Conformations of derivatives of 3,7-diazabicyclo[3.3.1]nonan-9-one. Comparison of 3-ethoxycarbonyl-7-methyl-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one and 3,7-di(ethoxycarbonyl)-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one: effect of a nucleophile ? electrophile interaction on molecular geometry

McCabe, P. H.; Milne, N. J.; Sim, G. A.

doi:10.1039/p29890000831

Cited by 8 publications

(2 citation statements)

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“…More-pronounced spectral changes arise for the N -carboxylates 10 and 11 . First, due to partial multiple bond character and hindered rotation of the carbamate N–C bond, the symmetry of the compounds is reduced to C 1 for 10 and C 2 for 11 . Hence, for 10 , all eight NCH e H a protons and four NC atoms of the piperidine rings are inequivalent, as are the bridgehead H2a,b and C2a,b.…”

Section: Resultsmentioning

confidence: 99%

Bispidin-9,9-diol Analogues of Cisplatin, Carboplatin, and Oxaliplatin: Synthesis, Structures, and Cytotoxicity

et al. 2016

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3,7-Diallyl-bispidin-9-one (6) (bispidin-9-one = 3,7-diazabicyclo[3.3.1]nonan-9-one) is converted to N-unsubstituted spiro[bispidin-9,2'-[1,3]dioxolane] (12; 35%). The ketal crystallizes in the forms of anhydrous 12a and the dihydrate 12b. The molecules in anhydrous 12a are linked to each other, forming N1-H1···N2-H2···N1* hydrogen-bond chiral helices of alternating chirality. In the dihydrate 12b, the ketal molecules are connected to a central string of water molecules by O3-H···O1 and O4-H···N1 hydrogen bonds, but not to themselves. Reaction of 12 with (1,5-hexadiene)PtCl2 affords almost quantitatively spiro[bispidin-9,2'-[1,3]dioxolane]PtCl2 (13). Cleavage of the ketal to retrieve the ketone produces the geminal diol (bispidin-9,9-diol)PtCl2 (14; 85%). Compound 14 reacts with Ag2cbdca (cbdca = 1,1-cyclobutanedicarboxylate) to give the dihydrate (bispidin-9,9-diol)Pt(cbdca)·2H2O (15b), which can be dehydrated to obtain anhydrous (bispidin-9,9-diol)Pt(cbdca) (15a). Similarly, anhydrous (bispidin-9,9-diol)Pt(oxalate) (16) is obtained. Crystal structures of 14 and 15b reveal association by various forms of O-H···O, O-H···Cl, N-H···Cl, and N-H···O hydrogen bonds. Biological studies showed a moderate cytotoxic activity of the bispidin-9,9-diol complexes 14-16, compared to the 9,9-unsubstituted bispidine complexes. No unspecific cytotoxicity of 14-16 up to 316 μM was found against the noncancer cell line HEK293.

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Section: Resultsmentioning

confidence: 99%

Bispidin-9,9-diol Analogues of Cisplatin, Carboplatin, and Oxaliplatin: Synthesis, Structures, and Cytotoxicity

et al. 2016

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“…Also, this introduces a rather more dominating repulsive factor, the allylic A ( 1 , 3 ) strain, between the nitroso groups and the neighboring α-aryl groups in the BC conformation, making the CC conformer the chief one. 33–38 The conformational behavior of 3-borabicyclo[3.3.1]nonane 36 is rather more fascinating. The pπ–pπ backbonding between the filled p-orbital of oxygen and the vacant p-orbital of boron raises the bond order and restricts rotation around the B–O bond.…”

Section: Conformational Featuresmentioning

confidence: 99%