INDUCED ASYMMETRY AND OPTICAL RESOLUTION OF 2-PHENYLPYRIDINE DERIVATIVES

1938 ◽  
Vol 16b (4) ◽  
pp. 109-113 ◽  
Author(s):  
J. G. Breckenridge ◽  
O. C. Smith
Keyword(s):  
Dicarboxylic Acid ◽  
Acid Derivative ◽  
Opposite Direction ◽  
Optical Rotation ◽  
Dimethyl Ester ◽  
Optical Resolution ◽  
Cinchona Alkaloids ◽  
Diphenic Acid

It was shown in 1927 that quinine, when combined with a diphenic acid derivative, gave a salt with an optical rotation in the opposite direction to that of the free alkaloid ("Kuhn's effect"). The present authors have prepared the salts of four of the cinchona alkaloids with 2-phenylpyridine-2′:3-dicarboxylic acid, and find similar results. In addition, a partial optical resolution of a derivative of this acid has been effected, the dextro-form of the methiodide of the dimethyl ester having been isolated.

Optical resolution of 1-(1-naphthyl)ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair

Chirality ◽  
2009 ◽  
Vol 21 (3) ◽  
pp. 331-338 ◽  
Author(s):  
Laura Bereczki ◽  
Petra Bombicz ◽  
József Bálint ◽  
Gabriella Egri ◽  
József Schindler ◽  
...  
Keyword(s):  
Oxalic Acid ◽  
Dicarboxylic Acid ◽  
Acid Derivative ◽  
Optical Resolution ◽  
Structural Features

Comparing the host behaviour of roof-shaped compounds trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid and its dimethyl ester in the presence of mixtures of xylene and ethylbenzene guests

CrystEngComm ◽  
2021 ◽  
Author(s):  
Benita Barton ◽  
Ulrich Senekal ◽  
Eric Cyriel Hosten
Keyword(s):  
Dicarboxylic Acid ◽  
Dimethyl Ester ◽  
Host Behaviour

Here we compare the host behaviour of two roof-shaped compounds, trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid H1 and its dimethyl ester, trans-dimethyl 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate H4, when presented with mixed xylene (o-Xy, m-Xy and p-Xy) and...

Natural Inhibitors of Germination and Growth, III New α-Pyrones from Seeds of Rosa canina

1985 ◽  
Vol 40 (7-8) ◽  
pp. 490-495 ◽  
Author(s):  
Edith Lohaus ◽  
Claudia Zenger ◽  
Wolfhart Rüdiger ◽  
Edmund Cmiel
Keyword(s):  
Nmr Spectroscopy ◽  
Dicarboxylic Acid ◽  
Parent Compound ◽  
Dimethyl Ester ◽  
Rosa Canina ◽  
Relationship Of ◽  
Germination And Growth ◽  
The Relationship ◽  
Natural Inhibitors ◽  
C Nmr

Abstract The new α-pyrone derivative II was isolated in crystalline form from extracts of dormant seeds of Rosa canina. It inhibits germination of seeds of Amaranthus caudatus completely, but reversibly, at conc. > 2.5 × 10-5 м . Its chemical structure was elucidated by mass spectrometry, 1H-and 13C-NMR spectroscopy to be 3-methyl-1-oxa-bicyclo (4,1,0) hept-5-en-2-one-4,6-dicarboxylic acid di­methylester (II). It is derived from 3-methyl-2H-pyran-2-one-4,6-dicarboxylic acid by cyclo-propanation with diazomethane. The parent compound which is a natural product of the seeds of Rosa canina was isolated as its dimethyl ester I the structure of which was elucidated by mass and NMR spectroscopy. I shows less inhibition of seed germination than II. The reference a-pyrones dimethyl-6-methyl-2H-pyran-2-one-3,5-dicarboxylate (III) , 3-methoxycarbonyl-5-methoxycar-bonylmethyl-6-methyl-2H-pyran-2-one (IV), and isodehydracetic acid methylester (V) did not show any inhibitory activity. The relationship of II with threo-dihydrohematinic acid (VII) is discussed.

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