Literature DB >> 26044332

A structural study of (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1,3,5-triphenylcyclohexan-1-ol chloroform hemisolvate and (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1-phenyl-3,5-bis(2-methoxyphenyl)cyclohexan-1-ol.

Mikhail E Minyaev1, Dmitrii M Roitershtein1, Ilya E Nifant'ev1, Ivan V Ananyev2, Tatyana V Minyaeva3, Timofey A Mikhaylyev4.   

Abstract

(1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol or (4-hydroxy-2,4,6-triphenylcyclohexane-1,3-diyl)bis(phenylmethanone), C38H32O3, (1), is formed as a by-product in the NaOH-catalyzed synthesis of 1,3,5-triphenylpentane-1,5-dione from acetophenone and benzaldehyde. Single crystals of the chloroform hemisolvate, C38H32O3·0.5CHCl3, were grown from chloroform. The structure has triclinic (P1) symmetry. One diastereomer [as a pair of (1RS,2SR,3RS,4SR,5RS)-enantiomers] of (1) has been found in the crystal structure and confirmed by NMR studies. The dichoromethane hemisolvate has been reported previously [Zhang et al. (2007). Acta Cryst. E63, o4652]. (1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-3,5-bis(2-methoxyphenyl)-1-phenylcyclohexan-1-ol or [4-hydroxy-2,6-bis(2-methoxyphenyl)-4-phenylcyclohexane-1,3-diyl]bis(phenylmethanone), C40H36O5, (2), is also formed as a by-product, under the same conditions, from acetophenone and 2-methoxybenzaldehyde. Crystals of (2) have been grown from chloroform. The structure has orthorhombic (Pca2₁) symmetry. A diastereomer of (2) possesses the same configuration as (1). In both structures, the cyclohexane ring adopts a chair conformation with all bulky groups (benzoyl, phenyl and 2-methoxyphenyl) in equatorial positions. The molecules of (1) and (2) both display one intramolecular O-H···O hydrogen bond.

Entities:  

Keywords:  NMR analysis; crystal structure; cyclohexanol; diastereomers; hydrogen bonding; triphenylcyclopentadiene synthesis

Year:  2015        PMID: 26044332     DOI: 10.1107/S2053229615009857

Source DB:  PubMed          Journal:  Acta Crystallogr C Struct Chem        ISSN: 2053-2296            Impact factor:   1.172


  2 in total

1.  Synthesis of Terpyridines: Simple Reactions-What Could Possibly Go Wrong?

Authors:  Dalila Rocco; Catherine E Housecroft; Edwin C Constable
Journal:  Molecules       Date:  2019-05-09       Impact factor: 4.411

2.  (1R,2S,4r)-1,2,4-Tri-phenyl-cyclo-pentane-1,2-diol and (1R,2S,4r)-4-(2-meth-oxy-phen-yl)-1,2-di-phenyl-cyclo-pentane-1,2-diol: application as initiators for ring-opening polymerization of ∊-caprolactone.

Authors:  Pavel D Komarov; Mikhail E Minyaev; Andrei V Churakov; Dmitrii M Roitershtein; Ilya E Nifant'ev
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-06-21
  2 in total

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