ChemInform Abstract: Planar Chiral Systems. Part 1. Optical Resolution of (2.2)Paracyclophanes by High‐Performance Liquid Chromatography on Tris‐2,5‐dimethylphenylcarbamates of Cellulose and Amylose.

Hopf, Henning; Grahn, Walter; Barrett, David; Gerdes, Anton; Hilmer, Jens-Michael; Hucker, Joachim; Kaida, Yuriko

doi:10.1002/chin.199028052

Cited by 2 publications

(2 citation statements)

References 2 publications

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“…The separation of a series of [2,2]paracyclophanes has been reported on Chiralcel OD and Chiralpak AD. 13 Inspection of the data for methyl, chloro, and fluoro substituted [2,2]paracyclophanes shows that retention on Chiralcel OD is almost insensitive to substitution whereas tremendous changes are observed between fluorine and chlorine on Chiralpak AD, in sharp contrast to what is observed on our rigid structure. These nonpolar compounds are nevertheless poorly separated compared to cyclophanes bearing more polar substituents.…”

Section: Solvation Of Carbamate Phasesmentioning

confidence: 81%

Chiral separation of some 4a‐methyl‐1,2,3,4,4a,9a‐hexahydro‐fluoren‐9‐one derivatives as a probe for difference in solvation by 2‐propanol of carbamate moiety in chiralcel OD‐H, chiralpak AD, and chiralpak AS chiral stationary phases

et al. 1998

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Chromatographic resolution of 12 derivatives in the 4a-methyl-2,3,4,4atetrahydro-1H-fluorene and 4a-methyl-1,2,3,4,4a,9a-hexahydrofluoren-9-one series differing by the framework around position 9 and substitution in position 6, are reported on Chiralcel OD, Chiralpak AD, and Chiralpak AS under two elution conditions and according to the two classes of enantiomers. Results from principal component analysis (PCA) as well as hierarchical clustering show a clustering of the actual compounds depending on properties around position 9, the effect of the substituent in position 6 (methyl, chloro or fluoro) not being strong enough to intermesh the data. Carbamate phases show very different properties when they are used in the separation of a series of ketones C and ␣-chloroketones D, which differ in basicity and the steric requirement around the carbonyl. Analysis of the effect of 2-PrOH content in hexane on the retention is consistent with a large difference in solvation of the carbamate moiety by 2-PrOH, in the order Chiralcel OD > Chiralpak AD > Chiralpak AS. 4a-Methyl-2,3,4,4a-tetrahydro-1H-fluorene derivatives, which lack hydrogen bonding sites, are not discriminated on these CSPs and show identical kЈ responses to 2-PrOH content changes on the three CSPs.

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Section: Solvation Of Carbamate Phasesmentioning

confidence: 81%

Chiral separation of some 4a‐methyl‐1,2,3,4,4a,9a‐hexahydro‐fluoren‐9‐one derivatives as a probe for difference in solvation by 2‐propanol of carbamate moiety in chiralcel OD‐H, chiralpak AD, and chiralpak AS chiral stationary phases

et al. 1998

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“…Adsorption on this material is occurred by interaction of the polar groups of the solute with the carbamate groups of the CSP via hydrogen bonding or dipole-dipole interaction [18]. Chiral recognition is probably brought about by the structure of higher order of the derivatized amylose, a left-handed helix with a chiral groove along the main chain [19].…”

Section: Discussionmentioning

confidence: 99%

Synthesis, Enantioseparation and Pharmacological Activity of 4-Aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones

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Ertan

et al. 2011

Arzneimittelforschung

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4-Aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione derivatives (1-8) have been prepared by modified Biginelli reaction from 5,5-dimethyl-1,3-cyclohexanedione, the aromatic aldehydes and thiourea. The structures of the compounds were confirmed by spectroscopic and elemental analysis. Racemic compounds were resolved into their enantiomers by HPLC using an amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase in the normal phase mode. The calcium antagonist activities of the compounds were determined by the tests performed on isolated rat ileum and lamb carotid artery. Compounds 2, 3, 4 and 6 were the most active compounds on isolated rat ileum. Compounds 2 and 3 were significantly active on lamb carotid artery.

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ChemInform Abstract: Planar Chiral Systems. Part 1. Optical Resolution of (2.2)Paracyclophanes by High‐Performance Liquid Chromatography on Tris‐2,5‐dimethylphenylcarbamates of Cellulose and Amylose.

Abstract: ChemInform Abstract Optical resolution of 22 (2.2)paracyclophanes such as (I) and (II) is examined by HPLC using tris-3,5-dimethylphenylcarbamates of cellulose and amylose as chiral stationary phases. Some of the cyclophanes are new, and their syntheses are described.

Cited by 2 publications

References 2 publications

Chiral separation of some 4a‐methyl‐1,2,3,4,4a,9a‐hexahydro‐fluoren‐9‐one derivatives as a probe for difference in solvation by 2‐propanol of carbamate moiety in chiralcel OD‐H, chiralpak AD, and chiralpak AS chiral stationary phases

Chiral separation of some 4a‐methyl‐1,2,3,4,4a,9a‐hexahydro‐fluoren‐9‐one derivatives as a probe for difference in solvation by 2‐propanol of carbamate moiety in chiralcel OD‐H, chiralpak AD, and chiralpak AS chiral stationary phases

Synthesis, Enantioseparation and Pharmacological Activity of 4-Aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones

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