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(E)-3-[3,4-Bis(meth-oxy-methoxy)phen-yl]-1-(7-hy-droxy-5-meth-oxy-2,2-dimethyl-chroman-8-yl)prop-2-en-1-one.

ABSTRACT: The reaction of 5,6-(2,2-dimethyl-chroman-yl)-2-hy-droxy-4-meth-oxy-acetophenone and 3,4-bis-(meth-oxy-meth-yloxy)benzaldehyde affords the intense orange title chalcone derivative, C(25)H(30)O(8). The two benzene rings are connected through a -C(=O)-CH=CH- (propenone) unit, which is in an E conformation; the ring with the hy-droxy substitutent is aligned at 19.5?(2)° with respect to this unit, whereas the ring with the meth-oxy-meth-yloxy substituent is aligned at 9.3?(3)°. The dihedral angle between the rings is 19.38?(10)°. The hy-droxy group engages in an intra-molecular O-H?O hydrogen bond with the carbonyl O atom of the propenone unit, generating an S(5) ring.

SUBMITTER: Hashim NA

PROVIDER: S-EPMC3200863 | biostudies-other | 2011 Sep

REPOSITORIES: biostudies-other

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(E)-3-[3,4-Bis(meth-oxy-methoxy)phen-yl]-1-(7-hy-droxy-5-meth-oxy-2,2-dimethyl-chroman-8-yl)prop-2-en-1-one.

Hashim Nur Athirah NA Ahmad Farediah F Basar Norazah N Awang Khalijah K Ng Seik Weng SW

Acta crystallographica. Section E, Structure reports online 20110811 Pt 9

The reaction of 5,6-(2,2-dimethyl-chroman-yl)-2-hy-droxy-4-meth-oxy-acetophenone and 3,4-bis-(meth-oxy-meth-yloxy)benzaldehyde affords the intense orange title chalcone derivative, C(25)H(30)O(8). The two benzene rings are connected through a -C(=O)-CH=CH- (propenone) unit, which is in an E conformation; the ring with the hy-droxy substitutent is aligned at 19.5 (2)° with respect to this unit, whereas the ring with the meth-oxy-meth-yloxy substituent is aligned at 9.3 (3)°. The dihedral angle be ...[more]

PMID: 22058935

Similar Datasets

(E)-3-(2H-1,3-Benzodioxol-5-yl)-1-(7-hy-droxy-5-meth-oxy-2,2-dimethyl-chroman-8-yl)prop-2-en-1-one.

Project description:The reaction of 5,6-(2,2-dimethyl-chromane)-2-hy-droxy-4-meth-oxy-acetophenone and 3,4-methlene-dioxy-benzaldehyde affords the title chalcone derivative, C(22)H(22)O(6). The two benzene rings are connected through a -C(=O)-CH=CH- (propenone) unit, which is in an E conformation; the ring with the hy-droxy substitutent is aligned at 6.2?(1)° with respect to this unit, whereas the ring with the methyl-enedi-oxy substituent is aligned at 8.2?(1)°. The dihdral angle between the rings is 14.32?(7)°. The hy-droxy group engages in an intra-molecular hydrogen bond with the carbonyl O atom of the propenone unit, generating an S(5) ring.

| S-EPMC3200850 | biostudies-other

(E)-3-(4-Hy-droxy-3-meth-oxy-phen-yl)-1-(4-hy-droxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C16H14O4, there is an intra-molecular O-H⋯O hydrogen bond. The benzene rings are inclined to one another by 13.89 (9)°. The prop-2-en-1-one group is twisted slightly, the O=C-Car-Car (ar = aromatic) and C=C-C=O torsion angles being -10.4 (3) and -7.4 (3)°, respectively. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains along [100]. These chains are further linked by O-H⋯O hydrogen bonds, forming corrugated sheets lying parallel to (010). There are C-H⋯π inter-actions present within the sheets.

| S-EPMC4011235 | biostudies-literature

(E)-1-[2-Hy-droxy-4,6-bis-(meth-oxy-meth-oxy)phen-yl]-3-[3-meth-oxy-4-(meth-oxy-meth-oxy)phen-yl]prop-2-en-1-one.

Project description:The title compound, C(22)H(26)O(9), crystallizes with two independent mol-ecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4 (2) and 5.1 (2)°. An intra-molecular O-H⋯O hydrogen bond occurs in each mol-ecule. Inter-molecular C-H⋯O hydrogen bonds stabilize the crystal structure.

| S-EPMC3247344 | biostudies-literature

Crystal structure of (E)-3-(3,4-di-meth-oxy-phen-yl)-1-(1-hy-droxy-naphthalen-2-yl)prop-2-en-1-one.

