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Ethyl 6-(4-ethoxy-phen-yl)-4-(furan-2-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

ABSTRACT: The title compound, C(21)H(22)O(5), was prepared by NaOH-catalysed cyclo-condensation of 3-(4-ethoxy-phen-yl)-1-(furan-2-yl)prop-2-en-1-one with ethyl acetoacetate. In the crystal, C-H⋯O and C-H⋯π inter-actions link the mol-ecules. In the title mol-ecule, the furan and cyclo-hexene rings are almost parallel [6.77 (11)°] and the cyclo-hexene ring is approximately perpendicular to the benzene ring [84.79 (5)°].

SUBMITTER: Badshah A

PROVIDER: S-EPMC2967980 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Ethyl 6-(4-chloro-phen-yl)-4-(4-methoxy-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:In the title compound, C(22)H(21)ClO(4), the cyclo-hex-3-ene unit adopts an envelope conformation in both independent mol-ecules comprising the asymmetric unit. The two benzene rings are inclined to each other at a dihedral angle of 82.03?(5)° [86.37?(5)°]. In the crystal, the molecules interact via C-H?O, C-H?Cl and C-H?? interactions.

| S-EPMC2969664 | biostudies-literature

(1RS,6SR)-Ethyl 4,6-bis-(4-fluoro-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:In the crystal structure of the title compound, C(21)H(18)F(2)O(3), the cyclo-hexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 76.27?(8)° and their planes make dihedral angles of 16.65?(10) and 67.53?(7)° with the approximately planar part of the cyclo-hexenone ring [maximum deviation 0.044?(2)?Å, while the sixth atom is displaced by 0.648?(3)?Å from this plane]. In the crystal, weak inter-molecular C-H?O, C-H?F and C-H?? inter-actions join mol-ecules into a three-dimensional structure.

| S-EPMC3051537 | biostudies-literature

Ethyl 4-(4-bromo-phen-yl)-6-(4-ethoxy-phen-yl)-2-oxocyclo-hex-3-enecarboxyl-ate.

Project description:The title compound, C(23)H(23)BrO(4), is an inter-mediate in the synthesis of fused heterocycles. In the title mol-ecule, the cyclo-hexene ring has a distorted half-chair conformation. The bromo-phenyl ring and the mean plane of the cyclo-hexene ring form a dihedral angle of 13.8?(3)°, whereas the benzene and cyclo-hexene rings are approximately perpendicular [88.44?(17)°]. There are only weak C-H?O and C-H?? inter-molecular inter-actions.

| S-EPMC2968510 | biostudies-literature

(1RS,6SR)-Ethyl 4-(2,4-dichloro-phen-yl)-6-(4-fluoro-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(21)H(17)Cl(2)FO(3). Both these mol-ecules are very similar: the normal probability plots for bond lengths, angles and even for torsion angles show that the differences are of a statistical nature. A pseudocentre of symmetry is located between the symmetry-independent mol-ecules at [0.245?(1), 0.535?(19), 0.909?(1)]. The cyclo-hexene rings have slightly distorted sofa conformations in both mol-ecules and the two benzene rings are inclined by dihedral angles of 61.33?(14) and 62.85?(14)°. In the crystal, relatively short inter-molecular C-H?O inter-actions join mol-ecules into homomolecular (i.e. ?AAA? and ?BBB?) chains along the b axis. These chains are inter-connected by further heteromolecular C-H?O inter-actions.

| S-EPMC3051448 | biostudies-literature

Ethyl 4-(4-bromo-phen-yl)-6-r-phenyl-2-oxocyclo-hex-3-ene-1-t-carboxyl-ate.

