Art

J-GLOBAL ID：202002213736632628   Reference number：20A0539981

SELECTIVE AROMATIC NUCLEOPHILIC SUBSTITUTION OF 4-DIMETHYLAMINO-2-METHOXY-3-(TRIFLUOROACETYL)QUINOLINE WITH ALCOHOLS-DFT CALCULATION STUDY

アルコールによる4-ジメチルアミノ-2-メトキシ-3-(トリフルオロアセチル)キノリンの選択的芳香族求核置換:DFT計算研究

Author (4)： OTA Norio (Kobe Univ., Kobe, JPN) ,  HARADA Yusuke (Kobe Univ., Kobe, JPN) ,  KAMITORI Yasuhiro (Kobe Univ., Kobe, JPN) ,  OKADA Etsuji (Kobe Univ., Kobe, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 101  Issue： 2  Page： 692-700  Publication year： Jan. 01, 2020 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *density functional method ,  *nucleophilic substitution reaction ,  nitrogen heterocyclic compound ,  polynuclear aromatic compound ,  anion ,  complex (compound) ,  reaction intermediate ,  protonation ,  aliphatic alcohol ,  alcoholysis ,  aminolysis ,  HOMO ,  LUMO ,  thiol ,  primary amine ,  regiospecific reaction ,  acyl group ,  Meisenheimer complex ,  trifluoroacetyl group ,  Quinolines ,  *nucleophilic aromatic substitution ,  aliphatic amine
Semi thesaurus term： B3LYP ,  *DFT calculation ,  alcoholysis ,  quinoline derivative ,  *nucleophilic aromatic substitution reaction

JST classification (3)： Substitution reaction  (CF02020B) ,  Quinolines,isoquinolines  (CF07096H) ,  Electronic structure of molecules  (BH05010Q)

Substance index (14)： 1-(2-Methoxy-4-butoxy-3-quinolyl)-2,2,2-trifluoroethanone ,  1-(2-Butylamino-4-dimethylamino-3-quinolinyl)-2,2,2-trifluoroethanone ,  1-[2-(butylsulfanyl)-4-(dimethylamino)quinolin-3-yl]-2,2,2-trifluoroethanone ,  1-[2-butoxy-4-(dimethylamino)-2-methoxy-1H-quinolin-3-yl]-2,2,2-trifluoroethanone ,  1-[2-butoxy-4-(dimethylamino)quinolin-3-yl]-2,2,2-trifluoroethanone ,  1-[2-butoxy-4-(dimethylamino)-2-methoxyquinolin-3-ylidene]-2,2,2-trifluoroethanol ,  2-Methoxy-3-(trifluoroacetyl)-4-(dimethylamino)quinoline ,  1-[2-Methoxy-4-(phenethyloxy)-3-quinolyl]-2,2,2-trifluoroethanone ,  N-Butyl-2-methoxy-3-(trifluoroacetyl)quinoline-4-amine ,  [2-Methoxy-4-(butylthio)-3-quinolyl](trifluoromethyl) ketone ,  1-[4-butoxy-4-(dimethylamino)-2-methoxyquinolin-3-ylidene]-2,2,2-trifluoroethanol ,  1-[4-butoxy-4-(dimethylamino)-2-methoxy-1H-quinolin-3-yl]-2,2,2-trifluoroethanone ,  Butylamine ,  1-Butanol

Reference (14)：

• R. Filler and Y. Kobayashi, ‘Biomedicinal Aspects of Fluorine Chemistry', Kodansha & Elsevier Biomedical, Tokyo, 1982.
• R. Filler, ‘Organofluorine Chemicals and Their Industrial Applications', ed. by R. E. Banks, Ellis Horwood, Ltd., London, 1979.
• J. T. Welch, Tetrahedron, 1987, 43, 3123.
• R. Filler, Y. Kobayashi, and L. M. Yagupolskii, ‘Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications', Elsevier, Amsterdam, 1993.
• M. Hatakenaka, S. Adachi, and E. Okada, Heterocycles, 2016, 92, 936.

Terms in the title (5)： アルコール ,  キノリン ,  芳香族求核置換 ,  DFT計算 ,  研究