The title compound, C 17 H 18 N 2 O, was obtained by methylation of (4R,5R)-4,5-diphenylimidazolidin-2-one. The C-O bond exhibits double-bond character, and both C-N bonds in the urea group are intermediate between single and double bonds.
(S)-3-[(R)-2,4-Dimethylpent-4-enoyl]-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one
✍ Scribed by Tannert, René ;Schürmann, Markus ;Preut, Hans ;Arndt, Hans-Dieter ;Waldmann, Herbert
- Publisher
- International Union of Crystallography
- Year
- 2007
- Tongue
- English
- Weight
- 335 KB
- Volume
- 63
- Category
- Article
- ISSN
- 1600-5368
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✦ Synopsis
The title compound, C~25~H~29~NO~3~, was prepared in the course of the generation of depsipeptide libraries resembling the Jasplakinolide family of natural products. The dihedral angle between the phenyl ring planes is 74.1 (3)° The oxazolidinone ring adopts a slightly distorted ^4^
E conformation with an axial projection of the isopropyl substituent, which is easily rationalized by pseudo-allylic strain exerted by the exocyclic imide carbonyl. The two carbonyl groups adopt a noncolinear S-shaped conformation.
📜 SIMILAR VOLUMES
In the title compound, C 19 H 19 NO 3 , formed from enantiomerically pure (+)-(4R,5S)-4-methyl-5-phenyl-2-oxazolidinone and racemic 2-phenylpropanoyl chloride, the two carbonyl groups are oriented anti to each other, and the two methyl groups are oriented anti to each other.