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Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetra-hydro-1,3-benzodioxole-4,5-diol.

Macías MA, Suescun L, Pandolfi E, Schapiro V, Tibhe GD, Mombrú ÁW - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The dihedral angle between the mean planes of the rings is 76.80 (11)° as a result of their cis-fusion.In the crystal, mol-ecules are linked by two pairs of O-H⋯O hydrogen bonds, forming chains along [010].These chains are further connected by weaker C-H⋯O inter-actions along [100], creating (001) sheets that inter-act only by weak van der Waals forces.

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Affiliation: Cryssmat-Lab/Cátedra de Física/DETEMA, Facultad de Química, Universidad de la República, Montevideo, Uruguay ; Grupo INTERFASE, Universidad Industrial de Santander, Carrera 27, Calle 9, Ciudad Universitaria, Bucaramanga, Colombia.

ABSTRACT
The absolute configuration of the title compound, C10H16O4, determined as 3aS,4S,5R,7aR on the basis of the synthetic pathway, was confirmed by X-ray diffraction. The mol-ecule contains a five- and a six-membered ring that adopt twisted and envelope conformations, respectively. The dihedral angle between the mean planes of the rings is 76.80 (11)° as a result of their cis-fusion. In the crystal, mol-ecules are linked by two pairs of O-H⋯O hydrogen bonds, forming chains along [010]. These chains are further connected by weaker C-H⋯O inter-actions along [100], creating (001) sheets that inter-act only by weak van der Waals forces.

No MeSH data available.


Synthesis pathway and structural scheme of the chiral C10H16O4 compound.
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fig1: Synthesis pathway and structural scheme of the chiral C10H16O4 compound.

Mentions: Compounds containing an ep­oxy­cyclo­hexenone skeleton are very inter­esting, not only because of their wide spectrum of biological activities, but also because of their synthetically challenging chemical structures (Pandolfi et al., 2013 ▸). A biotransformation of toluene leads to a chiral diol (see Fig. 1 ▸) which is used as a precursor in enanti­oselective syntheses of ep­oxy­cyclo­hexenone compounds. Model compounds of the central core of ambuic acid (Labora et al., 2008 ▸), (+)- and (−)-bromoxone (Labora et al., 2010 ▸), an ep­oxy­quinol analog (Heguaburu et al., 2010 ▸), gabosine A, ent-epoformin and ent-epiepoformin (Labora et al., 2011 ▸) have been prepared starting from the same precursor. The title compound, diol (3) (see Fig. 1 ▸) has been prepared from iodo­hydrin (1), which, as indicated earlier, can be easily synthesized via biotransformation of toluene (Carrera et al., 2007 ▸).


Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetra-hydro-1,3-benzodioxole-4,5-diol.

Macías MA, Suescun L, Pandolfi E, Schapiro V, Tibhe GD, Mombrú ÁW - Acta Crystallogr E Crystallogr Commun (2015)

Synthesis pathway and structural scheme of the chiral C10H16O4 compound.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4555417&req=5

fig1: Synthesis pathway and structural scheme of the chiral C10H16O4 compound.
Mentions: Compounds containing an ep­oxy­cyclo­hexenone skeleton are very inter­esting, not only because of their wide spectrum of biological activities, but also because of their synthetically challenging chemical structures (Pandolfi et al., 2013 ▸). A biotransformation of toluene leads to a chiral diol (see Fig. 1 ▸) which is used as a precursor in enanti­oselective syntheses of ep­oxy­cyclo­hexenone compounds. Model compounds of the central core of ambuic acid (Labora et al., 2008 ▸), (+)- and (−)-bromoxone (Labora et al., 2010 ▸), an ep­oxy­quinol analog (Heguaburu et al., 2010 ▸), gabosine A, ent-epoformin and ent-epiepoformin (Labora et al., 2011 ▸) have been prepared starting from the same precursor. The title compound, diol (3) (see Fig. 1 ▸) has been prepared from iodo­hydrin (1), which, as indicated earlier, can be easily synthesized via biotransformation of toluene (Carrera et al., 2007 ▸).

Bottom Line: The dihedral angle between the mean planes of the rings is 76.80 (11)° as a result of their cis-fusion.In the crystal, mol-ecules are linked by two pairs of O-H⋯O hydrogen bonds, forming chains along [010].These chains are further connected by weaker C-H⋯O inter-actions along [100], creating (001) sheets that inter-act only by weak van der Waals forces.

View Article: PubMed Central - HTML - PubMed

Affiliation: Cryssmat-Lab/Cátedra de Física/DETEMA, Facultad de Química, Universidad de la República, Montevideo, Uruguay ; Grupo INTERFASE, Universidad Industrial de Santander, Carrera 27, Calle 9, Ciudad Universitaria, Bucaramanga, Colombia.

ABSTRACT
The absolute configuration of the title compound, C10H16O4, determined as 3aS,4S,5R,7aR on the basis of the synthetic pathway, was confirmed by X-ray diffraction. The mol-ecule contains a five- and a six-membered ring that adopt twisted and envelope conformations, respectively. The dihedral angle between the mean planes of the rings is 76.80 (11)° as a result of their cis-fusion. In the crystal, mol-ecules are linked by two pairs of O-H⋯O hydrogen bonds, forming chains along [010]. These chains are further connected by weaker C-H⋯O inter-actions along [100], creating (001) sheets that inter-act only by weak van der Waals forces.

No MeSH data available.