Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and structure of photodegradable 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propyl N-butyl-carbamate.

ABSTRACT: The reaction of 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propan-1-ol and butyl-iso-cyanate using di-butyl-tin dilaurate as a catalyst afforded 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propyl N-butyl-carbamate, C₁₇H₂₅N₃O₈, which released butyl-amine upon photoirradiation. Single crystals of the title compound were grown in a 1:1 mixed solution of hexane and ethyl acetate. Two nitro groups and one meth-oxy group are twisted out of the plane of the aromatic ring in the novel photo-protecting group. Inter-molecular hydrogen bonds are observed between N-butyl-carbamate moieties parallel to the a axis.

SUBMITTER: Honda T

PROVIDER: S-EPMC10242739 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and structure of photodegradable 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propyl N-butyl-carbamate.

Honda Takafumi T Ito Michiko M Yamaguchi Kazuo K Kasuga Noriko Chikaraishi NC Sato Hiroyasu H

Acta crystallographica. Section E, Crystallographic communications 20230516 Pt 6

The reaction of 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propan-1-ol and butyl-iso-cyanate using di-butyl-tin dilaurate as a catalyst afforded 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propyl N-butyl-carbamate, C17H25N3O8, which released butyl-amine upon photoirradiation. Single crystals of the title compound were grown in a 1:1 mixed solution of hexane and ethyl acetate. Two nitro groups and one meth-oxy group are twisted out of ...[more]

PMID: 37288466

Similar Datasets

2,3-Dibromo-1-[4-(2,3-dibromo-4,5-di-meth-oxy-benz-yl)-2,5-dimeth-oxy-benz-yl]-4,5-dimeth-oxy-benzene.

Project description:The mol-ecule of the title compound, C(26)H(26)Br(4)O(6), is located around a crystallographic inversion center. The dihedral angle between the central benzene ring and the outer benzene ring is 89.26 (1)°.

| S-EPMC3009213 | biostudies-literature

4,5-Bis(2,4-di-tert-butyl-phen-oxy)phthalonitrile.

Project description:In the title compound, C(36)H(44)N(2)O(2), the dihedral angles between the phthalonitrile ring and the two di-tert-butyl-benzene rings are 68.134 (8) and 70.637 (11)°. The two nitrile groups are almost coplanar with the phthalonitrile ring except for one of the N atoms which deviates from the plane by 0.125 (4) Å. One of the tert-butyl groups is disordered over two orientations, with refined occupancies of 0.814 (6) and 0.186 (6). Intra-molecular C-H⋯O inter-actions stabilize the molecular structure. The crystal packing is stabilized by inter-molecular C-H⋯N inter-actions.

| S-EPMC3051978 | biostudies-literature

4,6-Di-tert-butyl-2,8-dimeth-oxy-dibenzo[b,d]furan.

Project description:In the title compound, C(22)H(28)O(3), the dihedral angle between the benzene rings is 3.47 (13)° and the five-membered furan ring is essentially planar with a largest deviation of 0.0052 (14) Å. The Csp(2)-Csp(2) bond length between the two benzene rings [1.443 (3) Å] is considerably shorter than those between the benzene and tertiary C atoms [1.538 (3) and 1.530 (3) Å], which are sp(2)-sp(3) hybridized. C-H⋯π inter-actions involving the furan and benzene rings are found in the crystal structure.

| S-EPMC3239001 | biostudies-literature

(R*)-Methyl 2-(2,6-dimeth-oxy-3,5-di-nitro-benzamido)-propano-ate.

Project description:In the title mol-ecule, C(13)H(15)N(3)O(9), the nitro groups are tilted with respect to the benzene mean plane by 22.8 (3) and 31.6 (3)°. The meth-oxy groups are in a cis orientation relative to the ring. In the crystal, mol-ecules are linked by strong N-H⋯O hydrogen bonds into C(3) chains along [100].

| S-EPMC3414311 | biostudies-literature

(2-tert-Butyl-3-phenyl-2,3-di-hydro-isoxazole-4,5-di-yl)bis-(phenyl-methanone).

