(5aS,8R,9aR)-5,5,8-Trimethyloctahydrobenzo[f][1,4]oxazepin-3(2H)-one

(5aS,8R,9aR)-5,5,8-Trimethyloctahydrobenzo[f][1,4]oxazepin-3(2H)-one Full article

Journal

MolBank
ISSN: 1422-8599

Output data

Year: 2026, Volume: 2026, Number: 5, Article number : M2225, Pages count : DOI: 10.3390/m2225

Tags

monoterpenoids; isopulegol; 1,4-oxazepan-3-one; intramolecular cyclization

Authors

Li-Zhulanov Nikolai S. ¹ , Golovchenko Dmitrii D. ^1,2 , Rybalova Tatyana V. ¹ , Modelskaya Maria E. ^1,3 , Rogachev Artem D. ^1,3 , Volcho Konstantin P. ¹ , Salakhutdinov Nariman F. ¹

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentiev Avenue 9, 630090 Novosibirsk, Russia
2	Department of Natural Sciences, Novosibirsk State University, Pirogov Str., 1, 630090 Novosibirsk, Russia
3	Institute of Medicine and Medical Technologies, Novosibirsk State University, Pirogov Str., 1, 630090 Novosibirsk, Russia

Funding (1)

Российский Научный Фонд

25-23-01218

The monoterpene-derived 1,4-oxazepan-3-one, (5aS,8R,9aR)-5,5,8-trimethyloctahydrobenzo[f][1,4]oxazepin-3(2H)-one, was synthesized from the corresponding (−)-isopulegol-based chloroacetamide by intramolecular cyclization in acetonitrile. The product was isolated in 70% yield as colorless crystals. Its structure was established by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry and was confirmed by single-crystal X-ray diffraction analysis. The transformation provides concise access to a fused bicyclic 1,4-oxazepan-3-one bearing a stereochemically defined para-menthane scaffold.

Li-Zhulanov N.S. , Golovchenko D.D. , Rybalova T.V. , Modelskaya M.E. , Rogachev A.D. , Volcho K.P. , Salakhutdinov N.F.
(5aS,8R,9aR)-5,5,8-Trimethyloctahydrobenzo[f][1,4]oxazepin-3(2H)-one
MolBank. 2026. V.2026. N5. M2225 . DOI: 10.3390/m2225 OpenAlex

Submitted:	Jul 31, 2026
Accepted:	Aug 31, 2026
Published online:	Sep 1, 2026

≡ OpenAlex:

W7204914514