72242-49-0Relevant academic research and scientific papers
Diastereoselective Synthesis of Cyclic Five-Membered trans,trans-Configured Nitrodiols by Double Henry Reaction of 1,4-Dialdehydes
Fr?hlich, Janine,Lehmkuhl, Kirstin,Fr?hlich, Roland,Wünsch, Bernhard
, p. 589 - 594 (2015/08/11)
Conformationally constrained perhydroquinoxalines 4 show high κ receptor affinity, selectivity over related receptors and full agonistic activity. Since the κ affinity can be correlated with the dihedral angle of the ethylenediamine pharmacophore (4a: 55°/71°), the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. The first step of the synthesis represents a double Henry reaction of 1,4-dialdehydes 8 and 10 with nitromethane, leading predominantly to the trans,trans-configured nitrodiols 9 and 11. X-ray crystal structure analyses of 9 and 11 led to dihedral angles O2N-C-C-OH of 73.4 and 88.3°, respectively, which reflect the calculated dihedral angles of the hypothesized final products 5a and 6a. Since κ receptor affinity can be correlated with the dihedral angle of ethylenediamine pharmacophores, the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. X-ray crystal structure analyses of the synthesized compounds 9 and 11 led to dihedral angles of 73.4 and 88.3°, respectively, reflecting the calculated dihedral angles of the hypothesized final products 5a and 6a.
The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes
Fleming, Ian,Lawrence, Nicholas J.
, p. 3309 - 3326 (2007/10/02)
The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron
ON THE SYNTHESIS AND CONFORMATIONAL ASPECTS OF 2-METHYL AND 2-t.BUTYL SUBSTITUTED 1,3-CYCLOPENTANE AND CYCLOHEXANE DIOLS
D'Haenens, L.,Sande, C. C. Van de,Tavernier, D.,Vandewalle, M.
, p. 273 - 282 (2007/10/02)
The diastereomers of 2-methyl-1,3-cyclopentanediol, 2-t.butyl-1,3-cyclopentanediol, 2-methyl-1,3-cyclohexanediol and 2-t.butyl-1,3-cyclohexanediol have been prepared.Configurational assignment and some conformational aspects are described.
