GEOMETRICAL OPTIMIZATIONS, NMR ANALYSES, AND NOVEL CRYSTAL STRUCTURES OF 3-OXA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE AND 3-THIA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE; STRUCTURAL ANALYSIS OF THE CORRESPONDING 3,7-DIHETERABICYCLO[3.3.l]NONANE HYDROPERCHLORATES

Berlin, K. Darrell; Tyagi, Sameer; Rahaman, Asif; Qiu, Feng; Raff, Lionel M.; Venkatramani, Lalitha; Khan, Massod A.; Helm, D. van der; Yu, V. К.; Пралиев, К. Д.

doi:10.1080/10426509908037003

Phosphorus, Sulfur, and Silicon and the Related Elements

1999

DOI: 10.1080/10426509908037003

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GEOMETRICAL OPTIMIZATIONS, NMR ANALYSES, AND NOVEL CRYSTAL STRUCTURES OF 3-OXA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE AND 3-THIA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE; STRUCTURAL ANALYSIS OF THE CORRESPONDING 3,7-DIHETERABICYCLO[3.3.l]NONANE HYDROPERCHLORATES

K. Darrell Berlin

Sameer Tyagi

Asif Rahaman

et al.

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Cited by 4 publications

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“…Hence, we should be careful in assuming that the structures established for the crystalline state and calculated for the gaseous state actually exist in real solutions. If the energy difference between the double chair and chair-boat conformers is slight (on the order of only 1.5 kcal/mol) [3], a change in the solvent, temperature, or concentration can shift the equilibrium toward another form. 1-14 X = S, 15-17 X = N(CH 2 ) 2 OEt; 1, 6 R = (CH 2 ) 2 OMe; 2, 7, 11 R = (CH 2 ) 2 OEt; 3, 8, 12 R = (CH 2 ) 3 OEt; 4, 9, 13 R = (CH 2 ) 3 OBu; 5, 10, 14 R = (CH 2 ) 3 OPr-i 1 H NMR spectroscopy permits us to determine which of the forms in solution is predominant.…”

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confidence: 99%

1H NMR spectroscopy in the study of the three-dimensional structure of 7-alkoxyalkyl-3-thia-7-azabicyclo-[3.3.1]nonan-9-ones and some of their derivatives

Клепикова¹,

Yu²,

Fomicheva³

et al. 2008

Chem Heterocycl Comp

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H NMR spectroscopy was used to establish that 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-onesand their decarbonylated derivatives in deuterochloroform solution exist in the double chair conformation. The predominantly formed secondary alcohols isomers have preferred double chair conformation with the hydroxyl group equatorial relative to the plane of the piperidine ring. On the other hand, the epimeric alcohols have predominant boat-chair conformation; the piperidine ring takes the boat form due to intramolecular hydrogen bonding between the unshared electron pair of the nitrogen atom and hydroxyl group proton.Keywords: 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]non-9-one and its derivatives, conformational analysis, 1 H NMR spectra.The study of the three-dimensional structure of bicyclic compounds containing important biogenic elements such as oxygen, nitrogen, and sulfur holds interest not only in regard to the search for new physiologically active compounds but also for the development of conformational analysis and stereochemistry. We have described the synthesis of a series of 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]non-9-ones, their deoxygenated derivatives, and derived secondary alcohols [1]. In the present work, we have determined the three-dimensional structure of these compounds using high resolution 1 H NMR spectroscopy. We studied ketones 1-5 with various substituents at the nitrogen atom, their reduced analogs 6-10, and secondary alcohols 11-14. The chemical shifts and coupling constants for the individual stereoisomers isolated from alcohols 11 and 12 were used to interpret the rather complex spectra of alcohols 13 and 14, each of which is a mixture of two isomers that could not be separated.Bicyclo[3.3.1]nonanes and their 3,7-dihetero analogs exist in solution as one of four forms: double chair (cc), chair-boat (cb), boat-chair (bc), and double boat (bb) or as a mixture in conformational equilibrium [2]. The predominant configuration is determined not only by the overall electronic and steric factors within these __________________________________________________________________________________________

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mentioning

confidence: 99%

1H NMR spectroscopy in the study of the three-dimensional structure of 7-alkoxyalkyl-3-thia-7-azabicyclo-[3.3.1]nonan-9-ones and some of their derivatives

Клепикова¹,

Yu²,

Fomicheva³

et al. 2008

Chem Heterocycl Comp

Self Cite

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Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using¹H NMR Spectroscopy

Клепикова

Fomicheva

et al. 2003

Chemistry of Heterocyclic Compounds

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Synthesis, Stereochemical, and Conformational Studies of Selected 3,7-Diheterabicyclo[3.3.1]nonan-9-ols: X-Ray Diffraction Analyses of 7-Benzyl-9-phenyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ol and 7-Benzyl-9-(4-N,N′-dimethylaminophenyl)-3-thia-7-azabicyclo[3.3.1]nonan-9-ol, a Rare Stable Chair–Boat Form With Trigonal Nitrogen

Tran

Berlin

Eastman

et al. 2007

Phosphorus, Sulfur, and Silicon and the Related Elements

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GEOMETRICAL OPTIMIZATIONS, NMR ANALYSES, AND NOVEL CRYSTAL STRUCTURES OF 3-OXA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE AND 3-THIA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE; STRUCTURAL ANALYSIS OF THE CORRESPONDING 3,7-DIHETERABICYCLO[3.3.l]NONANE HYDROPERCHLORATES

Cited by 4 publications

References 20 publications

1H NMR spectroscopy in the study of the three-dimensional structure of 7-alkoxyalkyl-3-thia-7-azabicyclo-[3.3.1]nonan-9-ones and some of their derivatives

1H NMR spectroscopy in the study of the three-dimensional structure of 7-alkoxyalkyl-3-thia-7-azabicyclo-[3.3.1]nonan-9-ones and some of their derivatives

Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using¹H NMR Spectroscopy

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GEOMETRICAL OPTIMIZATIONS, NMR ANALYSES, AND NOVEL CRYSTAL STRUCTURES OF 3-OXA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE AND 3-THIA-7-BENZYL-7-AZABICYCLO[3.3.1]-NONAN-9-ONE; STRUCTURAL ANALYSIS OF THE CORRESPONDING 3,7-DIHETERABICYCLO[3.3.l]NONANE HYDROPERCHLORATES

Cited by 4 publications

References 20 publications

1H NMR spectroscopy in the study of the three-dimensional structure of 7-alkoxyalkyl-3-thia-7-azabicyclo-[3.3.1]nonan-9-ones and some of their derivatives

1H NMR spectroscopy in the study of the three-dimensional structure of 7-alkoxyalkyl-3-thia-7-azabicyclo-[3.3.1]nonan-9-ones and some of their derivatives

Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using1H NMR Spectroscopy

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Study of the Steric Structure of 7-Alkoxyalkyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-ones and Their Derivatives Using¹H NMR Spectroscopy