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 Crystal structure of 2-amino-N-(2-fluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

2015 ◽  
Vol 71 (11) ◽  
pp. o807-o808
Author(s):  
K. Chandra Kumar ◽  
V. Umesh ◽  
T. K. Madhura ◽  
B. M. Rajesh ◽  
Chandra
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Molecular Conformation ◽  
Chair Conformation ◽  
Ring System ◽  
Membered Ring ◽  
Compound C

In the title compound, C15H15FN2OS, the dihedral angle between the planes of the benzothiophene ring system and the fluorobenzene ring is 3.74 (14)°. The six-membered ring of the benzothiophene moiety adopts a half-chair conformation. The molecular conformation is consolidated by intramolecular N—H...F and N—H...O hydrogen bonds. In the crystal, molecules are linked by N—H...O hydrogen bonds, generatingC(6) [001] chains.

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)-1-{2-[(5,5-dimethyl-1,3,2-dioxaphosphinan-2-yl)oxy]naphthalen-1-yl}-N-(4-fluorophenyl)methanimine

2015 ◽  
Vol 71 (1) ◽  
pp. 85-87
Author(s):  
Musa A. Said ◽  
Bayan L. Al Belewi ◽  
David L. Hughes
Keyword(s):  
Crystal Structure ◽  
Title Compound ◽  
Chair Conformation ◽  
Ring System ◽  
Membered Ring ◽  
Naphthalene Ring ◽  
Π Interactions ◽  
Compound C

In the title compound, C22H21FNO3P, a 1,3,2-dioxaphosphinan-2-yloxy derivative, three O atoms are bonded in a trigonal–pyramidal manner to the P atom. The exocyclic P—O bond is significantly longer than the two endocyclic P—O bonds,viz.1.6678 (12) Å compared to 1.6046 (13) and 1.6096 (12) Å. The six-membered ring which includes the P atom has a chair conformation. The fluorophenyl ring is inclined to the naphthalene ring system by 24.42 (7)°. In the crystal, molecules are linkedviaC—H...π interactions, forming slabs lying parallel to (10-1).

scholarly journals (E)-13-(4-Aminophenyl)parthenolide

2013 ◽  
Vol 69 (11) ◽  
pp. o1709-o1710 ◽  
Author(s):  
Narsimha Reddy Penthala ◽  
Venumadhav Janganati ◽  
Sean Parkin ◽  
Kottayil I. Varughese ◽  
Peter A. Crooks
Keyword(s):  
Heck Reaction ◽  
Lactone Ring ◽  
Resonance Scattering ◽  
Chair Conformation ◽  
Membered Ring ◽  
Epoxide Ring ◽  
Reaction Conditions ◽  
Compound C ◽  
Dimensional Network ◽  
Absolute Structure

The title compound, C21H25NO3[systematic name: (3aS,9aR,10aR,10bS,E)-3-[(E)-4-(4-aminobenzylidene)-6,9a-dimethyl-3a,4,5,8,9,9a,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-2(3H)-one] was obtained from the reaction of parthenolide [synonym: 4,5-epoxygermacra-1(10),11(13)-dieno-12,6-lactone] with 4-iodoaniline under Heck reaction conditions. It was identified as theE-isomer (conformation about the exocyclic methylidene C=C bond; the conformation about the C=C bond in the ten-membered ring is alsoE). The molecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a 4-aminophenyl group as a substituent. The ten-membered ring displays an approximate chair–chair conformation, while the lactone ring has an envelope conformation with the C atom bonded to the ring O atom as the flap. The dihedral angle between the benzene ring of the 4-aminophenyl moiety and the lactone ring mean plane is 23.50 (8)°. In the crystal, molecules are linkedviaN—H...O hydrogen bonds, between the amine group and the lactone and epoxide ring O atoms, forming chains propagating along theb-axis direction. Adjacent chains are linkedviaC—H...O interactions, forming an undulating two-dimensional network lying parallel to the plane (001). The absolute structure of the molecule in the crystal was confirmed by resonance scattering [Flack parameter = 0.03 (3)].

