NMR Characterization and Crystal Structure of 22-Phenyl-3 beta-acetoxy-bisnorchol-5-en-22-one

作者：Mayorquin Torres Martha C; Flores Alamo Marcos; Iglesias Arteaga Martin A^*

来源：Journal of Chemical Crystallography, 2014, 44(10): 501-505.

DOI：10.1007/s10870-014-0539-x

• Palladium catalyzed cross coupling
• Steroidal phenyl ketone
• X-ray diffraction
• NMR assignments

Palladium catalyzed cross coupling between 3b-acetoxy-bisnorchol-5-en-22-oic acid and phenylboronic acid produced the hereto unknown 22-phenyl-3 beta-acetoxy-bisnorchol-5-en-22-one which crystallizes in the monoclinic system with space group P2(1). The presence of 17 beta-substituent that bears both the C21 methyl group and the introduced phenylketone moiety provides a twisted conformation on C13-C14 for the D ring with asymmetry parameters (Altona et al., Tetrahedron 24:13-32, 1968): Delta = 711.4, tau(m) = 47.3 (2), Delta C-2(C13-C14) = 5.7 (3), Delta C-s(C13) = 14.0 (3) and Delta C-s(C14) = 21.6 (3)degrees. The angle 77.20 (8)degrees between planes of the steroid-ABCD framework and phenyl ring evidences the relative orthogonal positions of these fragments. The H-1 and C-13 NMR characterization of the obtained compound are described.

• 出版日期2014-10