Project description:The mol-ecular structure of the title compound, C21H18O4, consists of a 3,4-di-meth-oxy-phenyl ring and a naphthalene ring system linked via a prop-2-en-1-one spacer. The mol-ecule is almost planar, with a dihedral angle between the benzene ring and the naphthalene ring system of 2.68 (12)°. There is an intra-molecular O-H⋯O hydrogen bond involving the adjacent hy-droxy and carbonyl groups. The mol-ecule has an E conformation about the C=C bond and the carbonyl group is syn with respect to the C=C bond. In the crystal, mol-ecules are linked by bifurcated C-H⋯(O,O) hydrogen bonds, enclosing an R 2 (1)(6) ring motif, and by a further C-H⋯O hydrogen bond, forming undulating sheets extending in b- and c-axis directions. There are π-π inter-actions between the sheets, involving inversion-related naphthalene and benzene rings [inter-centroid distance = 3.7452 (17) Å], forming a three-dimensional structure.

| S-EPMC4420054 | biostudies-literature

(E)-1-(2-Hy-droxy-6-meth-oxy-phen-yl)-3-(2,4,6-tri-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C19H20O6, the conformation about the C=C bond of the central enone group is E. The dihedral angle formed by the benzene rings is 11.6 (2)°. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

| S-EPMC3885064 | biostudies-literature

(E)-1-[2-Hy-droxy-4,6-bis-(meth-oxy-meth-oxy)phen-yl]-3-phenyl-prop-2-en-1-one.

Project description:The title compound, C19H20O6, consists of a tetra-substituted benzene ring with one substituent being an α,β-unsaturated cinnamoyl group, which forms an extended conjugated system in the mol-ecule. In addition, two meth-oxy-meth-oxy and one hy-droxy group are bonded to the central benzene ring. The dihedral angle between eh rings is 10.22 (10)°. An intra-molecular hydrogen bond is observed between the hy-droxy group and the carbonyl O atom. One of the meth-oxy-meth-oxy substituents is conformationally disordered over two sets of sites with site-occupation factors of 0.831 (3) and 0.169 (3).

| S-EPMC3648248 | biostudies-literature

(2E)-3-(3,4-Dimeth-oxy-phen-yl)-1-(4-hy-droxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(17)H(16)O(4), the dihedral angle between the mean planes of the hy-droxy-phenyl and dimeth-oxy-phenyl rings is 19.34 (7)°. The mean plane of the prop-2-en-1-one group, the active site in this mol-ecule, makes angles of 7.40 (8) and 13.25 (8)°, respectively, with the hy-droxy-phenyl and dimeth-oxy-phenyl rings. The crystal packing is stabilized by O-H⋯O hydrogen bonds, weak inter-molecular C-H⋯O and π-π stacking inter-actions [centroid-centroid distance = 3.7386 (9) Å].

| S-EPMC3099842 | biostudies-literature

(E)-3-(3,4-Dimeth-oxy-phen-yl)-1-(2-hy-droxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(17)H(16)O(4), the dihedral angle between the mean planes of the hy-droxy-phenyl and dimeth-oxy-phenyl rings is 5.9 (6)°. The mean plane of the prop-2-en-1-one group makes dihedral angles of 3.6 (0) and 2.6 (7)° with the hy-droxy-phenyl and dimeth-oxy-phenyl rings, respectively. An intra-molecular O-H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak inter-molecular C-H⋯O contacts and π-π stacking inter-actions [centroid-centroid distance = 3.6571 (8) Å].

| S-EPMC3099868 | biostudies-literature

Crystal structure of (2E)-1-(4-hy-droxy-3-meth-oxy-phen-yl)-3-(4-hy-droxy-phen-yl)prop-2-en-1-one.

Project description:In the title moleclue, C16H14O4, the dihedral angle between the benzene rings is 16.1 (3)°. The meth-oxy group is essentially coplanar with the benzene ring to which it is attached, with a C-O-C C torsion angle of 5.5 (9)°. In the crystal, mol-ecules are linked by O-H⋯O and bifurcated O-H⋯(O,O) hydrogen bonds, forming a three-dimensional network. The structure was refined as a two-component inversion twin.

| S-EPMC4257319 | biostudies-literature

[(1R,3S)-2,2-Dichloro-3-(hy-droxy-meth-yl)cyclo-prop-yl]methanol.

Project description:The title compound, C(5)H(8)Cl(2)O(2), represents a meso isomer crystallizing in a chiral space group with two mol-ecules per asymmetric unit. The mol-ecules form helical associates with a pitch of 6.31 Å along the a axis via O-H⋯O hydrogen bonds. The overall three-dimesional supra-molecular architecture is stabilized by C-Cl⋯O halogen bonding, with a Cl⋯O separation of 3.139 (3) Å and a C-Cl⋯O angle of 162.5 (2)°.

| S-EPMC3569760 | biostudies-literature

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