Synthesis, crystal structures and biological activity of two enantiomeric 2-trifluoromethylthieno[2,3-d]pyrimidin-4-amine derivatives was written by Gao, Hui;Fu, Ju;Zhao, Ming-juan;Song, Xin-jian;Yang, Ping;Zheng, Yin. And the article was included in Chinese Journal of Structural Chemistry in 2015.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:
Two enantiomeric 2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine derivatives were synthesized by nucleophilic substitution of two chiral amines with 4-chloro-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine, which started from 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile, trifluoroacetic acid (TFA) and phosphoryl trichloride via one-pot procedure [I → II; II + (R)/(S)-α-methylbenzylamine → (R)/(S)-III]. Their structures were determined by single-crystal X-ray diffraction. Enantiomer (R)-III, (R)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system, space group P43 with a = 8.6847(6), b = 8.6847(6), c = 22.419(2) Å, V = 1690.9(3) Å3, Z = 4, Dc = 1.428 g/cm3, μ = 0.228 mm-1, F(000) = 752, the final R = 0.0463 and wR = 0.1257 for 3442 observed reflections with I > 2(I). Enantiomer (S)-III, (S)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system, space group P41 with a = 8.688, b = 8.688, c = 22.421 Å, V = 1692.4 Å3, Z = 4, Dc = 1.426 g/cm3, μ = 0.227 mm-1, F(000) = 752, the final R = 0.0682 and wR = 0.1806 for 3182 observed reflections with I > 2(I). The preliminary bioassay indicated that the R-enantiomer exhibits higher antitumor activity against MCF-7 than gefitinib. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).
2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts