1. Synthesis and Structure of Tetrahydro-4,7-ethanoisobenzofuran-1,3-dione Derivative
- Author
-
Zhongxiang Lin, Chunmeng Pan, Guo-Yuan Lu, Mingfeng Fang, and Song Lu
- Subjects
NMR spectra database ,chemistry.chemical_compound ,Chemistry ,Stereochemistry ,Proton NMR ,Maleic anhydride ,General Chemistry ,DEPT ,Medicinal chemistry ,Single crystal ,Derivative (chemistry) ,Cycloaddition ,Adduct - Abstract
(1R,2R,3S,4R,7R)-7-Isopropyl-6-methylbicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid anhydride (tetrahydro-4,7-ethanoisobenzofuran-1,3-dione derivative) adduct 2 was prepared via the isomerization of α-pinene and β-pinene in turpentine followed by the Diels-Alder cycloaddition with maleic anhydride in the presence of phosphoric acid/iodine catalysis. The molecular structure of adduct 2 was characterized by IR, 1H NMR, 13C NMR, 1H-1H COSY, DEPT, HSQC, HMBC, 2D NOESY and MS spectra. The single crystal X-ray crystallographic analysis of adduct 2 was performed, and the X-ray powder diffractive spectrum of the sample adduct 2 is consistent with the diffractive spectrum calculated from the single crystal data. Therefore the structure and stereochemistry of adduct 2 was established based on extensive spectral data and single crystal X-ray analysis.
- Published
- 2015