25152-83-4Relevant academic research and scientific papers
HIGHLY STEREOCONTOROLLED SYNTHESIS OF (2E,4Z)-DIENIC ESTERS BY ALUMINA CATALYST
Tsuboi, Sadao,Masuda, Toshihide,Makino, Hiroshi,Takeda, Akira
, p. 209 - 212 (1982)
Thermal treatment of β-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,4Z)-dienoic esters (3) in 57-87percent yields with 91-100percent stereoselectivity.
Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms
Adolph, Sven,Poulet, Serge A.,Pohnert, Georg
, p. 3003 - 3008 (2003)
α,β,γ,δ-Unsaturated aldehydes have gained increasing attention since 2,4-decadienal and 2,4,7-decatrienal were isolated from the diatom Thalassiosira rotula and characterized as cell antiproliferative metabolites. Structurally related α,β,γ,δ-unsaturated aldehydes were found in this alga as well as in other diatom species. We present a short and universal synthesis of this compound class along with a structure-activity study of the potential to inhibit sea urchin egg cleavage. Pd0- or CoII-mediated cross coupling of 5-iodo-penta-2,4-dienal with organo-zincates allows the fast and flexible synthesis of numerous aldehydes from this universal precursor. The stereochemistry of the double bond system of the precursor was preserved during the coupling. Bioassays showed that the polarity of the side chain is important for antiproliferative activity with 2,4-decadienal as the most active compound tested compared to the shorter-chain aliphatic homologues and to ω-oxo acids with conjugated double systems. In contrast, the double bond geometry has no influence on biological activity. The α,β-unsaturated 2E-decenal was also highly active, while activity diminished in the case of saturated aldehydes of similar chain length. 1-Decanol, 2-decanone and decanoic acid were not active.
2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata
Akakabe, Yoshihiko,Matsui, Kenji,Kajiwara, Tadahiko
, p. 3607 - 3609 (2003)
Marine green alga Ulva conglobata was investigated for the biogeneration of oxygenated products from exogenously added arachidonic acid (ARA). A crude enzyme from the alga afforded the detectable amount of a hydroperoxyicosatetraenoic acid (HPITE), which was identified as (R)-11-HPITE by HPLC and GC-MS. Headspace-SPME method indicated that ARA was selectively used to form 2,4-decadienals. These results showed that 2,4-decadienals are produced via (R)-11-HPITE from ARA exclusively.
Model studies on the pattern of volatiles generated in mixtures of amino acids, lipid-oxidation-derived aldehydes, and glucose
Adams, An,Kitryte, Vaida,Venskutonis, Rimantas,De Kimpe, Norbert
experimental part, p. 1449 - 1456 (2011/10/05)
The development of flavor and browning in thermally treated foods results mainly from the Maillard reaction and lipid degradation but also from the interactions between both reaction pathways. To study these interactions, we analyzed the volatile compounds resulting from model reactions of lysine or glycine with aldehydes originating from lipid oxidation [hexanal, (E)-2-hexenal, or (2E,4E)-decadienal] in the presence and absence of glucose. The main reaction products identified in these model mixtures were carbonyl compounds, resulting essentially from amino-acid-catalyzed aldol condensation reactions. Several 2-alkylfurans were detected as well. Only a few azaheterocyclic compounds were identified, in particular 5-butyl-2-propylpyridine from (E)-2-hexenal model systems and 2-pentylpyridine from (2E,4E)-decadienal model reactions. Although few reaction products were found resulting from the condensation of an amino acid with a lipid-derived aldehyde, the amino acid plays an important role in catalyzing the degradation and further reaction of these carbonyl compounds. These results suggest that amino-acid-induced degradations and further reactions of lipid oxidation products may be of considerable importance in thermally processed foods.
Palladium catalyzed cross-coupling reaction of functional organozinc reagents with (2E,4E)- and (2E,4Z)-5-bromopenta-2,4-dienals: Easy access to functional conjugated dienic aldehydes
Vicart, Nicolas,Saboukoulou, Gerard-Simplice,Ramondenc, Yvan,Ple, Gerard
, p. 1509 - 1521 (2007/10/03)
Functional zinc reagents can be applied to palladium catalyzed cross-coupling reaction with (2E,4E)- and (2E,4Z)-5-bromopenta-2,4-dienal. The corresponding functional dienic aldehydes were obtained in goods yields. From the (2E,4E) isomer, the (2E,4E) dienals were isolated as single isomer according to a total stereoselective reaction. But, from the (2E,4Z) isomer the coupling reaction has lead to a mixture of (2E,4E) and (2E,4Z) isomers. A mechanism for the loss of stereoselectivity in the last case is proposed.
(2E)-4,4-dimethoxy-2-butenal in the synthesis of conjugated dienes and dienals
Badanyan,Makaryan,Ovanesyan,Panosyan
, p. 633 - 639 (2007/10/03)
Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)-and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds
Stereoselective synthesis of methyl and ethyl (2E,4Z)-2,4-decadienoates from (E)-4,4-dimethoxy-2-butenal
Ovanesyan,Garibyan,Badanyan
, p. 951 - 954 (2007/10/03)
Methyl and ethyl (2E,4Z)-2,4-decadienoates were synthesized starting from (E)-4,4-dimethoxy-2-butenal.
Regio- and Enantioselective Catalytic Epoxidation of Conjugated Polyenes. Formal Synthesis of LTA4 Methyl Ester
Chang, Sukbok,Lee, Nam Ho,Jacobsen, Eric N.
, p. 6939 - 6941 (2007/10/02)
The (salen)Mn(III)-catalyzed asymmetric epoxidation reaction exhibits regioselectivity for attack at cis double bonds of conjugated dienes to afford enantiomerically enriched trans-vinyl epoxides as the major products.
Oxidation of Alcohols with Electrolytic Manganese Dioxide. Its Application for the Synthesis of Insect Pheromones
Tsuboi, Sadao,Ishii, Naomi,Sakai, Takashi,Tari, Isao,Utaka, Masanori
, p. 1888 - 1893 (2007/10/02)
Oxidation of alcohols with electrolytic manganese dioxide under mild conditions afforded aldehydes and ketones in good yields.The method was applied for the syntheses of cystophorene (15) and a sex pheromone of forest tent cater pillar .
PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES
Andreini, Bianca Patrizia,Carpita, Adriano,Rossi, Renzo,Scamuzzi, Barbara
, p. 5621 - 5640 (2007/10/02)
On the basis of our observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prepare nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes (4), (E)-1-trimethylsilyl-1-alken-3-ynes (5), (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (6), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (8) from stereoisomeric mixtures of alkenyl bromides.Compounds 5 have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (7) by selective hydrometallations, followed by hydrolysis.Some synthetic applications of compounds 5-8 have been also examined.
