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(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole

The mol­ecule of the title compound, C(16)H(21)BO(2), comprises a chiral fused tricyclic system containing five-membered (1,3,2-dioxaborolane), six-membered (cyclo­hexa­ne) and four-membered (cyclo­butane) rings. The 1,3,2-dioxaborolane ring is almost planar (r.m.s. deviation = 0.035 Å), and the syn...

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Autores principales: Lejon, Tore, Gozhina, Olga V., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515203/
https://www.ncbi.nlm.nih.gov/pubmed/23284430
http://dx.doi.org/10.1107/S1600536812041712
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author Lejon, Tore
Gozhina, Olga V.
Khrustalev, Victor N.
author_facet Lejon, Tore
Gozhina, Olga V.
Khrustalev, Victor N.
author_sort Lejon, Tore
collection PubMed
description The mol­ecule of the title compound, C(16)H(21)BO(2), comprises a chiral fused tricyclic system containing five-membered (1,3,2-dioxaborolane), six-membered (cyclo­hexa­ne) and four-membered (cyclo­butane) rings. The 1,3,2-dioxaborolane ring is almost planar (r.m.s. deviation = 0.035 Å), and the syn H and Me substituents at this ring are in an eclipsed conformation. The cyclo­hexane and cyclo­butane rings adopt sofa and butterfly conformations, respectively. The B atom has a trigonal–planar configuration (sum of the bond angles = 360.0°). The phenyl ring is practically coplanar with the 1,3,2-dioxaborolane ring [dihedral angle between the ring planes = 1.96 (8)°]. The absolute structure was determined from the known configuration of (+)-pinanediol which was used in the synthesis. In the crystal, weak C—H⋯π(Ph) inter­actions occur.
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spelling pubmed-35152032013-01-02 (3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole Lejon, Tore Gozhina, Olga V. Khrustalev, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The mol­ecule of the title compound, C(16)H(21)BO(2), comprises a chiral fused tricyclic system containing five-membered (1,3,2-dioxaborolane), six-membered (cyclo­hexa­ne) and four-membered (cyclo­butane) rings. The 1,3,2-dioxaborolane ring is almost planar (r.m.s. deviation = 0.035 Å), and the syn H and Me substituents at this ring are in an eclipsed conformation. The cyclo­hexane and cyclo­butane rings adopt sofa and butterfly conformations, respectively. The B atom has a trigonal–planar configuration (sum of the bond angles = 360.0°). The phenyl ring is practically coplanar with the 1,3,2-dioxaborolane ring [dihedral angle between the ring planes = 1.96 (8)°]. The absolute structure was determined from the known configuration of (+)-pinanediol which was used in the synthesis. In the crystal, weak C—H⋯π(Ph) inter­actions occur. International Union of Crystallography 2012-10-13 /pmc/articles/PMC3515203/ /pubmed/23284430 http://dx.doi.org/10.1107/S1600536812041712 Text en © Lejon et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Lejon, Tore
Gozhina, Olga V.
Khrustalev, Victor N.
(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
title (3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
title_full (3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
title_fullStr (3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
title_full_unstemmed (3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
title_short (3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
title_sort (3as,4s,6s,7ar)-hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515203/
https://www.ncbi.nlm.nih.gov/pubmed/23284430
http://dx.doi.org/10.1107/S1600536812041712
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