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Unexpected synthesis and crystal structure of N-{2-[2-(2-acetyl-ethen-yl)phen-oxy]eth-yl}-N-ethenyl-4-methyl-benzene-sulfonamide.

ABSTRACT: The title compound, C₂₁H₂₃NO₄S, obtained by alkaline treatment of 1,5-bis-(1-phen-oxy)-3-aza-pentane at moderate heating, is a N-tosyl-ated secondary vinyl-amine. An intra-molecular S=O?H-C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential biological activities were performed, suggesting that the title compound can inhibit gluconate 2-de-hydrogenase (85% probability), as well as to act as a mucomembranous protector (73%).

SUBMITTER: Temesgen AW

PROVIDER: S-EPMC7784650 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Unexpected synthesis and crystal structure of N-{2-[2-(2-acetyl-ethen-yl)phen-oxy]eth-yl}-N-ethenyl-4-methyl-benzene-sulfonamide.

Temesgen Ayalew W AW Luong Minh Duc MD Truong Hong Hieu HH Nguyen Van Tuyen VT Dang Thi Tuyet Anh TTA Le Tuan Anh TA Tskhovrebov Alexander G AG Khrustalev Victor N VN

Acta crystallographica. Section E, Crystallographic communications 20201120 Pt 12

The title compound, C21H23NO4S, obtained by alkaline treatment of 1,5-bis-(1-phen-oxy)-3-aza-pentane at moderate heating, is a N-tosyl-ated secondary vinyl-amine. An intra-molecular S=O⋯H-C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential ...[more]

PMID: 33520267

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