Synthesis of trans-3,cis-5-tetradecadienoic acid (megatomoic acid), the sex attractant of the black carpet beetle, and its geometric isomers

1970 ◽  
Vol 35 (9) ◽  
pp. 3152-3154 ◽  
Author(s):  
J. Otto. Rodin ◽  
M. A. Leaffer ◽  
Robert M. Silverstein
Keyword(s):  
Sex Attractant ◽  
Geometric Isomers ◽  
Black Carpet Beetle ◽  
Megatomoic Acid

Isomerization of acetylenic acids with sodium salt of 1,2-diaminoethane: a one step synthesis of megatomoic acid

1982 ◽  
Vol 60 (10) ◽  
pp. 1238-1243 ◽  
Author(s):  
S. R. Abrams
Keyword(s):  
Sex Pheromone ◽  
Sodium Salt ◽  
Triple Bond ◽  
Carboxyl Group ◽  
One Step ◽  
Acetylenic Acids ◽  
Black Carpet Beetle ◽  
Megatomoic Acid

A number of isomeric tetradecynoic acids were isomerized with the sodium salt of 1,2-diaminoethane. Isomers having the triple bond near the carboxyl group rearranged to E,Z-3,5- and E,E-3,5-tetradecadienoic acids (1 and 2), the former compound being the sex pheromone of the black carpet beetle. Isomers having the triple bond closer to the terminus of the chain afforded some 13-tetradecynoic acid along with 1 and 2. Delocalized anions 12 and 13 are thought to contribute to the formation of 1 and 2.

Sex Attractant of the Black Carpet Beetle

Science ◽  
1967 ◽  
Vol 157 (3784) ◽  
pp. 85-87 ◽  
Author(s):  
R. M. Silverstein ◽  
J. O. Rodin ◽  
W. E. Burkholder ◽  
J. E. Gorman
Keyword(s):  
Sex Attractant ◽  
Black Carpet Beetle

Short-route synthesis of (3E,5Z)-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle

2001 ◽  
Vol 25 (2) ◽  
pp. 223-225 ◽  
Author(s):  
Jhillu S. Yadav ◽  
Etukala Jagan Reddy ◽  
Tallapali Ramalingam
Keyword(s):  
Sex Attractant ◽  
Short Route ◽  
Black Carpet Beetle

ChemInform Abstract: Short-Route Synthesis of (3E,5Z)-Tetradecadienoic Acid (Megatomic Acid), the Sex Attractant of the Black Carpet Beetle.

ChemInform ◽  
2010 ◽  
Vol 32 (24) ◽  
pp. no-no
Author(s):  
Jhillu S. Yadav ◽  
Etukala Jagan Reddy ◽  
Tallapali Ramalingam
Keyword(s):  
Sex Attractant ◽  
Short Route ◽  
Black Carpet Beetle

Synthesis of the semi-rigid analogues of prothiadene and dithiadene as potential antidepressant and antihistamine agents: 11-[2-(Dimethylaminomethyl)cyclohexylidene]-6,11-dihydrodibenzo[b,e]thiepins and 4-[2-(dimethylaminomethyl)cyclohexylidene]-4,9-dihydrothieno-[2,3-c]-2-benzothiepins

1985 ◽  
Vol 50 (5) ◽  
pp. 1078-1088 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jan Metyš ◽  
Miroslav Protiva
Keyword(s):  
Hydrochloric Acid ◽  
Ir Spectrum ◽  
Title Compound ◽  
Dilute Hydrochloric Acid ◽  
Amino Alcohols ◽  
Geometric Isomers ◽  
Pharmacological Testing

Reaction of dibenzo[b,e]thiepin-11(6H)-one with 2-(dimethylaminomethyl)cyclohexylmagnesium chloride gave a mixture of stereoisomeric amino alcohols IX from which four homogeneous bases (IXa to IXd) were separated by chromatography. Dehydration of these compounds with boiling dilute hydrochloric acid afforded mixtures of racemic geometric isomers of the title compound VII, which were separated by crystallization. To the prevailing less polar base VIIa (E)-configuration was assigned on the basis of the IR spectrum. Using a similar procedure, thieno[2,3-c]-2-benzothiepin-4(9H)-one gave mixture of amino alcohols X from which three homogeneous stereoisomers X-A to X-C were isolated. Their dehydration resulted in both expected racemic geometric isomers VIII-A and VIII-B. Pharmacological testing proved the character of an antidepressant for the semi-rigid analogue of dithiadene VIII.

15N, 13C, and 1H NMR Spectra of Azo and Hydrazo Compounds Derived from 1,3,3-Trimethyl-2-methylidene-2,3-dihydroindole (Fischer Base)

1998 ◽  
Vol 63 (7) ◽  
pp. 1012-1020 ◽  
Author(s):  
Antonín Lyčka ◽  
Josef Jirman ◽  
Alois Koloničný
Keyword(s):  
Double Bond ◽  
Hydrochloric Acid ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
Azo Compounds ◽  
Passive Component ◽  
Geometric Isomers ◽  
H Nmr ◽  
Fischer Base ◽  
Hydrazone Form

The 15N, 13C, and 1H NMR spectra were measured for azo and hydrazo compounds derived from 1,3,3-trimethyl-2-methylidene-2,3-dihydroindole (Fischer base), which is a passive component with a terminal methylidene group. Products prepared by coupling in hydrochloric acid exist in the corresponding hydrazone form as the E-isomers. Neutralization gives a mixture of two isomeric azo compounds which differ in the arrangement at the C(2)=C(10) double bond. This mixture was alkylated with methyl iodide to obtain the =N-N(CH3)- hydrazone derivatives. The geometric isomers were resolved based on the NOESY approach and the stereospecific behaviour of the 2J(15N,13C) coupling constants was studied for the 15N-labelled compounds.

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