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Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate.

ABSTRACT: The title compound, C(39)H(37)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.61?(5)° between the two carboxyl-ate groups. The crystal packing is stabilized by the weak C-H?O hydrogen bonds.

SUBMITTER: Anh le T

PROVIDER: S-EPMC3344514 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate.

Anh Le Tuan le T Hieu Truong Hong TH Soldatenkov Anatoly T AT Soldatova Svetlana A SA Khrustalev Victor N VN

Acta crystallographica. Section E, Structure reports online 20120413 Pt 5

The title compound, C(39)H(37)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.61 (5)° between the two carboxyl-ate groups. The crystal packing is stabilized by the weak C-H⋯O hydrogen bonds. ...[more]

PMID: 22590276

Similar Datasets

(1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hy-droxy-22,24-diphenyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate.

Project description:The title compound, C40H41NO8, is a product of the reduction of the cyclic carbonyl group of the γ-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The aza-crown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82 (5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethyl-enedi-carboxyl-ate fragment has a cis conformation, with a dihedral angle of 66.51 (7)° between the two carboxyl-ate groups. The ethyl group is disordered over two sites with occupancies of 0.70 (1):0.30 (1). In the crystal, mol-ecules form inversion dimers, via pairs of O-H⋯O hydrogen bonds, that stack along the a axis.

| S-EPMC3772461 | biostudies-literature

Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate.

Project description:The title compound, C(29)H(33)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of the aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation, and the dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 78.96?(5)° between the two carboxyl-ate groups. The crystal packing is stabilized by weak C-H?O hydrogen bonds.

| S-EPMC3379201 | biostudies-other

Crystal structure of 22,24,25-trimethyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.02,7.015,20]penta-cosa-2,4,6,15(20),16,18-hexaen-23-one.

Project description:The title compound, C24H29NO4, is the product of a Petrenko-Kritchenko condensation of 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane, pentan-3-one and methyl-ammonium acetate in ethanol. The mol-ecule has mirror symmetry. The aza-14-crown-3 ether ring adopts a bowl conformation stabilized by a weak intra-molecular C-H⋯O hydrogen bond. The conformation of the C-O-C-C-O-C-C-O-C polyether chain is t-g+-t-t-g--t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether moiety is 72.68 (4)°. The piperidinone ring adopts a chair conformation. The nitro-gen atom has a trigonal-pyramidal geometry, the sum of the bond angles being 335.9°. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions, forming zigzag chains propagating along the [100] direction.

| S-EPMC5290547 | biostudies-literature

24-Acetyl-8,11,14-trioxa-24,27-diaza-penta-cyclo-[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexaen-28-one.

Project description:The title compound, C(25)H(28)N(2)O(5), is a product of the Petrenko-Kritchenko condensation of N-acetyl-piperidone with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a fused penta-cyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intra-molecular N-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into chains along [010].

| S-EPMC3393972 | biostudies-literature

Dimethyl 2-[24-acetyl-28-oxo-8,11,14-trioxa-24,27-diaza-penta-cyclo-[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexaen-27-yl]but-2-enedioate.

Project description:The title compound, C(31)H(34)N(2)O(9), is a product of the Michael addition of the cyclic secondary amine subunit of the (bis-pidino)aza-14-crown-4 ether to dimethyl acetyl-ene-dicarboxyl-ate. The mol-ecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14?(5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.56?(7)° between the two carboxyl-ate groups. The crystal packing is stabilized by weak C-H?O hydrogen bonds.

| S-EPMC3414347 | biostudies-literature

meso-(1S*,21R*)-25-Methyl-8,11,14-trioxa-22,24,25-triaza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexa-ene-23-thione chloro-form monosolvate.

