The cocrystalrac-1-[(N,4-dimethylbenzenesulfonamido)methyl]-2-(diphenylphosphoryl)ferrocene–rac-1-[(N,4-dimethylbenzenesulfonamido)methyl]-2-(diphenylphosphanyl)ferrocene (0.45/0.55)

As part of our interest in the synthesis and catalytic applications of chiral (diphenylphosphanyl)ferrocene ligands, we designed a number of P,N-containing ligands for use in asymmetric transfer hydrogenation (ATH). During the synthetic procedure to obtainrac-1-[(N,4-dimethylbenzenesulfonamido)methyl]-2-(diphenylphosphanyl)ferrocene, the title compound, [Fe(C5H5)(C26H25NO2PS)]0.55·[Fe(C5H5)(C26H25NO3PS)]0.45, was obtained as a by-product. It is composed of a ferrocene group disubstituted by a partially oxidized diphenylphosphanyl group, as confirmed by31P NMR analysis, and an (N,4-dimethylbenzenesulfonamido)methyl substituent. Owing to the partially oxidized diphenylphosphanyl group, it is best to view the crystal as being composed of a mixture of non-oxidized and oxidized phosphane, so it can be regarded as a cocrystal. It is also a racemate. To the best of our knowledge, the P=O distance [1.344 (4) Å] is the shortest observed for related (diphenylphosphoryl)ferrocene compounds. The packing is stabilized by weak C—H...O interactions, formingR22(10) hydrogen-bonding motifs, which build up a chain along thecaxis.

Download Full-text

Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid

Synlett ◽

10.1055/s-0040-1706415 ◽

2020 ◽

Vol 31 (17) ◽

pp. 1735-1739

Author(s):

Narihito Ogawa ◽

Shinsaku Sone ◽

Song Hong ◽

Yan Lu ◽

Yuichi Kobayashi

Keyword(s):

Docosahexaenoic Acid ◽

Title Compound ◽

Wittig Reaction ◽

Transfer Hydrogenation ◽

Sonogashira Coupling ◽

Asymmetric Transfer Hydrogenation ◽

Asymmetric Dihydroxylation

The C16–C22 fragment with the acetylene terminus was constructed through the asymmetric dihydroxylation of the corresponding olefin, while the 15-iodo-olefin corresponding to the C11–C15 part was prepared via the asymmetric transfer hydrogenation of the corresponding acetylene ketone followed by hydrozirconation/iodination. Both pieces were joined by a Sonogashira coupling, and the product was further converted into the title compound via a Wittig reaction with the remaining C1–C10 segment and Boland reduction using Zn with TMSCl.

Download Full-text

Aqua(2,2′-bipyridine-κ2 N,N′)bis(4-formylbenzoato-κ2 O,O′)cadmium(II) monohydrate

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s160053680705115x ◽

2007 ◽

Vol 63 (11) ◽

pp. m2799-m2799 ◽

Cited By ~ 1

Author(s):

Zhao-Peng Deng ◽

Shan Gao ◽

Li-Hua Huo ◽

Hui Zhao

Keyword(s):

Hydrogen Bonding ◽

Water Molecule ◽

Title Compound ◽

Unit Cell ◽

Water Molecules ◽

Solvent Water ◽

Monoclinic Unit Cell ◽

A Chain ◽

Trigonal Prismatic

In the mononuclear title compound, [Cd(C8H5O3)2(C10H8N2)(H2O)]·H2O, the Cd atom is O,O′-chelated by two 4-formylbenzoate monoanions and N,N′-chelated by 2,2′-bipyridine. It is also coordinated by a water molecule in a monocapped trigonal-prismatic geometry. The coordinated and solvent water molecules and O atoms of the monoanions engage in hydrogen bonding, resulting in a chain running along the b axis of the monoclinic unit cell.

Download Full-text

3-(4-Hexyloxyphenyl)isobenzofuran-1(3H)-one

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s1600536806013298 ◽

2006 ◽

Vol 62 (5) ◽

pp. o1941-o1943 ◽

Cited By ~ 1

Author(s):

M. Vijayan ◽

K. Chinnakali ◽

P. Amaladass ◽

A. K. Mohanakrishnan ◽

Hoong-Kun Fun

Keyword(s):

Hydrogen Bonding ◽

Hydrogen Bonds ◽

Title Compound ◽

Ring System ◽

Unit Cell ◽

Axis Direction ◽

Compound C ◽

Hydrogen Bonding Interactions ◽

Ribbon Structure ◽

A Chain

In the title compound, C20H22O3, the hexyloxyphenyl group is orthogonal to the isobenzofuran-1-one ring system. The molecules, translated by one unit cell along the a-axis direction, are linked into a chain by intermolecular C—H...O hydrogen-bonding interactions, and the inversion-related molecules of adjacent chains are linked via C—H...O hydrogen bonds to form a ribbon structure.