scholarly journals Crystal structure of 7,7-dimethyl-6-methylidenetricyclo[6.2.1.01,5]undecane-2-carboxylic acid

2015 ◽  
Vol 71 (2) ◽  
pp. o94-o94
Author(s):  
Noureddine Beghidja ◽  
Samir Benayache ◽  
Fadila Benayache ◽  
David W. Knight ◽  
Benson M. Kariuki
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Rotation Axis ◽  
Chair Conformation ◽  
Membered Ring ◽  
Envelope Conformation ◽  
Compound C ◽  
Carboxylic Groups

In the title compound, C15H22O2, both five-membered rings display an envelope conformation whereas the six-membered ring displays a chair conformation. In the crystal, pairs of O—H...O hydrogen bonds between carboxylic groups link molecules, related by a twofold rotation axis, into supramolecular dimers.

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 oftrans-1-{2-[4-(dimethylamino)phenyl]ethyl}-4-[2-(pyren-1-yl)ethyl]cyclohexane

2015 ◽  
Vol 71 (8) ◽  
pp. o629-o630
Author(s):  
Sreevidya Thekku Veedu ◽  
Simone Techert
Keyword(s):  
Crystal Structure ◽  
Benzene Ring ◽  
Title Compound ◽  
Chair Conformation ◽  
Ring System ◽  
Maximum Deviation ◽  
Π Interactions ◽  
Twin Domain ◽  
Compound C ◽  
The Mean

The title compound, C34H37N, is a pyrene derivative in which the pyrene ring system is linked to an ethylcyclohexane unit which, in turn, carries a [4-(dimethylamino)phenyl]ethyl substituent in theparaposition. The central cyclohexane ring has a chair conformation, with the exocyclic C—C bonds in equatorial orientations. The benzene ring is inclined to the mean plane of the pyrene ring system [maximum deviation = 0.038 (4) Å] by 14.84 (15)°. In the crystal, molecules are linked by C—H...π interactions, forming chains propagating along [010]. The crystal was refined as a non-merohedral twin [domain ratio = 0.9989 (4):0.0011 (4)].

scholarly journals 4-Benzyloxy-1-oxaspiro[4.6]undec-3-en-2-one

IUCrData ◽  
2016 ◽  
Vol 1 (10) ◽  
Author(s):  
Jose H. Quintana Mendoza ◽  
J. A. Henao ◽  
Elvis Robles Marin ◽  
Juan Manuel Urbina Gonzalez
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Phenyl Ring ◽  
Chair Conformation ◽  
Membered Ring ◽  
Compound C

The title compound, C17H20O3, the cycloheptane ring adopts a slightly distorted chair conformation. The planar five-membered ring is inclined at 57.13 (11)° to the phenyl ring of the benzyloxy substituent. In the crystal structure, C—H...O and C—H...π hydrogen bonds generate layers in the ac plane.

scholarly journals Crystal structure of (1S,2R,4R,9S,11S,12R)-9α-hydroxy-4,8-dimethyl-12-[(thiomorpholin-4-yl)methyl]-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

2015 ◽  
Vol 71 (2) ◽  
pp. o140-o141
Author(s):  
Ahmed Benharref ◽  
Mohamed Akssira ◽  
Lahcen El Ammari ◽  
Mohamed Saadi ◽  
Moha Berraho
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Chair Conformation ◽  
Chloroform Extract ◽  
Ring System ◽  
Membered Ring ◽  
Epoxy Ring ◽  
Aerial Parts ◽  
Compound C ◽  
Hydrogen Bonding Interactions

The title compound, C19H29NO4S, was synthesised from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of the plantAnvillea radiata. The molecule is built up from two fused five- and ten-membered rings, with an additional epoxy ring system and a thiomorpholine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the thiomorpholine ring displays a chair conformation and the five-membered ring has an envelope conformation, with the C atom closest to the hydroxy group forming the flap. An intramolecular O—H...N hydrogen bond closes anS(8) ring. The crystal structure features weak C—H...O hydrogen-bonding interactions, which link the molecules into [010] chains.

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