scholarly journals Crystal structure of (E)-13-{4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}parthenolide methanol hemisolvate

2014 ◽  
Vol 70 (10) ◽  
pp. o1092-o1093 ◽  
Author(s):  
Narsimha Reddy Penthala ◽  
Shobanbabu Bommagani ◽  
Venumadhav Janganati ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Title Compound ◽  
Heck Reaction ◽  
Lactone Ring ◽  
Phenyl Group ◽  
Exocyclic Double Bond ◽  
Reaction Conditions ◽  
Compound C ◽  
Methyl Phenyl

The title compound, C33H35NO6[systematic name: (Z)-3-(4-{(E)-[(E)-1a,5-dimethyl-9-oxo-2,3,7,7a-tetrahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-8(1aH,6H,9H,10aH,10bH)-ylidene]methyl}phenyl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile methanol hemisolvate], C33H35NO6·0.5CH3OH, was prepared by the reaction of (Z)-3-(4-iodophenyl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile with parthenolide [systematic name: (E)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one] under Heck reaction conditions. The molecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a {4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}methylidene group as a substituent. The 4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl group on the parthenolide exocyclic double bond is oriented in atransposition to the lactone ring to form theEisomer. The dihedral angle between the benzene ring of the phenyl moiety and the lactone ring mean plane is 21.93 (4)°.

scholarly journals Crystal structure of (E)-13-(pyrimidin-5-yl)parthenolide

2015 ◽  
Vol 71 (12) ◽  
pp. 1536-1538 ◽  
Author(s):  
Shobanbabu Bommagani ◽  
Narsimha R. Penthala ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Crystal Structure ◽  
Title Compound ◽  
Heck Reaction ◽  
Lactone Ring ◽  
Chair Conformation ◽  
Ring System ◽  
Membered Ring ◽  
Reaction Conditions ◽  
Compound C ◽  
Pyrimidine Moiety

The title compound, C19H22N2O3, {systematic name (1aR,4E,7aS,8E,10aS,10bR)-1a,5-dimethyl-8-[(pyrimidin-5-yl)methylidene]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one} was obtained from the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bR,E)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one] with 5-bromopyrimidine under Heck reaction conditions, and was identified as anEisomer. The molecule possesses ten-, five- (lactone) and three-membered (epoxide) rings with a pyrimidine group as a substituent. The ten-membered ring displays an approximate chair–chair conformation, while the lactone ring shows a flattened envelope-type conformation. The dihedral angle between the pyrimidine moiety and the lactone ring system is 29.43 (7)°.

scholarly journals Crystal structure of 13-(E)-(2-aminobenzylidene)parthenolide

2018 ◽  
Vol 74 (11) ◽  
pp. 1543-1546
Author(s):  
Shobanbabu Bommagani ◽  
Narsihma R. Penthala ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Heck Reaction ◽  
Lactone Ring ◽  
Chair Conformation ◽  
Membered Ring ◽  
Reaction Conditions ◽  
Compound C

The title compound, C21H25NO3[systematic name: (1aR,4E,7aS,8E,10aS,10bR)-8-(2-aminobenzylidene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one], was synthesized by the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bS,E)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one] with 2-iodoanilineviaHeck reaction conditions. The molecule is composed of fused ten-, five- (lactone), and three-membered (epoxide) rings. The lactone ring shows a flattened envelope-type conformation (r.m.s. deviation from planarity = 0.0477 Å), and bears a 2-aminobenzylidene substituent that is disordered over two conformations [occupancy factors 0.901 (4) and 0.099 (4)]. The ten-membered ring has an approximate chair–chair conformation. The dihedral angle between the 2-aminobenzylidine moiety (major component) and the lactone ring (mean plane) is 59.93 (7)°. There are no conventional hydrogen bonds, but there are a number of weaker C—H...O-type interactions.