Download Full-text

trans-Tetrakis[N-(adamantan-1-yl)pyridine-4-carboxamide]dichloridomanganese(II)–N-(adamantan-1-yl)pyridine-4-carboxamide (1/2)

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s1600536812010124 ◽

2012 ◽

Vol 68 (4) ◽

pp. m408-m408

Author(s):

Ying-Chun Wang

Keyword(s):

Hydrogen Bonding ◽

Title Compound ◽

Organic Ligands ◽

Asymmetric Unit ◽

Hydrogen Bonding Interactions ◽

Distorted Octahedral ◽

A Chain ◽

Cl Atoms

The asymmetric unit of the title compound, [MnCl2(C16H20N2O)4]·2C16H20N2O, is composed of two coordinatingN-(adamantan-1-yl)pyridine-4-carboxamide molecules, one Cl−anion, an MnIIion, lying on an inversion centre, and one freeN-(adamantan-1-yl)pyridine-4-carboxamide molecule. The distorted octahedral Mn environment comprises two terminal Cl atoms and four monodentate N atoms from four organic ligands. All the carbamoyl N atoms are involved in intermolecular N—H...O hydrogen-bonding interactions which link the molecules into a chain along theaaxis.

Download Full-text

The enantioselective synthesis of (S)-(+)-mianserin and (S)-(+)-epinastine

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.11.164 ◽

2015 ◽

Vol 11 ◽

pp. 1509-1513 ◽

Cited By ~ 8

Author(s):

Piotr Roszkowski ◽

Jan K Maurin ◽

Zbigniew Czarnocki

Keyword(s):

Asymmetric Reduction ◽

Enantioselective Synthesis ◽

Pure Form ◽

Transfer Hydrogenation ◽

Asymmetric Transfer Hydrogenation ◽

Synthetic Pathway ◽

Synthetic Procedure ◽

Optically Pure

A simple enantioselective synthetic procedure for the preparation of mianserin and epinastine in optically pure form is described. The key step in the synthetic pathway is the asymmetric reduction of the cyclic imine using asymmetric transfer hydrogenation conditions.

Download Full-text

5-Ethynyl-2′-deoxycytidine: a DNA building block with a `clickable' side chain

Acta Crystallographica Section C Crystal Structure Communications ◽

10.1107/s0108270112038267 ◽

2012 ◽

Vol 68 (10) ◽

pp. o395-o398 ◽

Cited By ~ 2

Author(s):

Frank Seela ◽

Hui Mei ◽

Hai Xiong ◽

Simone Budow ◽

Henning Eickmeier ◽

...

Keyword(s):

Crystal Structure ◽

Hydrogen Bonding ◽

Building Block ◽

Title Compound ◽

Crystalline State ◽

Three Dimensional ◽

Side Chain ◽

Sugar Residue ◽

A Chain ◽

Dimensional Crystal

The title compound [systematic name: 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-ethynylpyrimidin-2(1H)-one], C11H13N3O4, shows two conformations in the crystalline state. The N-glycosylic bonds of both conformers adopt similar conformations, with χ = −149.2 (1)° for conformer (I-1) and −151.4 (1)° for conformer (I-2), both in theantirange. The sugar residue of (I-1) shows a C2′-endoenvelope conformation (2E,S-type), withP= 164.7 (1)° and τm= 36.9 (1)°, while (I-2) shows a major C3′-exosugar pucker (C3′-exo-C2′-endo,3T2,S-type), withP= 189.2 (1)° and τm= 33.3 (1)°. Both conformers participate in the formation of a layered three-dimensional crystal structure with a chain-like arrangement of the conformers. The ethynyl groups do not participate in hydrogen bonding, but are arranged in proximal positions.

Download Full-text

(1S,3R,6S,7R)-3,7-Dichloro-trans-himachalane

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s1600536807008409 ◽

2007 ◽

Vol 63 (3) ◽

pp. o1497-o1499 ◽

Cited By ~ 1

Author(s):

Najia Ourhriss ◽

Noureddine Mazoir ◽

Jean-Claude Daran ◽

Moha Berraho ◽

Ahmed Benharref

Keyword(s):

Hydrogen Bonding ◽

Title Compound ◽

Chair Conformation ◽

Membered Ring ◽

Hydrogen Bonding Interaction ◽

Compound C ◽

Bonding Interaction ◽

A Chain

The molecule of the title compound, C15H26Cl2, is built up from two fused six-membered and seven-membered rings. The six-membered ring has a perfect chair conformation, whereas the seven-membered ring displays a twist-chair conformation. A weak C—H...Cl hydrogen-bonding interaction links the molecule into a chain parallel to the a axis.

Download Full-text