20125-85-3Relevant articles and documents
Natural trienoic acids as anticancer agents: First stereoselective synthesis, cell cycle analysis, induction of apoptosis, cell signaling and mitochondrial targeting studies
D’yakonov, Vladimir A.,Makarov, Alexey A.,Dzhemileva, Lilya U.,Ramazanov, Ilfir R.,Makarova, Elina Kh.,Dzhemilev, Usein M.
, (2021/04/13)
The first Z-stereoselective method was developed for the synthesis of unsaturated acids containing a 1Z,5Z,9Z-triene moiety in 61–64% yields using the new Ti-catalyzed cross-coupling of oxygen-containing and aliphatic 1,2-dienes as the key synthetic step. It was shown for the first time that trienoic acids with non-methylene-interrupted Z-double bonds show moderate cytotoxic activities against tumor cell lines (Jurkat, K562, U937, HL60, HeLa), human embryonic kidney cells (Hek293), normal fibroblasts and human topoisomerase I (hTop1) inhibitory activity in vitro. The synthesized acids efficiently initiate apoptosis of Jurkat tumor cells, with the cell death mechanism being activated by the mitochondrial pathway. A probable mechanism of topoisomerase I inhibition was also hypothesized on the basis of in silico studies resorting to docking. The activation and inhibition of the most versatile intracellular signaling pathways (CREB, JNK, NFkB, p38, ERK1/2, Akt, p70S6K, STAT3 and STAT5 tyrosine kinases) responsible for cell proliferation and for initiation of apoptosis were studied by multiplex assay technology (Luminex xMAP).
A simple and efficientin situgenerated copper nanocatalyst for stereoselective semihydrogenation of alkynes
Park, Byoung Yong,Lim, Taeho,Han, Min Su
supporting information, p. 6891 - 6894 (2021/07/19)
Development of a simple, effective, and practical method for (Z)-selective semihydrogenation of alkynes has been considered necessary for easy-to-access applications at organic laboratory scales. Herein, (Z)-selective semihydrogenation of alkynes was achieved using a copper nanocatalyst which was generatedin situsimply by adding ammonia borane to an ethanol solution of copper sulfate. Different types of alkynes including aryl-aryl, aryl-alkyl, and aliphatic alkynes were selectively reduced to (Z)-alkenes affording up to 99% isolated yield. The semihydrogenation of terminal alkynes to alkenes and gram-scale applications were also reported. In addition to eliminating catalyst preparation, the proposed approach is simple and practical and serves as a suitable alternative method to the conventional Lindlar catalyst.
NbCl5-Mg reagent system in regio-and stereoselective synthesis of (2Z)-alkenylamines and (3Z)-alkenylols from substituted 2-alkynylamines and 3-alkynylols
Dzhemilev, Usein M.,Gabdullin, Azat M.,Kadikova, Rita N.,Mozgovoj, Oleg S.,Ramazanov, Ilfir R.
supporting information, (2021/07/02)
The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5 –Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio-and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems—NbCl5-Mg and TaCl5-Mg, in relation to oxygen-and nitrogen-containing alkynes. A regio-and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene.
Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis
Bai, Zibo,Zhang, Heng,Wang, Hao,Yu, Hanrui,Chen, Gong,He, Gang
supporting information, p. 1195 - 1202 (2021/02/05)
An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to CuII-coordinated alkene is the enantio-determining step.
Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals
Kumari, Anupama,Gholap, Sachin P.,Fernandes, Rodney A.
, p. 2278 - 2290 (2019/06/17)
A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.
Selective Semihydrogenation of Alkynes with N-Graphitic-Modified Cobalt Nanoparticles Supported on Silica
Chen, Feng,Kreyenschulte, Carsten,Radnik, J?rg,Lund, Henrik,Surkus, Annette-Enrica,Junge, Kathrin,Beller, Matthias
, p. 1526 - 1532 (2017/08/15)
For the first time N-graphitic-modified cobalt nanoparticles (Co/phen@SiO2-800) are shown to be active in the semihydrogenation of alkynes to alkenes. Key to success for efficient catalysis is both the modification of the metal nanoparticles by nitrogen-doped graphitic layers and the use of silica as support. Several internal alkynes are converted to the Z isomer in high yields with up to 93% selectivity. In addition, a variety of terminal alkynes, including sensitive functionalized compounds, are readily converted into terminal alkenes. Notably, this non-noble-metal catalyst allows for the purification of alkenes by selective hydrogenation of the corresponding alkyne in the presence of an excess of olefin.
Novel Alkenyl Sulfate Ester or Salt Thereof
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Paragraph 0119, (2016/08/17)
Provided are a novel compound useful for adjusting sweetness or saltiness or inhibiting ENaC, and use thereof. An octenyl sulfate ester of the following Formula (1) or a salt thereof, wherein the wavy line represents any one of cis- or trans-configuration.
Palladium porphyrin catalyzed hydrogenation of alkynes: Stereoselective synthesis of cis -alkenes
Nishibayashi, Ryo,Kurahashi, Takuya,Matsubara, Seijiro
supporting information, p. 1287 - 1290 (2014/06/10)
(Tetraphenylporphyrin)palladium was developed as a catalyst for the chemoselective and stereoselective hydrogenation of alkynes to cis-alkenes by the syn-addition of hydrogen. Alkynes containing various functional groups were tolerated in the reaction, which gave the corresponding cis-alkenes in good to excellent yields. Georg Thieme Verlag Stuttgart New York.
Influence of the chemical structure on odor qualities and odor thresholds in homologous series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols
Lorber, Katja,Schieberle, Peter,Buettner, Andrea
, p. 1025 - 1031 (2014/03/21)
Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.
Influence of the chemical structure on odor qualities and odor thresholds in homologous series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols
Lorber, Katja,Schieberle, Peter,Buettner, Andrea
, p. 1025 - 1031 (2015/04/22)
Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.
