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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 | 2008 Dec

REPOSITORIES: biostudies-literature

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

Badshah Amir A Hasan Aurangzeb A Barbarín Cecilia R CR Abbas Asghar A Ali Sajid S

Acta crystallographica. Section E, Structure reports online 20081210 Pt 1

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)°]. ...[more]

PMID: 21581709

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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⋯π interactions.

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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.

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

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(±)-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.

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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.

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(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⋯π inter-actions.

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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)°.

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