3,5,7-Tripropyl-1-azaadamantane-4,6,10-triol

Abstract

The title compound, C18H33NO3, was prepared according to a highly diastereoselective hydrogenation procedure from 3,5,7-triallyl-1-aza­adamantane-4,6,10-trione. The crystal structure of the title compound contains two crystallographically independent mol­ecules (Z′ = 2), which are linked by inter­molecular hydrogen bonding into chains. In contrast to the aza­adamantanones, the aza­adamantanetriol core of the title compound does not show any particular C—C bond elongation.

Redetermination of 1,3-diammonio-1,2,3-trideoxy-cis-inositol dichloride

“…The crystal structure of 1,3-diammonio-1,2,3-trideoxy-cis-inositol sulfate has been reported by Neis et al (2012). The importance of intramolecular hydrogen bonding in 1,3,5-trisubstituted cyclohexane derivatives has been described by Gencheva et al (2000), Saaidi et al (2008) and Neis et al (2010), and the implication of increased 1,3-diaxial repulsion on the conformation of a cyclohexane ring has been discussed by Fritsche-Lang et al (1985), Kramer et al (1998) and Kuppert et al (2006). For the synthesis, see: Merten et al (2012).…”

“…As already noted by Palm (1967), the cyclohexane rings of both cations adopt a chair conformation, having one hydroxy and two ammonium groups in equatorial and two hydroxy groups in axial position. triaxial arrangement, a different behaviour has frequently been noted (Gencheva et al, 2000;Saaidi et al, 2008;Neis et al, 2010). If a third syn-axial substituent is present, it appears that formation of such intramolecular hydrogen bonds is sometimes even a prerequisite for the adoption of a stable cyclohexane chair.…”

Solid state supramolecular assemblies of triol podands through H-bonds

“…12 The single crystal X-ray diffraction-based investigations of the lattice of some polycyclitols (tetra and hexahydroxydecalines X and XI and tetrahydroxyperhydroanthracene XII, Chart 2) revealed H-bonding linear structures, which in some cases are bifurcated, generating cyclic entities in the chains; 13 while the investigation of the lattice of 1-azaadamantane-4,6,10-triol (XIII) showed the formation of catemers via intermolecular H-bonds (O-H/N). 14 Similar studies on trigonal rigid triphenols (XIV, Chart 2) pointed out the Hbonding formation of large cavities filled with 18-crown-6 molecules which were included in the lattice during a multicomponent crystallization process. 15 The intermolecular H-bonding in 1,3,5-trihydroxybenzene 16 lead to the disposition of the molecules into two sets of parallel planes (the planes of different sets are almost perpendicular; a ¼ 81.80 ) and to zig-zag arrangements of the connected molecules.…”