Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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.

SUBMITTER: Oubabi R

PROVIDER: S-EPMC4158506 | biostudies-other | 2014 Aug

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

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

Oubabi Radouane R Auhmani Aziz A Ait Itto My Youssef MY Auhmani Abdelwahed A Daran Jean-Claude JC

Acta crystallographica. Section E, Structure reports online 20140711 Pt 8

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. ...[more]

PMID: 25249914

Similar Datasets

(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

Crystal structure of (4bS,8aR)-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?? 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

2-[(8-Meth-oxy-carbonyl-4b,8-dimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-3-yl)amino]-3,5-dinitro-benzoic acid ethyl acetate monosolvate.

Project description:The title compound, C(25)H(27)N(3)O(8)·C(4)H(8)O(2), has a diterpene skeleton in which the fused cyclo-hexane rings exhibit chair and half-chair conformations. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds are observed.

| S-EPMC3435697 | biostudies-literature

Crystal structure of 7-isopropyl-1,4a,N-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodeca-hydro-phenanthrene-1-carb-ox-amide.

Project description:In the title compound, C26H37NO, a new derivative of di-hydro-abietic acid, the two cyclo-hexene rings adopt half chair conformations, whereas the cyclo-hexane ring has a chair conformation. Each of the methyl groups is in an axial position with respect to the tricyclic hydro-phenanthrene residue. In the crystal packing, methyl-ene-C-H⋯π(phen-yl) inter-actions lead to supra-molecular helical chains along [010]; the amide-H atom does not form a significant inter-molecular inter-action owing to steric pressure.

| S-EPMC4647402 | 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

(4aS,10aS)-7-Hydr-oxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene: a new diterpenoid compound.

Project description:The new title diterpenoid compound, C(20)H(30)O, is a natural product isolated from Tetra-clinis articulata wood via chloro-form extraction. The asymmetric unit contains four mol-ecules with the same S,S configuration, deduced from the chemical synthesis. Indeed, an overlay analysis, calculated using structure-matching software, shows that the four mol-ecules can be superimposed. The central ring has a half-chair conformation, whereas the saturated ring displays a chair conformation.

| S-EPMC2960765 | biostudies-literature

(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,-9,10,10a-octa-hydro-phenanthren-1-yl)-methanaminium 4-toluene-sulfonate.

Project description:In the title compound, C(20)H(32)N(+)·C(7)H(7)O(3)S(-), the configurations of the two chiral centers observed in the protonated cation are consistent with previous reports. In the crystal structure, weak inter-molecular N-H⋯O hydrogen bonds link ions into chains which develop along the a axis. The isopropyl group and four CH groups of the attached benzene ring are disordered approximately equally over two positions.

| S-EPMC2961293 | biostudies-literature

Methyl 4-(trimethyl-silylethyn-yl)benzoate.

Project description:The title compound, C(13)H(16)O(2)Si, was synthesized as a precursor for ethynylarene derivatives and crystallized from hexane. In the crystal structure, mol-ecules are linked by weak C-H?O hydrogen bonds to form chains that pack in layers in a herringbone fashion.

| S-EPMC2961551 | biostudies-literature

6,7,8,9-Tetra-hydro-4b,9b-dihy-droxy-indano[1,2-b]indoline-9,10-dione monohydrate.

Project description:In the title compound, C(15)H(13)NO(4)·H(2)O, the organic mol-ecule adopts a V-shaped conformation in which the dihedral angle between the five-membered rings is 68.33?(5)°. The cyclo-hexenone ring adopts an envelope conformation, with one of the methyl-ene C atoms displaced by 0.607?(4)?Å from the plane through the other atoms. In the crystal, inter-molecular N-H?(O,O) and O-H?O hydrogen bonds link the components into (001) sheeets and C-H?O inter-actions and aromatic ?-? stacking [centroid-centroid separation = 3.6176?(19)?Å] help to consolidate the packing.

| S-EPMC3007351 | biostudies-literature

1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodeca-hydro-phenanthrene-1-carboxylic acid.

Project description:The title compound, also known as isopimaric acid, C(20)H(30)O(2), was isolated from slash pine rosin. There are two unique mol-ecules in the unit cell. The two cyclo-hexane rings have classical chair conformations. The cyclo-hexene ring represents a semi-chair. The mol-ecular conformation is stabilized by weak intra-molecular C-H?O hydrogen-bonding inter-actions. The mol-ecules are dimerized through their carboxyl groups by O-H?O hydrogen bonds, forming R(2) (2)(8) rings.

| S-EPMC2969610 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data