Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers.

نویسندگان

  • D Heulyn Jones
  • Stefano Bresciani
  • James P Tellam
  • Justyna Wojno
  • Anthony W J Cooper
  • Alan R Kennedy
  • Nicholas C O Tomkinson
چکیده

The isomers of dibenzylamino-1-methylcyclohexan-1-ol and dibenzylamino-1-trifluoromethylcyclohexan-1-ol have been prepared. The stereochemistry of these compounds was unequivocally assigned through a combination of NMR spectroscopy and single crystal X-ray analysis. The cis-isomer of 3-N,N-dibenzylamino-1-trifluoromethylcyclohexanol and its derivatives display an unusual conformational behaviour in both solution-phase and the solid-state, where the amino group usually adopts an axial conformation.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol.

The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

متن کامل

1-Dibenzylamino-1-de­oxy-4,5-O-isopropyl­idene-β-d-fructopyran­ose

The title compound C(23)H(29)NO(5), synthesized by the Amadori rearrangement of α-d-glucose with dibenzyl-amine and the ketalization, is shown to be a β-anomer. The fructopyran-ose ring adopts a chair conformation. The two benzene rings form a dihedral angle of 68.9 (1)°. In the crystal, non-classical inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

متن کامل

Regio- and stereoselective synthesis of new diaminocyclopentanols

The optimal conditions for regio- and stereoselective epoxide ring opening of N,N-disubstituted 1,2-epoxy-3-aminocyclopentanes by different nucleophilic reagents have been developed. The substituents on the nitrogen atom in the epoxide precursor and the orientation of the oxirane ring are crucial for the reaction outcome. Thus, treatment of (1RS,2SR,3SR)-1,2-epoxy-3-(N,N-dibenzylamino)cyclopent...

متن کامل

Stereochemical Aspects of the Metabolism of the Isomeric Methylcyclohexanols and Methylcyclohexanones.

1. The seven isomeric optically inactive forms of methylcyclohexanol (i.e. 1-, and cis- and trans-2-, -3- and -4-) are excreted by rabbits mainly as glucuronides of the thermodynamically more stable forms of the alcohols. The eighth isomer, cyclohexylmethanol, however, undergoes aromatization in vivo, giving rise to benzoic acid and hippuric acid. The (+/-)-2-, (+/--3- and 4-methylcyclohexanone...

متن کامل

Diverse reactivity of an isolable dialkylsilylene toward imines.

The reactions of isolable dialkylsilylene 10 with various aldimines proceed smoothly at low temperatures to give diverse products depending on the substituents on the imine. The reactions of 10 with 4-XC(6)H(4)CH=NPh [X = H (11a), MeO (11b), and Cl (11c)] give the corresponding silaaziridines 12a-12c in high yields, which are thermally very stable and remain intact in the air and moisture for a...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 14 1  شماره 

صفحات  -

تاریخ انتشار 2016