Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing.

ABSTRACT: We report a new synthetic route to 5,11-disubstituted indeno[1,2-b]fluorene-6,12-diones that is amenable to larger scale reactions, allowing for the preparation of gram amounts of material. With this new methodology, we explored the effects on crystal packing morphology for the indeno[1,2-b]fluorene-6,12-diones by varying the substituents on the silylethynyl groups.

SUBMITTER: Rose BD

PROVIDER: S-EPMC4168888 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing.

Rose Bradley D BD Santa Maria Peter J PJ Fix Aaron G AG Vonnegut Chris L CL Zakharov Lev N LN Parkin Sean R SR Haley Michael M MM

Beilstein journal of organic chemistry 20140905

We report a new synthetic route to 5,11-disubstituted indeno[1,2-b]fluorene-6,12-diones that is amenable to larger scale reactions, allowing for the preparation of gram amounts of material. With this new methodology, we explored the effects on crystal packing morphology for the indeno[1,2-b]fluorene-6,12-diones by varying the substituents on the silylethynyl groups. ...[more]

PMID: 25246970

Similar Datasets

6,12-Bis[(tri-cyclo-hexyl-sil-yl)ethyn-yl]indeno-[1,2-b]fluorene.

Project description:The title compound, C60H76Si2, a formally anti-aromatic system containing 20-π electrons, contains a rare p-xylylene motif. This is displayed by the alternating short and long bonds. The outer rings possess nearly homogenous bond lengths. In the crystal, the molecules forms layers perpendicular to the c axis and within these layers there are two one-dimensional stacks with one stack that has a sp (2) carbon contact of 3.283 (6) Å, less than the sum of the van der Waals radii. The center of the mol-ecule sits on an inversion center.

| S-EPMC3685047 | biostudies-literature

6-Ferrocenoyl-7-phenyl-spiro-[hexa-hydro-pyrrolo-[1,2-c][1,3]thia-zole-5,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, [Fe(C5H5)(C32H24N3OS)], both the thia-zolidine ring and the pyrrolidine ring adopt an envelope conformation, with the S atom and the phenyl-bearing C atom, respectively, as the flaps. The thia-zolidine ring mean plane makes a dihedral angle of 59.08?(11)° with the pyrrolidine ring mean plane, which in turn makes a dihedral angle of 83.40?(10)° with the cyclo-pentane ring, indicating that the latter two rings are almost orthogonal to one another. In the crystal, a pair of C-H?O hydrogen bonds link the mol-ecules forming inversion dimers. The dimers are linked via ?-? inter-actions [centroid-centroid distance = 3.7764?(10)?Å] involving the quinoxaline moieties forming chains propagating along [1-10].

| S-EPMC3884422 | biostudies-literature

5,11-Dimethyl-6,12-dimeth-oxy-indolo[3,2-b]carbazole.

Project description:The title compound, C(22)H(20)N(2)O(2), was prepared in a twofold Cadogan cyclization followed by double N-methyl-ation. The crystal structure is characterized by a zigzag arrangement of centrosymmetric mol-ecules. The indolocarbazole framework is essentially planar [maximum deviation = 0.028 (2) Å] and the meth-oxy groups are orthogonal to this plane [C-C-O-C torsion angle = -88.2 (2)°]. The lengths of the C-N bonds are nearly identical and all C-C bonds of the pyrrole subunit are significantly longer than the C-C bonds in the benzene rings.

| S-EPMC3569787 | biostudies-literature

6-Ferrocenoyl-7-(4-fluoro-phen-yl)spiro-[hexa-hydro-pyrrolo-[1,2-c][1,3]thia-zole-5,11'-indeno-[1,2-b]quinoxaline].

Project description:In the title compound, [Fe(C5H5)(C32H23FN3OS)], both the thia-zolidine ring and the pyrrolidine ring adopt a twist conformation on the N-C(H) bridging bond. Their mean planes are inclined to one another by 10.05?(10)°, and they make dihedral angles of 82.09?(10) and 89.67?(11)°, respectively, with the cyclo-pentane ring. The F atom deviates by -0.0238?(2)?Å from the benzene ring to which it is attached. In the crystal, mol-ecules are linked by a pair of C-H?O hydrogen bonds, forming inversion dimers.

| S-EPMC3884446 | biostudies-literature

5,11-Dimethyl-dibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dione.