Project description:The phenyl and tert-butyl groups of the title compound, C27H25NO3, exhibit a trans configuration in agreement with the stereochemistry of the Z phenyl-N-tert-butyl-nitrone starting material. The attached carbonyl groups are not coplanar with the neighboring di-hydro-isoxazole ring and the phenyl rings they are bonded to, with torsion angles of 59.26 (8), 17.53 (11), 16.52 (12) and 52.86 (7)°. The dihedral angle between the di-hydro-isoxazole ring and the directly attached phenyl group is 86.86 (8)°. There are two nonclassical inter-molecular C-H⋯O hydrogen-bonding inter-actions that operate together with an inter-molecular C-H⋯π inter-action to form a supramolecular architecture in the crystal system.

| S-EPMC3793779 | biostudies-literature

Packing polymorphism in the crystal structure of 4,5-dimeth-oxy-2-nitro-benzyl acetate.

Project description:The title compound, C11H13NO6, shows two polymorphs, orange and yellow forms, both of which crystallize in the space group P21/c. The mol-ecular structures in the two polymorphs are essentially similar and adopt a planar structure, the maximum deviations for the non-H atoms being 0.1836 (13) and 0.1276 (13) Å, respectively, for the orange and yellow forms. In the orange crystal, mol-ecules are linked by an inter-molecular C-H⋯O inter-action into a helical chain along the b-axis direction. The chains are stacked along the c axis through a π-π inter-action [centroid-centroid distance = 3.6087 (11) Å], forming a layer parallel to the bc plane. In the yellow crystal, mol-ecules are connected through C-H⋯O inter-actions into a sheet structure parallel to (-302). No significant π-π inter-action is observed. The unit-cell volume of the orange crystal is larger than that of the yellow one, and this accounts for the predominant growth of the yellow crystal.

| S-EPMC4420102 | biostudies-literature

2,3-Dimeth-oxy-benzaldehyde azine.

Project description:There are one-and-a-half independent mol-ecules in the asymmetric unit of the title compound, C(18)H(20)N(2)O(4). One mol-ecule is centrosymmetric with the mid-point of the N-N bond located on a center of inversion. In the other, which lies on a general position, the benzene rings are aligned at 21.6 (1)°. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal strcture.

| S-EPMC3051495 | biostudies-literature

Crystal structure of 2,3-dimeth-oxy-N-(4-nitro-phen-yl)benzamide.

Project description:In the title compound, C15H14N2O5, the benzene rings are nearly coplanar, making a dihedral angle of 4.89 (8)°. An intra-molecular N-H⋯O hydrogen bond occurs between the imino and meth-oxy groups. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains propagating along the a-axis direction. π-π stacking is observed between parallel benzene rings of neighbouring chains, the centroid-to-centroid distance being 3.6491 (10) Å. Three-dimensional Hirshfeld surface analyses and two-dimensional fingerprint plots have been used to analyse the inter-molecular inter-actions present in the crystal.

| S-EPMC5778482 | biostudies-literature

2-(4,5-Dimeth-oxy-2-nitro-phen-yl)-4-meth-oxy-3-methyl-9-phenyl-sulfonyl-9H-carbazole.

Project description:In the title compound, C28H24N2O7S, the carbazole system is essentially planar, with a maximum deviation of 0.0644 (19) Å for the C atom connected to the 4,5-dimeth-oxy-2-nitro-phenyl group. The dihedral angle between the carbazole moiety and the dimethoxy-substituted nitrophenyl ring is 58.55 (7)°. The sulfonyl group forms two intra-molecular C-H⋯O bonds with the adjacent carbazole system, forming two cyclic S(6) motifs. In the crystal, mol-ecules are linked along the a axis in bands consisting of cyclic R 3 (3)(15) motifs through two further C-H⋯O hydrogen bonds.

| S-EPMC3998409 | biostudies-literature

2-(4,5-Dimeth-oxy-2-nitro-phen-yl)-4-meth-oxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

Project description:In the title compound, C28H22N2O8S, the carbazole ring system is roughly planar, with a maximum deviation of 0.084 (3) Å for the C atom connected to the 4,5-dimeth-oxy-2-nitro-phenyl ring. The dihedral angle between the carbazole system and the dimeth-oxy-substituted nitro-phenyl ring is 57.05 (10)°. The aldehyde C atom deviates by 0.164 (5) Å from its attached carbazole ring system. The mol-ecular structure is stabilized by C-H⋯O inter-actions which generate two S(6) and one S(7) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming R 3 (3)(15) ring motifs, which are further crosslinked by R 3 (2)(19) ring motifs, resulting in (002) layers. The crystal packing also features C-H⋯π inter-actions.

| S-EPMC3998565 | biostudies-literature