Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(2aR,5S,6aS,8aS,E)-Ethyl 5-hy-droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa-hydro-1H-penta-leno[1,6-bc]oxepine-4-carboxyl-ate.

ABSTRACT: The title compound, C17H24O5, featuring a 2-carbeth-oxy-3-oxepanone unit in its intra-molecularly O-H⋯O hydrogen-bonded enol form, was obtained via [(CF3CO2)2Rh]2-catal-ysed intra-molecular O-H bond insertion in the α-diazo-ω-hy-droxy-β-ketoester, ethyl 4-[(1S,3aS,6R,6aS)-6-hy-droxy-2,2,3a-trimethyl-3-oxo-octa-hydro-penta-len-1-yl]-2-diazo-3-oxobutano-ate. The seven-membered oxacyclic ring, thus constructed on a cis-fused diquinane platform, was found to adopt a distorted boat-sofa conformation.

SUBMITTER: Mehta G

PROVIDER: S-EPMC3588985 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(2aR,5S,6aS,8aS,E)-Ethyl 5-hy-droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa-hydro-1H-penta-leno[1,6-bc]oxepine-4-carboxyl-ate.

Mehta Goverdhan G Kumar C S Ananda CS Sen Saikat S

Acta crystallographica. Section E, Structure reports online 20121124 Pt 12

The title compound, C17H24O5, featuring a 2-carbeth-oxy-3-oxepanone unit in its intra-molecularly O-H⋯O hydrogen-bonded enol form, was obtained via [(CF3CO2)2Rh]2-catal-ysed intra-molecular O-H bond insertion in the α-diazo-ω-hy-droxy-β-ketoester, ethyl 4-[(1S,3aS,6R,6aS)-6-hy-droxy-2,2,3a-trimethyl-3-oxo-octa-hydro-penta-len-1-yl]-2-diazo-3-oxobutano-ate. The seven-membered oxacyclic ring, thus constructed on a cis-fused diquinane platform, was found to adopt a distorted boat-sofa conformation. ...[more]

PMID: 23476221

Similar Datasets

(8aS)-7,8,8a,9-Tetra-hydro-thieno[3,2-f]indolizin-6(4H)-one.

Project description:In the mol-ecular structure of the title compound, C(10)H(11)NOS, the central six-membered ring of the indolizine unit adopts an envelope conformation, the maximum deviations from the mean plane of the ring being 0.533 (2) Å. The fused thieno ring is nearly coplanar [mean deviation = 0.007 (2) Å]. The conformation of the fused oxopyrrolidine ring is close to that of a flat-envelope, with a maximum deviation of 0.339 (3) Å. The crystal structure is stabilized by C-H⋯O hydrogen bonds.

| S-EPMC2968850 | biostudies-literature

Ethyl (4aR*,7S*,8S*,8aS*)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexa-hydro-1H-isochromene-8-carboxyl-ate.

Project description:In the title compound, C(18)H(20)O(4), both the tetra-hydro-pyran-one ring and the cyclo-hexene ring adopt envelope conformations. The crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen bonding.

| S-EPMC2979652 | biostudies-literature

(4aR,6aS,10aR,10bS)-7,7,10a-Trimethyl-1,4,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-2H-naphtho-[2,1-c]pyran (Pyamber).

Project description:The crystal structure of the title compound, C(16)H(28)O, features C-H⋯O hydrogen bonds making C(6) zigzag chains along one 2(1) screw axis. Within the limits of the data collection affected by crystal quality, the Hooft parameter gave correct indications of the known molecular chirality based on the single O atom anomalous dispersion in contrast to the indeterminate Flack value. Synthetic steps starting from manool are reported.

| S-EPMC3247605 | biostudies-literature

(±)-(4bS,8aR,10aS)-10a-Ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octa-hydro-phenanthrene-2,6-dicarbonitrile.