scholarly journals (E)-13-(2-Bromophenyl)micheliolide

2014 ◽  
Vol 70 (3) ◽  
pp. o251-o252
Author(s):  
Narsimha Reddy Penthala ◽  
Shobanbabu Bommagani ◽  
Venumadhav Janganati ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Hydrogen Bonding ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Heck Reaction ◽  
Lactone Ring ◽  
Reaction Conditions ◽  
Compound C ◽  
The Mean ◽  
Graph Set

The title compound, C21H23BrO3[systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O—H...O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motifS(6). The 2-bromophenyl group istransto the lactone ring, indicating that this is theEisomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.

scholarly journals Crystal structure of a bioactive sesquiterpene isolated fromArtemisia reticulata

2016 ◽  
Vol 72 (4) ◽  
pp. 460-462
Author(s):  
A. K. Bauri ◽  
Sabine Foro ◽  
Nhu Quynh Nguyen Do
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Hydrogen Bonds ◽  
Silica Gel ◽  
Title Compound ◽  
Chair Conformation ◽  
Cyclohexane Ring ◽  
Exocyclic Double Bond ◽  
Compound C ◽  
Cyclopentane Ring

The title compound, C15H24O2{systematic name: 1-[6-hydroxy-7-(propan-2-yl)-4-methylidene-2,3,3a,4,5,6,7,7a-octahydro-1H-inden-1-yl]ethanone} was isolated fromA. reticulataby column chromatography over silica gel by gradient solvent elution. The molecule comprises a bicyclo[4.3.0]nonane ring bearing acetoxy, hydroxy and isopropyl substituents, and an exocyclic double bond on the cyclohexane ring. In the bicyclic skeleton, the cyclohexane ring adopts a chair conformation ring and the cyclopentane ring is in an envelope conformation. In the crystal, molecules are linked by O—H...O hydrogen bonds, forming chains along [010]. These chains are cross-linked by C—H...O hydrogen bonds.

scholarly journals Crystal structure of (3E)-3-[(4-nitrophenoxy)methyl]-4-phenylbut-3-en-2-one

2014 ◽  
Vol 70 (9) ◽  
pp. o1020-o1021 ◽  
Author(s):  
Julio Zukerman-Schpector ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Paulo R. Nucci ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Torsion Angle ◽  
Title Compound ◽  
Crystal Packing ◽  
Phenyl Group ◽  
Aromatic Rings ◽  
Compound C ◽  
Centroid Distance ◽  
Phenyl Rings

In the title compound, C17H15NO4, the conformation about the C=C double bond [1.348 (2) Å] isEwith the ketone group almost co-planar [C—C—C—C torsion angle = 7.2 (2)°] but the phenyl group twisted away [C—C—C—C = 160.93 (17)°]. The terminal aromatic rings are almost perpendicular to each other [dihedral angle = 81.61 (9)°] giving the molecule an overall U-shape. The crystal packing feature benzene-C—H...O(ketone) contacts that lead to supramolecular helical chains along thebaxis. These are connected by π–π interactions between benzene and phenyl rings [inter-centroid distance = 3.6648 (14) Å], resulting in the formation of a supramolecular layer in thebcplane.

scholarly journals Crystal structure of (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one

2014 ◽  
Vol 70 (9) ◽  
pp. o1051-o1052 ◽  
Author(s):  
Ignez Caracelli ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Felix N. Delling ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Nitro Group ◽  
Benzene Ring ◽  
Torsion Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Aromatic Rings ◽  
Compound C ◽  
The One

In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] isE, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in theorthoposition is twisted [O—N—C—C = 138.28 (13)°]. The molecules associateviaC—H...O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N...O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].

scholarly journals Methyl 1-[(Z)-2-(benzyloxycarbonyl)hydrazin-1-ylidene]-5-chloro-2-hydroxyindane-2-carboxylate

2014 ◽  
Vol 70 (5) ◽  
pp. o527-o527
Author(s):  
Kun Dong ◽  
Yifeng Wang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Double Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Compound C ◽  
Important Intermediate

