Synthesis, crystal structure and absolute configuration of (3a<i>S</i>,4<i>R</i>,5<i>S</i>,7a<i>R</i>)-7-(but-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2<i>H</i>-1,3-benzodioxole-4,5-diol

The absolute configuration of the title compound, C<sub>13</sub>H<sub>16</sub>O<sub>4</sub>, determined as 1<i>S</i>,2<i>R</i>,3<i>S</i>,4<i>R</i> based on the synthetic pathway, was confirmed by single-crystal X-ray diffraction. The mol-ecule is a relevant inter-mediary for the synthesis of speciosins, ep-oxy-quinoides or their analogues. The mol-ecule contains fused five- and six-membered rings with two free hydroxyl groups and two protected as an iso-propyl-idenedioxo ring. The packing is directed by hydrogen bonds that define double planes of mol-ecules laying along the <i>ab</i> plane and van der Waals inter-actions between aliphatic chains that point outwards of the planes.

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Publication Details

Journal
Acta Crystallographica Section E Crystallographic Communications
Published
2024-10-11
DOI
https://doi.org/10.1107/s2056989024009733
Primary Topic
Plant Toxicity and Pharmacological Properties
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis, crystal structure and absolute configuration of (3aS,4R,5S,7aR)-7-(but-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2H-1,3-benzodioxole-4,5-diol

Leopoldo Suescun, Alejandro Peixoto de Abreu Lima, Valeria Schapiro, Enrique Pandolfi
Acta Crystallographica Section E Crystallographic Communications
Plant Toxicity and Pharmacological Properties
article

Synthesis, crystal structure and absolute configuration of (3aS,4R,5S,7aR)-7-(but-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2H-1,3-benzodioxole-4,5-diol

Leopoldo Suescun, Alejandro Peixoto de Abreu Lima, Valeria Schapiro, Enrique Pandolfi
article en

Abstract

The absolute configuration of the title compound, C<sub>13</sub>H<sub>16</sub>O<sub>4</sub>, determined as 1<i>S</i>,2<i>R</i>,3<i>S</i>,4<i>R</i> based on the synthetic pathway, was confirmed by single-crystal X-ray diffraction. The mol-ecule is a relevant inter-mediary for the synthesis of speciosins, ep-oxy-quinoides or their analogues. The mol-ecule contains fused five- and six-membered rings with two free hydroxyl groups and two protected as an iso-propyl-idenedioxo ring. The packing is directed by hydrogen bonds that define double planes of mol-ecules laying along the <i>ab</i> plane and van der Waals inter-actions between aliphatic chains that point outwards of the planes.

Acta Crystallographica Section E Crystallographic CommunicationsVol. 80(11)
Universidad de la República de Uruguay (UY), Instituto de Química Orgánica General (ES), Centro Uruguayo de Imagenología Molecular (UY)
Agencia Nacional de Investigación e Innovación, Universidad de la República Uruguay
Clean water and sanitation
Openalex Percentile: Top 84%
Plant Toxicity and Pharmacological Properties
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