Project description:In the title compound, C(21)H(19)BrO(3), the cyclo-hexene ring adopts an envelope conformation, with all substituents equatorial. The plane through its five coplanar atoms makes dihedral angles of 28.88?(10) and 71.94?(10)° with the bromo-benzene and phenyl rings, respectively. The dihedral angle between the latter two rings is 51.49?(15)°. Inter-molecular C-H?O hydrogen bonds are found in the crystal structure; a C-H?? inter-action is also present.

| S-EPMC3007547 | biostudies-literature

Ethyl 4-(2,4-dichloro-phen-yl)-6-(6-meth-oxy-2-naphth-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:In the title compound, C(26)H(22)Cl(2)O(4), the cyclo-hexenone ring adopts an approximate half-chair conformation, with two C atoms displaced by -0.485?(6) and 0.218?(6)?Å from the plane of the other four ring atoms. The dihedral angles between its four almost coplanar [maximum deviation = 0.006?(2)?Å] atoms and the benzene and naphthalene ring systems are 59.26?(13) and 79.94?(9)°, respectively. The dihedral angle between the aromatic rings systems is 77.14?(7)°. A short intra-molecular C-H?Cl contact generates an S(6) ring. In the crystal, mol-ecules are linked by C-H?O and C-H?Cl inter-actions to generate a three-dimensional network.

| S-EPMC2983411 | biostudies-literature

(1RS,6SR)-Ethyl 4-(4-chloro-phen-yl)-6-(4-fluoro-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate toluene hemisolvate.

Project description:In the crystal structure of the title compound, C(21)H(18)ClFO(3)·0.5C(7)H(8), the toluene solvent mol-ecules occupy special positions on centres of symmetry, and consequently are disordered across this site. The cyclo-hexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 72.90?(7)° and their planes make dihedral angles of 30.09?(10) (chloro-phen-yl) and 88.13?(6)° (fluoro-phen-yl) with the approximately planar part of the cyclo-hexenone ring [maximum deviation from plane through five atoms is 0.030?(2)?Å, the sixth atom is 0.672?(3)Å out of this plane]. Weak inter-molecular C-H?O and C-H?X (X = F, Cl) inter-actions join mol-ecules into a three-dimensional structure. Also, a relatively short and directional C-Cl?F-C contact is observed [Cl?F = 3.119?(2)?Å, C-Cl?F = 157.5?(2)° and C-F?Cl 108.3?(2)°]. The solvent mol-ecules fill the voids in the crystal structure and are kept there by relatively short and directional C-H?? inter-actions.

| S-EPMC3051615 | biostudies-literature

Ethyl 6-(4-bromo-phen-yl)-4-(4-fluoro-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(21)H(18)BrFO(3), in which the dihedral angles between the fluoro-phenyl and bromo-phenyl groups are 77.0?(1) and 85.8?(1)°. In one of the mol-ecules, two methine C-H groups of the cyclo-hexene ring are disordered over two sets of sites in a 0.53?(2):0.47?(2) ratio. In both mol-ecules, the atoms of the ethyl group were refined as disordered over two sets of sites with occupancies of 0.67?(2):0.33?(2) and 0.63?(4):0.37?(4). The cyclo-hexene rings have slightly distorted sofa conformations in both mol-ecules. In the crystal, C-H?O inter-actions link mol-ecules into chains along the b axis.

| S-EPMC3470264 | biostudies-other

Ethyl 6-(6-meth-oxy-naphthalen-2-yl)-4-(naphthalen-2-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:The title compound, C30H26O4, contains an oxo-cyclo-hexane ring in a distorted half-chair configuration, with disorder of two C atoms in a 0.859?(4):0.141?(4) ratio. The dihedral angle between the mean planes of the two napthalene ring systems is 58.6?(8)°.

| S-EPMC3588453 | biostudies-literature

(±)-Ethyl 6-(6-meth-oxy-2-naphth-yl)-4-(4-methyl-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

Project description:In the title compound, C(27)H(26)O(4), the dihedral angle between the naphthalene ring system and the benzene ring is 73.10?(5)°. In the crystal, a weak C-H?O inter-action occurs. Two C-H groups of the cyclo-hexene ring are disordered over two sets of sites in a 0.796?(5):0.204?(5) ratio, which corresponds to partial overlap of the two enanti-omeric mol-ecules.

| S-EPMC2969816 | biostudies-other

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