Browse
Submit Data
Databases
API
Help

Dataset Information

23 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Ethyl 6-methyl-4-[2-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)thio-phen-3-yl]-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

ABSTRACT: A new Biginelli compound, C(18)H(25)BN(2)O(4)S(2), containing a boronate ester group was synthesized from a lithium bromide-catalysed reaction. The compound crystallizes with two independent mol-ecules in the asymmetric unit that differ mainly in the conformation of the ester functionality. The crystal structure is stabilized by inter-molecular N-H?O and N-H?S hydrogen bonds involving the 3,4-dihydro-pyrimidine-2(1H)-thione NH groups as donors and the carbonyl O and thio-phene S atoms as acceptors.

SUBMITTER: Decken A

PROVIDER: S-EPMC2961284 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Ethyl 6-methyl-4-[2-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)thio-phen-3-yl]-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Decken Andreas A Zamora Matthew T MT Duguay Dominique R DR Vogels Christopher M CM Westcott Stephen A SA

Acta crystallographica. Section E, Structure reports online 20080426 Pt 5

A new Biginelli compound, C(18)H(25)BN(2)O(4)S(2), containing a boronate ester group was synthesized from a lithium bromide-catalysed reaction. The compound crystallizes with two independent mol-ecules in the asymmetric unit that differ mainly in the conformation of the ester functionality. The crystal structure is stabilized by inter-molecular N-H⋯O and N-H⋯S hydrogen bonds involving the 3,4-dihydro-pyrimidine-2(1H)-thione NH groups as donors and the carbonyl O and thio-phene S atoms as accepto ...[more]

PMID: 21202410

Similar Datasets

Ethyl 4-(4-chloro-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:In the title compound, C(14)H(15)ClN(2)O(2)S, the tetra-hydro-pyrimidine ring adopts a twisted boat conformation with the carbonyl group in an s-trans conformation with respect to the C=C double bond of the six-membered tetra-hydro-pyrimidine ring. The mol-ecular conformation is determined by an intra-molecular C-H?? inter-action. The crystal structure is further stabilized by inter-molecular N-H?O mol-ecular chains and centrosymmetric N-H?S dimers.

| S-EPMC2970428 | biostudies-literature

Ethyl 4-(4-cyano-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(15)H(15)N(3)O(2)S, contains two independent mol-ecules corresponding to the R and S enanti-omers. The dihydro-pyrimidinone rings adopt a flattened boat conformation. One of the ethyl groups is disordered over two orientations with occupancy factors of 0.700?(7) and 0.300?(7). In the crystal structure, mol-ecules are linked by inter-molecular N-H?O hydrogen-bonding inter-actions into one-dimensional chains along the c-axis direction. The chains are further connected by N-H?S hydrogen bonds, forming a three-dimensional network.

| S-EPMC2977496 | biostudies-literature

Ethyl 4-(4-hydroxy-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate monohydrate.

Project description:In the organic mol-ecule of the title compound, C(14)H(16)N(2)O(3)S·H(2)O, the two rings are oriented at a dihedral angle of 84.31?(2)°. In the crystal structure, intra-molecular O-H?O and inter-molecular O-H?O, N-H?O, O-H?S and N-H?S hydrogen bonds are found.

| S-EPMC2915317 | biostudies-literature

1,3-Dimethyl 5-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxyl-ate.