Project description:The anti-inflammatory and cytoprotective tricyclic title compound, C(21)H(18)N(2)O(2), also known as TBE-31, crystallizes with two nearly superimposable mol-ecules in the asymmetric unit. In both mol-ecules, the three ring systems conform to an envelope-chair-planar arrangement. The central ring, in a cyclohexane chair conformation, contains an axial ethynyl group that bends slightly off from a nearby axial methyl group because of the 1,3-diaxial repulsion between the two groups. In the crystal, weak C-H?N and C-H?O inter-actions form chains along [001].

| S-EPMC3515197 | biostudies-literature

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-2-yl acetate.

Project description:The hemisynthesis of the title compound, C22H32O2, was carried out through direct acetyl-ation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexa-hydro-phen-an-thren-2-ol]. The mol-ecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [-0.10 (6)] allowed this absolute configuration to be confirmed.

| S-EPMC3998421 | biostudies-literature

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-2-yl benzoate.

Project description:The title compound, C27H34O2, was hemisynthesized through direct benzoyl-ation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the mol-ecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.

| S-EPMC4158506 | biostudies-literature

7-(2-Chloro-phen-yl)-2,6,9-trimethyl-dibenzo[b,h][1,6]naphthyridine.

Project description:In the title compound, C(25)H(19)ClN(2), the dibenzo[b,h][1,6]naphthyridine system is planar to within 0.16 (2) Å, and the chloro-phenyl ring is inclined to it by 82.53 (7)°. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds, forming chains propagating in [100]. There are also a number of weak π-π stacking inter-actions present [centroid-centroid distances = 3.8531 (1) and 3.7631 (1) Å].

| S-EPMC3007939 | biostudies-literature

Crystal structure of (4b<i>S</i>,8a<i>R</i>)-1-isopropyl-4b,8,8-trimethyl-7-oxo-4b,7,8,8a,9,10-hexa-hydro-phenanthren-2-yl acetate.

Project description:The title compound, C22H28O3, was prepared by a direct acetyl-ation reaction of naturally occurring totarolenone. The mol-ecule contains three fused rings, which exhibit different conformations. The central ring has a half-chair conformation, while the non-aromatic oxo-substituted ring has a screw-boat conformation. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming sheets parallel to the bc plane. The carbonyl O atoms and the C atom at the 6-position of the cyclo-hexene ring are each disordered over two sets of sites with major occupancy components of 0.63 (7) and 0.793 (14), respectively.

| S-EPMC5947497 | biostudies-literature

5-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-Trimethyl-perhydro-3,12-ep-oxy-1,2-dioxepino[4,3-i]isochromen-10-yl]oxymeth-yl}benzene-1,3-diol.

Project description:The title compound, C(22)H(30)O(7), is a fused five-ring system that is of inter-est for its anti-cancer and anti-malarial activity. The six-membered C(6) and C(5)O rings display chair conformations. The six-membered C(3)O(3) ring containing the ether and per-oxy functionalities has a distorted boat conformation, with a C-O-O-C torsion angle of 42.6?(1)° for the per-oxy group. The seven-membered C(6)O ring has a distorted boat-type conformation, while the seven-membered C(5)O(2) ring has a very distorted chair-type conformation. The structure contains inter-molecular O-H?O and O-H?(O,O) bonds that link the mol-ecules into sheets parallel to the (100) planes.

| S-EPMC2968296 | biostudies-literature

Review of Oxepine-Pyrimidinone-Ketopiperazine Type Nonribosomal Peptides.

Project description:Recently, a rare class of nonribosomal peptides (NRPs) bearing a unique Oxepine-Pyrimidinone-Ketopiperazine (OPK) scaffold has been exclusively isolated from fungal sources. Based on the number of rings and conjugation systems on the backbone, it can be further categorized into three types A, B, and C. These compounds have been applied to various bioassays, and some have exhibited promising bioactivities like antifungal activity against phytopathogenic fungi and transcriptional activation on liver X receptor α. This review summarizes all the research related to natural OPK NRPs, including their biological sources, chemical structures, bioassays, as well as proposed biosynthetic mechanisms from 1988 to March 2020. The taxonomy of the fungal sources and chirality-related issues of these products are also discussed.

| S-EPMC7344746 | biostudies-literature