Studies of stereochemical influences upon anti-histaminic activity. The synthesis, configuration, and anti-histaminic properties of some isomeric aminobutenes

1969 ◽  
Vol 47 (3) ◽  
pp. 423-427 ◽  
Author(s):  
A. F. Casy ◽  
A. P. Parulkar
Keyword(s):  
Double Bond ◽  
Magnetic Resonance ◽  
Spectroscopic Data ◽  
Proton Magnetic Resonance ◽  
Acid Catalyzed ◽  
Related Compounds

The acid-catalyzed dehydration of 4-dimethylamino-2-p-methoxyphenyl-1-phenylbutan-2-ol yields all four possible 4-amino-1,2-diarylbutenes. Pure samples of each isomer have been isolated, double bond positions and configurations being established from proton magnetic resonance and ultraviolet spectroscopic data. A stereoselective route to cis aminobut-1-enes has been further investigated. The anti-histaminic properties of the reported butenes together with some related compounds are given and structural influences upon activity discussed.

Dehydration of alcohols derived from 1-t-butyl-3-dimethylaminopropan-1-one; a novel cleavage reaction involving 2,6-dichlorobenzylmagnesium bromide

1970 ◽  
Vol 48 (6) ◽  
pp. 1011-1013 ◽  
Author(s):  
A. F. Casy ◽  
R. R. Ison
Keyword(s):  
Magnetic Resonance ◽  
Spectroscopic Data ◽  
Proton Magnetic Resonance ◽  
Tertiary Alcohol ◽  
Cleavage Reaction ◽  
Butyl Group ◽  
Acid Catalyzed ◽  
Cis And Trans

The acid-catalyzed dehydration of 1-t-butyl-3-dimethylamino-1-phenylpropan-1-ol gives cis(t-Bu/H)1-t-butyl-3-dimethylamino-1-phenylprop-1-ene exclusively. Dehydration of the product of reaction between 1-t-butyl-3-dimetnylammopropari-1-one and 2,6-dichlorobenzylmagnesium bromide gives cis and trans 2-t-butyl-1-2,6-dichlorophenyl-4-dimethylaminobut-2-ene plus the cis aminopropene of the first reaction. The formation of the aminopropene, together with that of its precursor tertiary alcohol, represents a novel cleavage reaction of 2,6-dichlorobenzylmagnesium bromide. The configurations of the aminoalkenes were established from proton magnetic resonance spectroscopic data, the cis(t-Bu/H)but-2-ene providing a further example of a magnetically non-equivalent t-butyl group.

Physicochemical properties of some new 1,5- and 5,5-alkyl-substituted barbituric acids

1970 ◽  
Vol 48 (14) ◽  
pp. 2274-2279 ◽  
Author(s):  
G. A. Neville ◽  
H. W. Avdovich ◽  
A. W. By
Keyword(s):  
Magnetic Resonance ◽  
Physicochemical Properties ◽  
Spectroscopic Data ◽  
Proton Magnetic Resonance ◽  
Hydroxy Derivative ◽  
The Novel

The synthesis of six new barbituric acids 1b, 3a, 4b, 5, and 6b, including the novel 5-hydroxy derivative 3b, is reported together with spectroscopic data (proton magnetic resonance, ultraviolet, and infrared) for these and for five related known barbiturates for which such data is lacking. An interesting occurrence of non-equivalence of the N-1 and N-3 CH2(Et) protons in 3b is discussed.

Conformational studies of some 5,9-dimethyl-6,7-benzomorphan diastereoisomers and related compounds

1969 ◽  
Vol 47 (19) ◽  
pp. 3623-3630 ◽  
Author(s):  
A. F. Casy ◽  
A. P. Parulkar
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Piperidine Ring ◽  
Free Base ◽  
Conformational Studies ◽  
Related Compounds

The proton magnetic resonance characteristics of some α/β diastereoisomeric 5,9-dimethyl-6,7-benzomorphans are reported for free base, hydrohalide, and methiodide forms, and differences between α- and β-signals are interpreted in terms of the piperidine ring fragment of the β-salts adopting skew-boat conformations. The steric course of quaternization of benzomorphan isomers is discussed from results of alkylations using trideuteriomethyl iodide and other experiments. A possible correlation between conformational and potency differences in analgesically active benzomorphan diastereoisomers and related compounds is discussed.

scholarly journals Structure Determination of Two New Monocillin I Derivatives

2010 ◽  
Vol 5 (5) ◽  
pp. 1934578X1000500
Author(s):  
Jixun Zhan ◽  
E. M. Kithsiri Wijeratne ◽  
A. A. Leslie Gunatilaka
Keyword(s):  
Double Bond ◽  
Acid Solution ◽  
Beauveria Bassiana ◽  
Structure Determination ◽  
Spectroscopic Data ◽  
Enzymatic Process ◽  
Acid Catalyzed ◽  
Hydrolysis Of

Biotransformation of monocillin I (1) by Beauveria bassiana ATCC 7159 was investigated. Two new derivatives 2 and 3 were isolated and identified on the basis of the spectroscopic data. Compounds 2 and 3 are synthesized by hydration at 10,11-double bond and hydrolysis of 14,15-epoxide, respectively. The R configuration of 11-OH in 2 was established by the modified 2-methoxy-2-trifluoromethylphenylacetic acid (MTPA) method. The conversion of 1 to 2 and 3 was reconstituted in an acid solution, indicating that the formation of 2 and 3 is an acid-catalyzed instead of an enzymatic process.

Carbamylphosphonates and Related Compounds—Nuclear-Magnetic-Resonance and Infrared Spectra

1967 ◽  
Vol 21 (1) ◽  
pp. 9-15 ◽  
Author(s):  
T. H. Siddall ◽  
C. A. Prohaska
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Infrared Spectra ◽  
Proton Magnetic Resonance ◽  
Structural Features ◽  
Slow Rotation ◽  
The Common ◽  
Related Compounds ◽  
Great Evidence ◽  
Nitrogen Bond

Proton magnetic resonance and infrared spectra were obtained for 44 carbamylphosphonates and related compounds, the common structural features being the grouping As with ordinary amides, slow rotation is observed around the carbonyl-to-nitrogen bond, but the chemical shift between nitrogen substituents is three to five times as great. Evidence is presented for long range coupling of phosphorus to protons in N-substituents. Correlations are observed between the carbonyl and phosphoryl stretching frequencies and substituents both on nitrogen and on phosphorus.

Proton magnetic resonance and mass spectrometric studies on derivatives of sodium 2-O-α-D-mannopyranosyl-D-glycerate and related compounds

1969 ◽  
Vol 47 (21) ◽  
pp. 4083-4086 ◽  
Author(s):  
J. N. C. Whyte
Keyword(s):  
Magnetic Resonance ◽  
Methyl Ester ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Red Alga ◽  
Mass Spectrometric ◽  
Derivatives Of ◽  
Related Compounds

The proton magnetic resonance (p.m.r.) and mass spectra of the methyl ester pentaacetate of sodium 2-O-α-D-mannopyranosyl-D-glycerate from the red alga Rhodomela larix are compared to those of related compounds to affirm the assigned structure.

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