Project description:In the mol-ecule of the title compound, C(16)H(14)N(2)O(2), an N,N'-dimethyl-dianthranilide, the two methyl groups are disordered over two positions; site occupation factors were kept fixed as 0.75:0.25 and 0.65:0.35. The dihedral angle between the two benzene rings is 75.57 (3)°.

| S-EPMC2960302 | biostudies-literature

5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazo-cine-6,12-dione acetic acid hemisolvate.

Project description:The mol-ecular structure of the title compound, C28H22N2O6S2·0.5CH3COOH, is built up from three fused rings, two six and one eight membered. The eight-membered ring shows a boat conformation and the dihedral angle between the two benzene groups attached thereto is 66.43 (11)°, resulting in a V-shaped geometry. Two tosyl substituents are bound to the N atoms. The planes through the tolyl rings are roughly perpendicular, as indicated by the dihedral angle of 82.44 (12)°. In the crystal, the mol-ecule and its inversion-related symmetry-equivalent are linked to the acetic acid solvent mol-ecule by non-classical O-H⋯O and C-H⋯O hydrogen bonds. Two half-occupied acetic acid solvent mol-ecules are disordered at the same site and linked by a center of symmetry.

| S-EPMC3629651 | biostudies-literature

11H-Indeno-[1,2-b]quinoxalin-11-one.

Project description:In the title compound, C(15)H(8)N(2)O, the fused ring system is approximately planar, with a maximum deviation of 0.039?(1)?Å. In the crystal, weak inter-molecular C-H?O inter-actions help to establish the packing.

| S-EPMC2979415 | biostudies-literature

6,12-Dihydro-dipyrido[1,2-a:1',2'-d]pyrazinium bis-(perchlorate).

Project description:In the title compound, C(12)H(12)N(2) (2+)·2ClO(4) (-), the dihedral angle between the two outer pyridine rings of the dication is 44.8 (1)°. In the crystal, weak intermolecular C-H⋯O hydrogen bonds occur.

| S-EPMC2969923 | biostudies-literature

Molecular Modeling of Indeno [1, 2-b] Quinoline-9, 11-Diones as Cytotoxic Agents.

Project description:Deoxyribonucleic acid (DNA) is an important molecular target for anti-cancer agents due to its involvement in gene expression and protein synthesis which are fundamental steps in cell division and growth. A number of antineoplastic agents interfere with DNA and hence disturb the cell cycle. Compounds including planar aromatic rings are privileged scaffolds in binding to DNA. This characteristic is mainly arisen from the fact that such structural feature may be appropriate to insert between the base pairs of the DNA double helix and produce relatively stable non-covalent complexes. Besides π-π stacking interactions, binding to the DNA molecule might be intensified through H-bond interactions of heterocyclic rings. In the present contribution, a series of experimentally validated cytotoxic indeno[1,2-b]quinoline-9,11-diones (1-12) and their aromatized analogues (13-21) developed in our group were subjected to docking and molecular dynamics simulations to elucidate their most probable binding modes with DNA.

| S-EPMC6269552 | biostudies-literature

A computational study of base-catalyzed reactions of cyclic 1,2-diones: cyclobutane-1,2-dione.

Project description:The reaction of cyclobutane-1,2-dione with hydroxide was studied by a variety of ab initio (MP2, SCS-MP2, CCSD(T), CEPA/1) and density functional (M06-2X) methods. Three possible reaction paths of the initially formed tetrahedral adduct leading to either 1-hydroxycyclopropane-1-carboxylate (benzilic acid type rearrangement, path A), α-oxobutanoate (path B) or γ-oxobutanoate (path C) were considered. Although the latter two products show similar or even more negative Gibbs free energies of reaction than calculated for the benzilic acid type rearrangement, the Gibbs free energies of activation are substantially higher. According to the calculations, the only feasible reaction appears to be the formation of 1-hydroxycyclopropane-1-carboxylate, which is corroborated by previous experimental observations.

| S-EPMC3628910 | 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