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Rac-(2R,3S)-2-Phenyl-3-(3-phenyl-1,2,3,4-tetra-hydro-quinoxalin-2-yl)quinoxaline.

ABSTRACT: The title compound, C(28)H(22)N(4), is the unexpected by-product of the reaction of 2-hydroxy-acetophenone and 1,2-diamino-benzene under iodine catalysis, during which a carbon-carbon ?-bond between two quinoxaline units was formed. Although a fully oxidized title compound should sterically be possible, only one quinoxaline ring is fully oxidized while the second ring remains in the reduced form. As expected, the tetra-hydro-quinoxaline unit is not planar; it adopts a sofa conformation, whereby the atom joining the two heterocyclic systems lies out of the plane of the other atoms. The quinoxaline ring system makes a dihedral angle of 53.61?(4)° with its phenyl ring substituent. The crystal packing is determined by pairs of N-H?N, N-H?? and weak C-H?N hydrogen bonds, forming a chain parallel to the a axis.

SUBMITTER: Ammermann S

PROVIDER: S-EPMC2961777 | biostudies-literature |

REPOSITORIES: biostudies-literature

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[(2R,3S,5R)-3-Acet-oxy-5-(5-formyl-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-1-yl)-2,3,4,5-tetra-hydro-furan-2-yl]methyl acetate.

Project description:In the two independent but very similar mol-ecules (A and B) of the title compound, C(14)H(16)N(2)O(8), both six-membered pyrimidine rings are nearly planar [maximum deviations = 0.010?(3)?Å in A and 0.028?(3)?Å in B]. The five-membered furan-ose ring in mol-ecule A adopts an envelope conformation, while the same ring in mol-ecule B has a twisted conformation. In the crystal, the A mol-ecules are linked via a pair of inter-molecular N-H?O hydrogen bonds, forming dimers. Each A mol-ecule is further linked to a B mol-ecule via a second N-H?O hydrogen bond. There are also a number of C-H?·O inter-actions present, leading to the formation of a three-dimensional network.

| S-EPMC3247360 | biostudies-literature

[(1R,3S)-6,7-Dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinolin-3-yl]methanol 2.33-hydrate.

Project description:The title compound, C(18)H(21)NO(3)·2.33H(2)O, is the fourth reported member in a series of (1R,3S)-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinoline derivatives used in catalysis as ligands (or their precursors). The N-heterocycle in the structure adopts a half-chair conformation. The dihedral angle between the benzene rings is 77.29?(13)°. There are three ill-resolved water molecules of crystallization in the structure (one of them rotationally disordered about a threefold axis) involved in short contacts probably due to hydrogen bonding.

| S-EPMC3052049 | biostudies-literature

2-[(1R,3S)-6,7-Dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinolin-3-yl]-4-phenyl-1,3-thia-zole.

Project description:In the title compound, C(26)H(24)N(2)O(2)S, the dihedral angle between the thia-zole ring and the adjacent phenyl ring is 3.02?(15)°. The N-containing six-membered ring of the tetra-hydro-isoquinoline unit adopts a half-chair conformation. The dihedral angle between the least-squares plane of the tetra-hydro-isoquinoline ring system and its nearest phenyl ring is 76.90?(13)°. No classical hydrogen bonds nor ?-? inter-actions were found in the crystal structure.

| S-EPMC3201443 | biostudies-literature

{(1R,3S)-2-Benzyl-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinolin-3-yl}diphenyl-methanol.

Project description:In the title compound, C(37)H(35)NO(3), a precursor to novel chiral catalysts, the N-containing six-membered ring assumes a half-chair conformation. Inter-molecular C-H?O hydrogen bonds link the mol-ecules in the crystal structure.

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Crystal structure of (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetra-hydro-isoquinolin-2-yl]-1,2-di-phenyl-ethanol.

Project description:The synthesis and crystal structure of the title compound, C30H29NO, are described. This compound is a member of the chiral di-hydro-iso-quinoline-derived family, used as building blocks for functional materials and as source of chirality in asymmetric synthesis, and was isolated as one of two diastereomeric β-amino alcohols, the title mol-ecule being found to be the (S,R) diastereoisomer. In the crystal, mol-ecules are packed in a herringbone manner parallel to (103) and (10) via weak C-H⋯O and C-H⋯π(ring) inter-actions. Hirshfeld surface analysis showed that the surface contacts are predominantly H⋯H inter-actions (ca 75%). The crystal studied was refined as a two-component inversion twin.

| S-EPMC6775741 | biostudies-literature

(1S,3S)-Methyl 6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxyl-ate.

Project description:In the title compound, C(19)H(21)NO(4), an organocatalyst with a tetra-hydro-isoquinoline backbone, the heterocyclic ring assumes a half-boat conformation. The dihedral angle between the aromatic rings is 82.93?(8)°. In the crystal, mol-ecules are linked via N-H?O and C-H?O hydrogen bonds, forming a layer parallel to (10[Formula: see text]).

| S-EPMC3120575 | biostudies-literature

2-Methyl-1,2,3,4-tetra-hydro-isoquinolin-6-yl N-phenyl-carbamate.

Project description:In the mol-ecule of the title compound, C(17)H(18)N(2)O(2), the piperidine ring adopts a half-chair form. The two benzene rings are individually planar and make a dihedral angle of 53.90°. The crystal structure is stabilized by inter-molecular N-H?N hydrogen bonds and ?-? stacking inter-actions (centroid-centroid distance = 3.962?Å).

| S-EPMC2977739 | biostudies-literature

rac-1,2,3,4-Tetra-hydro-1,4-methano-anthracene-6,7-dicarbonitrile.

Project description:The title compound, C(17)H(12)N(2), comprises a norbornane unit having a dicyanona-phthalene ring fused on one side. Both cyano groups are twisted slightly out of the plane of the naphthalene ring system [C-C-C-C torsion angle = 1.9 (2)°]. In the crystal, inversion-related mol-ecules are linked by pairs of weak C-H⋯N hydrogen bonds, forming dimers.

| S-EPMC3238964 | biostudies-literature

(1R,3S)-Methyl 2-benzyl-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxyl-ate.

Project description:In the title compound, C(26)H(27)NO(4), a precursor to novel chiral catalysts, the N-containing six-membered ring assumes a half-boat conformation. Various C-H?? interactions and intermolecular short contacts (C?H = 2.81-2.90?Å) link the mol-ecules together in the crystal structure.

| S-EPMC2972025 | biostudies-literature

(1S,3S)-Methyl 2-benzyl-6,7-dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxyl-ate.

Project description:In the title compound, C(26)H(27)NO(4), the heterocyclic ring assumes a half-chair conformation and inter-molecular C-H?O inter-actions help to construct the three-dimensional network within the crystal packing.

| S-EPMC3120496 | biostudies-literature

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