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
Alejandro Peixoto de Abreu Lima , Enrique Pandolfi , Valeria Schapiro , Leopoldo Suescun
{"title":"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","authors":"Alejandro Peixoto de Abreu Lima , Enrique Pandolfi , Valeria Schapiro , Leopoldo Suescun","doi":"10.1107/S2056989024009733","DOIUrl":null,"url":null,"abstract":"<div><div>The crystal structure of the title compound was solved to confirm the relative absolute configuration of the chiral centers.</div></div><div><div>The absolute configuration of the title compound, C<sub>13</sub>H<sub>16</sub>O<sub>4</sub>, determined as 1<em>S</em>,2<em>R</em>,3<em>S</em>,4<em>R</em> based on the synthetic pathway, was confirmed by single-crystal X-ray diffraction. The molecule is a relevant intermediary for the synthesis of speciosins, epoxyquinoides or their analogues. The molecule contains fused five- and six-membered rings with two free hydroxyl groups and two protected as an isopropylidenedioxo ring. The packing is directed by hydrogen bonds that define double planes of molecules laying along the <em>ab</em> plane and van der Waals interactions between aliphatic chains that point outwards of the planes.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"80 11","pages":"Pages 1165-1169"},"PeriodicalIF":0.5000,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11660465/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section E: Crystallographic Communications","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2056989024002470","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}
引用次数: 0
Abstract
The crystal structure of the title compound was solved to confirm the relative absolute configuration of the chiral centers.
The absolute configuration of the title compound, C13H16O4, determined as 1S,2R,3S,4R based on the synthetic pathway, was confirmed by single-crystal X-ray diffraction. The molecule is a relevant intermediary for the synthesis of speciosins, epoxyquinoides or their analogues. The molecule contains fused five- and six-membered rings with two free hydroxyl groups and two protected as an isopropylidenedioxo ring. The packing is directed by hydrogen bonds that define double planes of molecules laying along the ab plane and van der Waals interactions between aliphatic chains that point outwards of the planes.
期刊介绍:
Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.