Project description:The title compound crystallizes as a chloro-form solvate, C(20)H(23)N(3)O(3)S·CHCl(3), with two crystallographically independent units. The independent units have distinctly different inter-action patterns between the aza-crown macrocycle and the chloro-form solvent mol-ecule. In one of them, the chloro-form mol-ecule forms C-H?N and Cl?H-C hydrogen bonds with the aza-crown macrocycle (as a proton donor and an acceptor, respectively), whereas in the other, one of the chloro-form mol-ecules is bound to the aza-crown macrocycle by an attractive Cl?O [3.080?(3)?Å] inter-action. The aza-crown macrocycles of different units are structurally similar; the aza-14-crown-3-ether ring adopts a bowl conformation with dihedral angles between the planes of the fused benzene rings of 60.7?(1) and 68.0?(1)°. The triazinane-thione ring in both cases has a sofa conformation. The crystal packing is characterized by N-H?S, N-H?O, C-H?Cl and C-H?S hydrogen bonds.

| S-EPMC3470208 | biostudies-literature

Crystal structure of (1RS,21SR,22RS,24SR)-28-oxo-24-propyl-8,11,14-trioxa-24,27-di-aza-penta-cyclo[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexa-ene acetic acid monosolvate.

Project description:The title compound, C26H32N2O4(M)·C2H4O2, (I), is the product of the Petrenko-Kritchenko condensation of N-propyl-piperidinone with 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane and ammonium acetate. In M, the aza-14-crown-3-ether ring adopts a bowl conformation, with the configuration of the C-O-C-C -O-C-C-O-C polyether chain being t-g ((-))-t-t-g ((+))-t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 62.75 (5)°. The central piperidinone ring has a boat conformation, whereas the terminal piperidinone ring adopts a chair conformation. The boat conformation of the central piperidinone ring is supported by the bifurcated intra-molecular N-H⋯O hydrogen bond. In the crystal, each solvent mol-ecule is linked to mol-ecule M via strong O-H⋯N hydrogen bonding, forming hydrogen-bonded pairs of mol-ecules, which further inter-act through weak C-H⋯O hydrogen bonds, forming layers parallel to the ac plane.

| S-EPMC4908554 | biostudies-literature

One-pot synthesis of (1RS,21SR)-diethyl 2-[23-amino-22-eth-oxy-carbonyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.02,7.015,20]penta-cosa-2,4,6,15(20),16,18,22-heptaen-25-yl]but-2-endioate.

Project description:The title compound, C30H34N2O9 (4), is a product of the Michael reaction of aza-crown ether with dimethyl acetyl-enedi-carboxyl-ate modified by an addition of NH3 (aq.) at 298 K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65 (5)°. The tetra-hydro-pyridine ring has a boat conformation. The mol-ecular conformation is supported by one N-H⋯O and two C-H⋯O intra-molecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enanti-omeric pairs of the 1R,21S diastereomer. In the crystal, mol-ecules of 4 are connected by N-H⋯O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit anti-allergic (72% probability) and anti-asthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).

| S-EPMC6127715 | biostudies-literature

Ethyl 23-benzyl-8,11,14-trioxa-23,28,29-triaza-penta-cyclo-[19.7.1.0(2,7).0(15,20).0(22,27)]nona-cosa-2,4,6,15(20),16,18,21,26-octa-ene-26-carboxyl-ate.

Project description:The title compound, C33H35N3O5, is the product of the multicomponent condensation of 1-benzyl-4-eth-oxy-carbonyl-piperidin-3-one with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a penta-cyclic system containing the aza-14-crown-4-ether macrocycle, tetra-hydro-pyrimidine, tetra-hydro-pyridine and two benzene rings. The aza-14-crown-4-ether ring adopts a bowl conformation with a dihedral angle of 62.37 (5)° between the benzene rings. The tetra-hydro-pyrimidine ring has an envelope conformation with the chiral C atom as the flap, whereas the tetra-hydro-pyridine ring adopts a distorted chair conformation. Two amino groups are involved in intra-molecular N-H⋯O hydrogen bonds. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane.

| S-EPMC3629615 | biostudies-literature

3,22-Dioxa-11,14-di-aza-penta-cyclo-[12.8.0.0(2,11).0(5,10).0(15,20)]docosa-5(10),6,8,15(20),16,18-hexa-ene-4,21-dione.

Project description:In the title compound, C18H14N2O4, the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.09?(9)°. In the crystal, mol-ecules are linked along the c axis by C-H?? and N?? [H(N)-centroid distances = 2.8030?(2) and 3.376?(2)?Å] inter-actions between neighbouring mol-ecules.

| S-EPMC3790403 | biostudies-literature

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