64437-42-9Relevant academic research and scientific papers
Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): A synthetic approach to the chemical analysis of trace quantities of a natural product
Cravatt, Benjamin F.,Lerner, Richard A.,Boger, Dale L.
, p. 580 - 590 (2007/10/03)
The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Δ-sleep-inducing peptide and prostaglandin D2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of sleep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.
Synthesis of Natural Compounds with Alkyl-methoxy-1,4-benzoquinone Structure
Pfeifer, Jochen,Gerlach, Hans
, p. 131 - 138 (2007/10/02)
The 1,4-benzoquinones 1-7 occurring in various plants and having interesting biological properties have been synthesized from the tetrahydropyranyl ethers 17 and 21.Reaction with n-butyllithium gave selectively the ortho-lithiated compounds.These could be alkylated with the haloalkenes 13-16 and haloalkanes to give the substituted phenols 18-20 and 22-25 in high yield after methanolysis.Alkylations of the methoxyisopropylether 8 of 10-undecyn-1-ol with bromobutane and bromohexane gave 9 and 10.These alkynols could be selectively hydrogenated with Lindlar-Palladium catalyst to give the (Z)-alkenols 11 and 12 which could be converted into the bromoalkenes 13, 14 and the iodoalkenes 15, 16.Oxidation of the phenols 18-20 and 22-25 with molecular oxygen in the presence of salcomine as catalyst produced the substituted 1,4-benzoquinones 1-3 and 26-29 in high yield.Selective hydrolysis with perchloric acid converted 26-29 into the natural products 4-7. - Key Words: Tetrahydropyranyl-ethers / ortho-Lithiation / ortho-Alkylation / 1,4-Benzoquinones, alkyl-methoxy- / 1,4-Benzoquinones, alkyl-hydroxy-methoxy-
A CONVENIENT SYNTHESIS OF 2,13- AND 3,13-OCTADECADIENYL ACETATES, SEX PHEROMONE COMPONENTS OF THE Synanthedon SPECIES
Hoskovec, Michal,Saman, David,Koutek, Bohumir
, p. 2270 - 2281 (2007/10/02)
The sex pheromone components of several Synanthedon species, 2,13- and 3,13- octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation.Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30percent overall yields.Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene.The title pheromones were generated in more than 97percent stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.
Synthesis of (2E, 13Z)-2, 13-octadecadien-1-yl acetate
Sharma,Thapar,Gupta
, p. 657 - 658 (2007/10/02)
(2E, 13Z)-2, 13-Octadecadien-1-yl acetate (1), a new pheromone from the moths of Sesiidae family has been synthesized employing copper (I) and copper (II) catalyzed coupling reactions as the key steps.
A New Highly Stereospecific Synthesis of (E,Z)-2,13-octadecadienyl Acetate, a Sex Pheromone Component of Some Lepidoptera Species.
Ramiandrasoa, F.,Descoins, C.
, p. 2703 - 2712 (2007/10/02)
The synthesis of the Z moiety of the title compound has been achieved by carbocupration of acetylene followed by alkylation with the appropriate organozinc reagent in the presence of catalytic Pd0.The coupling of this intermediate with protecte
SYNTHESIS OF PHEROMONES, IV. CHEMISTRY OF THE WITTIG REACTION, I. EFFECTS OF REACTION CONDITIONS ON THE STEREOSELECTIVITY AND YIELD OF THE WITTIG REACTION
Vinczer, Peter,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba
, p. 797 - 820 (2007/10/02)
The reactions of nonstabilized triphenylphosphorus ylides with aldehydes have been studied in detail.The stereochemistry and yields of the alkene products are highly dependent upon base used for the generation of the ylide, the solvent and reaction temperature.The synthesis of sex pheromone components by Wittig reaction are also described.
ISOLATION, STRUCTURE AND SYNTHESIS OF MAESANIN, A HOST DEFENSE STIMULANT FROM AN AFRICAN MEDICINAL PLANT MAESA LANCEOLATE
Kubo, Isao,Kim, Mujo,Ganjian, Iraj,Kamikawa, Tadao,Yamagiwa, Yoshiro
, p. 2653 - 2660 (2007/10/02)
The isolation, characterization and an efficient synthesis of maesanin 1, a host defense stimulant isolated from an African medicinal plant Maesa lanceolate, is reported.
A NOVEL STEREOCONTROLLED SYNTHESIS OF (Z,Z)-3,13-OCTADECDIEN-1-YL ACETATE, THE SEX PHEROMONE OF SYNANTHEDON SPECIES
Vinczer, Peter,Baan, Gabor,Novak, Lajos,Szantay, Csaba
, p. 2701 - 2704 (2007/10/02)
Starting from 10-undecenoic acid, a stereocontrolled synthesis of (Z,Z)-3,13-octadecadien-1-yl acetate with high sterochemical purity was achieved by the use of Wittig-olefinations for the introductions of (Z)-double bonds.
ISOLATION, STRUCTURE AND SYNTHESIS OF MAESANIN, A HOST DEFENSE STIMULANT FROM AN AFRICAN MEDICINAL PLANT MAESA LANCEOLATA
Kubo, Isao,Kamikawa, Tadao,Miura, Iwao
, p. 3825 - 3828 (2007/10/02)
The isolation, characterization and an efficient synthesis of maesanin 1, a host defense stimulant isolated from an African medicinal plant Maesa lanceolata is reported.
