Browse
Submit Data
Databases
API
Help

Dataset Information

27 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thien-yl)perhydro-pyrrolo[3,4-d][1,2]oxazole-4,6-dione.

ABSTRACT: The crystal structure of the title compound, C(17)H(16)N(2)O(3)S, exhibits intra-molecular C-H?S and inter-molecular C-H?S and C-H?O hydrogen bonds, C-S?N [S?N = 3.033?(2)?Å and C-S?N = 142.76?(9)°] inter-actions, and C-H?? inter-actions; these inter-actions generate S(4), S(6) and R(2) (2)(14) ring motifs. The isoxazole ring adopts an envelope conformation, with the N atom displaced by 0.672?(2)?Å from the plane of the other ring atoms. The thio-phene ring is oriented with respect to the succinimide and phenyl rings at dihedral angles of 40.03?(12) and 5.21?(13)°, respectively. The dihedral angle between the succinimide and phenyl rings is 39.38?(12)°.

SUBMITTER: Odabasoglu M

PROVIDER: S-EPMC2962057 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thien-yl)perhydro-pyrrolo[3,4-d][1,2]oxazole-4,6-dione.

Odabaşoğlu Mustafa M Ozkan Hamdi H Yıldırır Yılmaz Y Büyükgüngör Orhan O

Acta crystallographica. Section E, Structure reports online 20080705 Pt 8

The crystal structure of the title compound, C(17)H(16)N(2)O(3)S, exhibits intra-molecular C-H⋯S and inter-molecular C-H⋯S and C-H⋯O hydrogen bonds, C-S⋯N [S⋯N = 3.033 (2) Å and C-S⋯N = 142.76 (9)°] inter-actions, and C-H⋯π inter-actions; these inter-actions generate S(4), S(6) and R(2) (2)(14) ring motifs. The isoxazole ring adopts an envelope conformation, with the N atom displaced by 0.672 (2) Å from the plane of the other ring atoms. The thio-phene ring is oriented with respect to the succin ...[more]

PMID: 21203142

Similar Datasets

2-Methyl-3-(5-methyl-2-thien-yl)-5-phenyl-perhydro-pyrrolo[3,4-d]isoxazole-4,6-dione.

Project description:In the mol-ecule of the title compound, C(17)H(16)N(2)O(3)S, the phenyl ring is oriented with respect to the thio-phene and succinimide rings at dihedral angles of 88.08?(3) and 57.81?(3)°, respectively; the dihedral angle between the thio-phene and succinimide rings is 35.69?(3)°. The isoxazole ring adopts an envelope conformation with the N atom at the flap position. In the crystal structure, inter-molecular C-H?O hydrogen bonds link the mol-ecules into infinite chains along the b axis. Weak C-H?? inter-actions may further stabilize the structure.

| S-EPMC2968779 | biostudies-literature

2,5-Dimethyl-3-(3-methyl-thio-phen-2-yl)perhydro-pyrrolo[3,4-d]isoxazole-4,6-dione.

Project description:The crystal structure of the title compound, C(12)H(14)N(2)O(3)S, exhibits intra-molecular C-H?S and inter-molecular C-H?S, C-H?O hydrogen bonds, C-S?N [S?N = 2.980?(2)?Å, C-S?N = 145.78?(17)°] and C-H?? inter-actions; these inter-actions generate two C(5) chains and S(4), S(6) and R(4) (4)(28) ring motifs. The isoxazole ring has an envelope conformation; the N atom, which is the flap atom, is displaced by 0.261?(2)?Å from the plane defined by the remaining four atoms. The dihedral angle between the succinimide and thio-phene rings is 46.8?(2)°.

| S-EPMC2961365 | biostudies-literature

(3R,3aS,6R,6aR)-3-(1-Nitro-eth-yl)perhydro-furo[3,2-b]furan-3,6-diol.

Project description:The mol-ecule of the title compound, C(8)H(13)NO(6), a sucrose derivative, consists of two fused tetra-hydro-furan rings having the cis arrangement at the ring junctions, giving a V-shaped mol-ecule. An intra-molecular O-H?O inter-action occurs. Inter-molecular O-H?O hydrogen bonds help to stabilize the crystal structure.

| S-EPMC3007024 | biostudies-literature

(3R,8aS)-3-Ethyl-perhydro-pyrrolo[1,2-a]pyrazine-1,4-dione.

