: MDPI AG 2017-03-01
Series:Molbank
Subjects:
tetralin
Friedel-Crafts reaction
Michael addition
cascade reaction
Online Access:http://www.mdpi.com/1422-8599/2017/1/M933
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spelling doaj-234632a8b7a2495aa77ea0509c46b8f22020-11-24T20:56:02ZengMDPI AGMolbank1422-85992017-03-0120171M93310.3390/M933M933Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylateSung-Gon Kim0Department of Chemistry, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, KoreaA Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate. This reaction provided diastereoslective trans tetralin (7:3 dr) on the cyclohexyl ring. The structure of the newly synthesized compound was determined using 1H-, 13C-NMR, IR and mass spectral data.http://www.mdpi.com/1422-8599/2017/1/M933tetralinFriedel-Crafts reactionMichael additioncascade reaction
collection DOAJ
language English
format Article
sources DOAJ
author Sung-Gon Kim
spellingShingle Sung-Gon Kim
Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
Molbank
tetralin
Friedel-Crafts reaction
Michael addition
cascade reaction
author_facet Sung-Gon Kim
author_sort Sung-Gon Kim
title Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
title_short Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
title_full Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
title_fullStr Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
title_full_unstemmed Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
title_sort dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1h)-dicarboxylate
publisher MDPI AG
series Molbank
issn 1422-8599
publishDate 2017-03-01
description A Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate. This reaction provided diastereoslective trans tetralin (7:3 dr) on the cyclohexyl ring. The structure of the newly synthesized compound was determined using 1H-, 13C-NMR, IR and mass spectral data.
topic tetralin
Friedel-Crafts reaction
Michael addition
cascade reaction
url http://www.mdpi.com/1422-8599/2017/1/M933
work_keys_str_mv AT sunggonkim dimethyl7dimethylamino34dihydro12oxopropyl4phenylnaphthalene221hdicarboxylate
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