Project description:The title compound, C(16)H(21)BO(6), has has approximate C(2) symmetry, but no crystallographically imposed mol-ecular symmetry. In the crystal, mol-ecules are packed into parallel columns along the a axis. Short inter-molecular C-H⋯O contacts stabilize the crystal packing.

| S-EPMC3274972 | biostudies-literature

Ethyl 4-(2,4-difluoro-phen-yl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(20)H(18)F(2)N(2)O(2)S, contains four independent mol-ecules, two of which are paired into a dimer by way of two N-H?S hydrogen bonds. The other two independent mol-ecules are paired into two centrosymmetric dimers via pairs of inter-molecular N-H?S hydrogen bonds. In one mol-ecule, the carboxyl-ate O atoms, methyl-ene and methyl groups attached to the benzene ring are disordered between two positions in a 0.908?(3):0.092?(3) ratio. In two of the independent mol-ecules, the F and H atoms of the diflourophenyl ring are flip-flop disordered (i.e. by 180° about the C-C bond axis linking the ring to the rest of the molecule) in a 3:2 ratio. The crystal packing is stabilized by weak inter-molecular C-H?O hydrogen bonds.

| S-EPMC2977677 | biostudies-literature

2-(4-Ferrocenylphen-yl)-4,4,5,5-tetra-methyl-1,3,2-dioxaborolane.

Project description:In the title compound,, [Fe(C(5)H(5))(C(17)H(20)BO(2))], the two near parallel cyclo-penta-dienyl rings of the ferrocene group are eclipsed. The benzene ring is tilted with respect to the attached cyclo-penta-diene ring by 17.0 (1)° and by 24.2 (1)° with respect to the dioxaborolane ring. The mol-ecules assemble in the crystal via C-H⋯π inter-actions between the cyclo-penta-dienyl H atoms and the benzene and cyclo-penta-dienyl rings of neighbouring mol-ecules.

| S-EPMC2959994 | biostudies-literature

Ethyl 4-(2-bromo-5-fluoro-phen-yl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:In the title mol-ecule, C(20)H(18)BrFN(2)O(2)S, the pyrimidine ring adopts a flattened envelope conformation. The halogenated benzene ring is orthogonal to the planar part of the pyrimidine ring [dihedral angle = 89.05?(4)°], while the other phenyl ring is oriented at an angle of 85.14?(5)°. The ethoxy group is disordered over two orientations with site occpancies of ca 0.869?(4) and 0.131?(4). Intra-molecular C-H?Br and C-H?O hydrogen bonds generate S(5) and S(6) ring motifs. The crystal structure is stabilized by inter-molecular N-H?S, C-H?F, C-H?O and C-H?Br hydrogen bonds.

| S-EPMC2962151 | biostudies-literature

4,4,5,5-Tetra-methyl-2-[1,3,6,8-tetra-bromo-7-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane.

Project description:The complete mol-ecule of the title compound, C(28)H(28)B(2)Br(4)O(4), is generated by the application of a centre of inversion. In the mol-ecule, the BO(2) plane is perpendicular to that through the pyrene ring [dihedral angle = 86.27?(13)°]. In the crystal, mol-ecules stack into columns along the b axis, the closest contact between these being of the type C-Br??.

| S-EPMC3297842 | biostudies-other

Crystal structure of ethyl 6-methyl-2-sulfanyl-idene-4-(thio-phen-2-yl)-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:In the title compound, C12H14N2O2S2, the di-hydro-pyrimidine ring adopts a sofa conformation, with the C atom bearing the thienyl ring lying above the plane of the five remaining approximately coplanar (r.m.s. deviation = 0.0405?Å) atoms of the ring. The dihedral angle between the five near coplanar atoms of the ring and the thienyl ring is 89.78?(11)°. In the crystal, mol-ecules are linked into a supra-molecular chain along [100] via N-H?O(carbon-yl) hydrogen bonds. Inversion-related chains are linked into double chains via N-H?S(thione) hydrogen bonds. The three-dimensional architecture also features meth-yl-thienyl C-H?? inter-actions.

| S-EPMC4384618 | biostudies-literature

9-Phenyl-3,6-bis-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole.

Project description:In the title compound, C(30)H(35)B(2)NO(4), the carbazole skeleton is essentially planar (r.m.s. deviation for all non-H atoms = 0.035?Å), and is oriented at a dihedral angle of 65.0?(3)° with respect to the adjacent phenyl ring.

| S-EPMC3212309 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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