Crystal structure and computational study of 3,4-dihydroxy-3-hydroxymethyl-9-methyl-6-methylidene-3a,4,5,6,6a,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8(3H,7H)-dione
نویسندگان
چکیده
In the mol-ecule of title compound, C15H20O6, also known as cynarinin A, the cyclo-pentane ring having twist conformation and a γ-lactone ring assuming an envelope conformation are trans- and cis-fused, respectively, to a cyclo-heptane ring adopting a twist-chair conformation. In the crystal, O-H⋯O hydrogen bonds link neighbouring mol-ecules, forming a three-dimensional network. Theoretical calculations of the mol-ecular structure using the CNDO approximation and MOPAC PM3 geometry optimization are in satisfactory agreement with the results of the X-ray structure analysis.
منابع مشابه
5,9-Dihydroxy-9-methyl-3,6-dimethylene-3a,4,5,6,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2(3H)-one
The title compound, C(15)H(20)O(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle...
متن کاملA dimeric sesquiterpene, gochnatiolide A
THE TITLE COMPOUND [SYSTEMATIC NAME: 5'a-hydroxy-1',3,6,8'-tetrakis(methylene)-3a,4,5,5',5'a,6,6',6a,7,7',7'a,8',9a,9b,10'a,10'b-hexadecahydrospiro[azuleno[4,5-b]furan-9(2H),3'-[3H]benz[1,8]azuleno[4,5-b]furan]-2,2',8,9'(1'H,3H,4'H)-tetrone acetone 0.92-solvate], C(30)H(30)O(7)·0.92C(3)H(6)O, is a dimeric sequiterpene formed by a cyclohexane system connecting two monomeric sesquiterpene lactone...
متن کامل5-Benzyl-7-methylhexahydro-3a,7-methano-1H-furo[3,4-c]azocine-3,10(4H)-dione
The title compound, C(18)H(21)NO(3), was obtained via a double Mannich condensation reaction of 6-methyl-tetra-hydro-isobenzofuran-1,7(3H,7aH)-dione with formaldehyde and benzyl-amine. The mol-ecule contains three fused rings of which the cyclo-hexa-none and piperidine rings adopt chair conformations and the furan-one ring assumes an envelope conformation. An inter-molecular C-H⋯π inter-action ...
متن کامل1-Methyl-7-(4-nitrophenyl)-3-phenylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione
In the title compound, C(21)H(13)N(5)O(4), the dihedral angles formed between the planes of the phenyl and nitro-phenyl rings and that of the heterotricyclic plane are 41.29 (7) and 61.35 (6)°, respectively. In the crystal, weak C-H⋯O interactions help to establish the packing.
متن کاملfuran-2(3H),1′-[2]cyclohexene]-3,4′-dione IUPAC Systematic Name: 7-Chloro-2′,4,6-trimethoxy-6′β-methylspiro[benzo- furan-2(3H),1′-[2]cyclohexene]-3,4′-dione Synonyms: (2S,4′R)-7-Chloro-2′,4,6-trimethoxy-4′-methylspiro[benzofuran-2- (3H),3′-cyclohexene]-3,6′-dione; (1′S-trans)-7-chloro-2′,4,6-trimethoxy-6′-methyl- spiro[benzofuran-2(3H),1′-[2]cyclohexene]-3,4′-dione; (+)-griseofulvin; (+)-7- chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1′-(2′-methoxy-6′-methylcyclohex-
Chem. Abstr. Serv. Reg. No.: 126-07-8 Deleted CAS Nos: 8027-03-0; 8055-10-5; 3426-54-8; 11103-62-1; 24659-79-8 Chem. Abstr. Name: (1′S,6′R)-7-Chloro-2′,4,6-trimethoxy-6′-methylspiro[benzofuran-2(3H),1′-[2]cyclohexene]-3,4′-dione IUPAC Systematic Name: 7-Chloro-2′,4,6-trimethoxy-6′β-methylspiro[benzofuran-2(3H),1′-[2]cyclohexene]-3,4′-dione Synonyms: (2S,4′R)-7-Chloro-2′,4,6-trimethoxy-4′-methyl...
متن کامل