X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one

被引：1

作者：

Choi, Seunghyun ^{[1
]}

Kim, YunHye ^{[1
]}

Park, Bernie Byeonghoon ^{[1
]}

Park, Suzie ^{[1
]}

Park, Jonghyun ^{[1
]}

Ok, Kiwon ^{[1
]}

Koo, JaeHyung ^{[2
]}

Jung, Yong Woo ^{[1
]}

Jeon, Young Ho ^{[1
]}

Lee, Eun Hee ^{[1
]}

Lee, Ken S. ^{[3
]}

Byun, Youngjoo ^{[1
,4
]}

机构：

[1] Korea Univ, Coll Pharm, Sejong 339700, South Korea

[2] Daegu Gyeongbuk Inst Sci & Technol, Dept Brain Sci, Taegu 711873, South Korea

[3] Jackson State Univ, Dept Chem & Biochem, Jackson, MS 39217 USA

[4] Korea Univ, Guro Hosp, Biomed Res Ctr, Seoul 152703, South Korea

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2014年 / 1076卷

基金：

新加坡国家研究基金会;

关键词：

Enaminones; X-ray diffraction; VT-NMR; Flexible rotation; ENAMINONES; BENZOYLACETONE; CONDENSATION; TAUTOMERISM; DERIVATIVES; PRODUCTS;

D O I：

10.1016/j.molstruc.2014.08.016

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of 1-aryl-3-(cyclicamino)-prop-2-en-1-one analogs was synthesized from commercial acetophenones in 2 or 3 steps. Compound 6, (E)-3-(piperidinyl)-1-(2'-hydroxyphenyl)-prop-2-en-1-one, exhibited the unique shape and intensity of the C-sp2-N-CH2 peaks in the H-1 and C-13 NMR spectra. Variable temperature (VT) nuclear magnetic resonance (NMR) and X-ray diffraction (XRD) studies of 6 revealed that the piperidine ring has a lower energy barrier to rotation than the 5-membered pyrrolidine 9 due to the less effective pi electron delocalization along the C-sp2-N bond. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：600 / 605

页数：6

共 17 条

[1] SYNTHESIS AND STRUCTURE ACTIVITY RELATIONSHIPS OF NOVEL ARYLFLUOROQUINOLONE ANTIBACTERIAL AGENTS
CHU, DTW
FERNANDES, PB
CLAIBORNE, AK
PIHULEAC, E
NORDEEN, CW
MALECZKA, RE
PERNET, AG
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (11) : 1558 - 1564
[2] Microwave-assisted synthesis of some new pyrazolopyridines and their antioxidant, antitumor and antimicrobial activities
El-Borai, Mohamed A.
Rizk, Hala F.
Beltagy, Doha M.
El-Deeb, Ibrahim Y.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 : 415 - 422
[3] Synthesis of Chromone, Quinolone, and Benzoxazinone Sulfonamide Nucleosides as Conformationally Constrained Inhibitors of Adenylating Enzymes Required for Siderophore Biosynthesis
Engelhart, Curtis A.
Aldrich, Courtney C.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15) : 7470 - 7481
[4] Hamdy NA, 2013, ACTA POL PHARM, V70, P99
[5] Unambiguous structure elucidation of heterocyclic products from condensation-cyclisation reactions of enaminones by 2D INADEQUATE and 15N NMR
Liermann, Johannes C.
Elnagdi, Mohamed Hilmy
Meier, Herbert
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 2013, 51 (01) : 16 - 18
[6] Okoro CO, 2013, LETT DRUG DES DISCOV, V10, P1024
[7] Multicomponent Synthesis of Antibacterial Dihydropyridin and Dihydropyran Embelin Derivatives
Pena, Rosalyn
Jimenez-Alonso, Sandra
Feresin, Gabriela
Tapia, Alejandro
Mendez-Alvarez, Sebastian
Machin, Felix
Ravelo, Angel G.
Estevez-Braun, Ana
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) : 7977 - 7985
[8] 1-aryl-3-(dimethylamino)propenones: Strong proton acceptors for hydrogen bonds
Pleier, AK
Herdtweck, E
Mason, SA
Thiel, WR
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (03) : 499 - 506
[9] Preparation of Polysubstituted Isochromanes by Addition of ortho-Lithiated Aryloxiranes to Enaminones
Salomone, Antonio
Perna, Filippo Maria
Sassone, Francesca Claudia
Falcicchio, Aurelia
Bezensek, Jure
Svete, Jurij
Stanovnik, Branko
Florio, Saverio
Capriati, Vito
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) : 11059 - 11065
[10] Bis-Enaminones as versatile precursors for terheterocycles: synthesis and reactions
Shawali, Ahmad Sami
[J]. ARKIVOC, 2012, : 383 - 431

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