Project description:In the title compound, C(9)H(14)N(2)O(2), the pyrrolidine and piperazine rings adopt envelope and boat conformations, respectively. The chiral centers were assigned on the basis of the known stereogenic center of an enanti-omerically pure starting material and the trans relationship between the H atoms attached to these centers. The crystal packing is stabilized by an inter-molecular hydrogen bond between the N-H group and a carbonyl O atom of the diketopiperazine group, forming zigzag C(5) chains along [010].

| S-EPMC2979809 | biostudies-other

Practical Synthesis of the Bicyclic Darunavir Side Chain: (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol from Monopotassium Isocitrate.

Project description:A practical synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol-a key intermediate in the synthesis of darunavir-from monopotassium isocitrate is described. The isocitric acid salt, obtained from a high-yielding fermentation fed by sunflower oil, was converted in several steps to a tertiary amide. This amide, along with the compound's ester functionalities, was reduced with lithium aluminum hydride to give, on acidic workup, a transient aminal-triol. This was converted in situ to the title compound, the bicyclic acetal furofuranol side chain of darunavir, a protease inhibitor used in treatment of HIV/AIDS. Key to the success of this process was identifying an optimal amide that allowed for complete reaction and successful product isolation. N-Methyl aniline amide was identified as the most suitable substrate for the reduction and the subsequent cyclization to the desired product. Thus, the side chain is produced in 55% overall yield from monopotassium isocitrate.

| S-EPMC5437813 | biostudies-literature

(3aR,6aR)-1-Phenyl-5-[(R)-1-phenyl-ethyl]-3-[4-(trifluoro-meth-yl)phen-yl]-1,6a-dihydro-pyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione.

Project description:In the title mol-ecule, C(26)H(20)F(3)N(3)O(2), the two central five-membered rings form a dihedral angle of 62.94?(8)°. The absolute configuration was determined by analysis of Bijvoet pairs based on resonant scattering of light atoms, yielding a Hooft parameter y = -0.05?(11). Notable intra- and inter-molecular contacts include C-H?O and C-H??(arene) hydrogen bonds.

| S-EPMC2971765 | biostudies-literature

(3R,6S,7aS)-3-Phenyl-6-(phenyl-sulfan-yl)perhydro-pyrrolo[1,2-c]oxazol-5-one.

Project description:Mol-ecules of the title compound [systematic name: (2R,5S,7S)-2-phenyl-7-phenyl-sulfanyl-1-aza-3-oxa-bicyclo-[3.3.0]octan-8-one], C(18)H(17)NO(2)S, form high quality crystals even though they are only packed using C-H?O(carbon-yl) and weak C-H?S inter-actions. The dihedral angle between the aromatic rings is 85.53?(5)°. The fused rings adopt envelope and twist conformations.

| S-EPMC2977644 | biostudies-literature

3-(6-Benz-yloxy-2,2-dimethyl-perhydro-furo[2,3-d][1,3]dioxol-5-yl)-5-(4-bromo-phen-yl)-2-phenyl-perhydro-pyrrolo[3,4-d]isoxazole-4,6-dione.

Project description:In the title compound, C(31)H(29)BrN(2)O(7), the isoxazolidine ring adopts a twist conformation, while the tetrahydrofuran, dioxolone and pyrrole rings adopt envelope conformations. The structure is stabilized by inter-molecular C-H?O hydrogen bonds and C-H?? inter-actions.

| S-EPMC2977822 | biostudies-other

2,5-Dihexyl-3,6-diphenyl-pyrrolo-[3,4-c]pyrrole-1,4(2H,5H)-dione.

Project description:The asymmetric unit of the title compound, C(30)H(36)N(2)O(2), contains one half-mol-ecule, the other half being generated by a crystallographic inversion centre. The crystal structure is devoid of any classical hydrogen bonds however, non-classical C-H?O inter-actions link the mol-ecules into chains propagating in [001] and a C-H?? inter-action leads to the formation of a two-dimensional network in (011).

| S-EPMC3006905 | biostudies-other

(3S,3aS,6R,6aR)-2-Oxohexa-hydro-furo[3,2-b]furan-3,6-diyl dibenzoate.

Project description:The title compound, C20H16O7, contains a cis-fused ?-lactone tetra-hydro-furan ring system functionalized with two benzo-yloxy groups. Both rings adopt an envelope conformation. The mol-ecule assumes an elongated shape and exibits non-crystallographic C 2 symmetry. The benzo-yloxy groups are almost planar [maximum deviations of 0.0491?(15) and 0.0336?(17)?Å for the O atoms] and their mean planes are inclined to one another by 16.51?(4)°. The crystal packing features weak C-H?O inter-actions. The aryl groups of adjacent mol-ecules are parallel shifted with face-to-face contacts and a shortest inter-molecular C?C distance of 3.482?(4)?Å.

| S-EPMC3790370 | 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