The title compound, C19H17ClN2O5, is an important intermediate for the synthesis of the pesticide Indoxacarb [systematic name: (S)-methyl 7-chloro-2-{[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl}-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate] The C=N double bond has aZconformation. An intramolecular N—H...O hydrogen bond occurs. In the crystal structure, O—H...O hydrogen bonds result in the formation of 12-membered rings lying about inversion centers withR44(12) motifs.

scholarly journals Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

2017 ◽  
Vol 73 (3) ◽  
pp. 407-409
Author(s):  
Adailton J. Bortoluzzi ◽  
Gustavo P. Silveira ◽  
Marcus M. Sá
Keyword(s):  
Crystal Structure ◽  
Benzene Ring ◽  
Absolute Configuration ◽  
Title Compound ◽  
Benzoyl Chloride ◽  
Lactone Ring ◽  
Three Dimensional ◽  
Acylation Reaction ◽  
Compound C ◽  
Dimensional Network

In the title compound, C15H16O6, obtained from the acylation reaction between 2,3-O-isopropylidene-D-ribono-1,4-lactone and benzoyl chloride, the known absolute configuration for the lactone moiety of the ester substituent has been confirmed. The five-membered rings of the bicyclic lactone–dioxolane moiety both show envelope conformations and form a dihedral angle of 19.82 (7)° between the lactone ring and the benzene ring. In the crystal, molecules of the acylated sugar are linked by very weak intermolecular C—H...O interactions, forming a three-dimensional network.

scholarly journals Crystal structure of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1-oxide

2017 ◽  
Vol 73 (8) ◽  
pp. 1189-1191 ◽  
Author(s):  
Hemant P. Yennawar ◽  
Ryan Fox ◽  
Quentin J. Moyer ◽  
Ziwei Yang ◽  
Lee J. Silverberg
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Benzene Ring ◽  
Title Compound ◽  
Phenyl Group ◽  
Dihedral Angles ◽  
Compound C ◽  
Hydrogen Bonding Interactions ◽  
Thiazine Ring

In the racemic title compound, C20H15NO2S, the planes of the two phenyl substituents form dihedral angles of 48.97 (15) and 69.26 (15)° with that of the fused benzene ring of the parent benzothiazine ring, while the heterocyclic thiazine ring exhibits a screw-boat pucker. The O atom on the S atom of the ring is pseudo-axial on the thiazine ring and trans to the 2-phenyl group. In the crystal, molecules are arranged in layers in the ac plane, the layers being linked across b through intermolecular C—H...O hydrogen-bonding interactions.

scholarly journals Crystal structure of (Z)-3-[5-chloro-2-(prop-2-ynyloxy)phenyl]-3-hydroxy-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one

2015 ◽  
Vol 71 (8) ◽  
pp. o556-o557
Author(s):  
Aarti Dalal ◽  
Ramesh C. Kamboj ◽  
Dinesh Kumar ◽  
Mahendra Kumar Sharma ◽  
Nagendran Selvarajan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Double Bond ◽  
Dihedral Angle ◽  
Title Compound ◽  
Photochemical Transformation ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Benzene Rings

The title compound, C19H12ClF3O3, obtained by the photochemical transformation of 2-[5-chloro-2-(prop-2-ynyloxy)benzoyl]-3-[4-(trifluoromethyl)phenyl]oxirane adopts aZconformation with respect to the enolic C=C double bond. The dihedral angle between the benzene rings is 12.25 (16)° and an intramolecular O—H...O hydrogen bond closes anS(6) ring. An intramolecular C—H...O interaction also leads to anS(6) ring. In the crystal, very weak C—H...O interactions and short Cl...Cl contacts [3.3221 (16) Å] are seen, as well as weak aromatic π–π stacking interactions [centroid–centroid separation = 3.879 (2) Å].

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