4457-72-1Relevant articles and documents
PHEROMONES OF INSECTS AND THEIR ANALOGS. XXIX. METHYL-BRANCHED PHEROMONES FROM 4-METHYLTETRAHYDROPYRAN. 4. SYNTHESIS OF (+/-)-15,19,23-TRIMETHYLHEPTATRIACONTANE - A PHEROMONE OF Glossina morsitans morsitans
Odinokov, V. N.,Ishmuratov, G. Yu.,Kharisov, R. Ya.,Yakovleva, M. P.,Tolstikov, G. A.
, p. 361 - 363 (1991)
Racemic 15,19,23-trimethylheptatriacontane (the sex pheromone of the tsetse fly Glossina morsitans morsitans) has been synthesized from 1,5-dibromo-3-methylpentane, a product of the acid hydrolysis of 4-methyltetrahydropyran.
Process intensification-assisted conversion of α,ω-alkanediols to dibromides
Mekala, Shekar,Hahn, Roger C.
supporting information, p. 630 - 632 (2015/03/03)
The increasingly widespread applications of α,ω-dibromides motivated development of a scalable, inexpensive process to rapidly convert selected α,ω-alkanediols to the corresponding dibromides. Diols were heated with only 48% aq HBr and an organic solvent, using a Dean-Stark apparatus modified to fractionate the azeotropic distillate, thereby maintaining a higher HBr concentration and reaction rate in the pot. Intensified distillation also increased the reaction rate. Various other substrate, solvent, and parameter effects have been discovered and rationalized.
Light-mediated deoxygenation of alcohols with a dimeric gold catalyst
McCallum, Terry,Slavko, Ekaterina,Morin, Mathieu,Barriault, Louis
supporting information, p. 81 - 85 (2015/02/18)
A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.
Double-headed sulfur-linked amino acids as first inhibitors for betaine-homocysteine S -methyltransferase 2
Mládková, Jana,Vaněk, Václav,Budě?ínsky, Milo?,Elbert, Tomá?,Demianová, Zuzana,Garrow, Timothy A.,Jirá?ek, Ji?í
experimental part, p. 6822 - 6831 (2012/10/07)
Betaine-homocysteine S-methyltransferase 2 (BHMT-2) catalyzes the transfer of a methyl group from S-methylmethionine to l-homocysteine, yielding two molecules of l-methionine. It is one of three homocysteine methyltransferases in mammals, but its overall contribution to homocysteine remethylation and sulfur amino acid homeostasis is not known. Moreover, recombinant BHMT-2 is highly unstable, which has slowed research on its structural and catalytic properties. In this study, we have prepared the first series of BHMT-2 inhibitors to be described, and we have tested them with human recombinant BHMT-2 that has been stabilized by copurification with human recombinant BHMT. Among the compounds synthesized, (2S,8RS,11RS)-5-thia-2,11-diamino-8-methyldodecanedioic acid (11) was the most potent (Kiapp ~77 nM) and selective inhibitor of BHMT-2. Compound 11 only weakly inhibited human BHMT (IC 50 about 77 μM). This compound (11) may be useful in future in vivo studies to probe the physiological significance of BHMT-2 in sulfur amino acid metabolism.
Synthesis and biological characterization of (Z)-9-heptadecenoic and (Z)-6-methyl-9-heptadecenoic acids: Fatty acids with antibiotic activity produced by Pseudozyma flocculosa
Avis,Boulanger,Belanger
, p. 987 - 1000 (2007/10/03)
Difficulties in isolating and purifying antibiotic fatty acids from culture filtrates of Pseudozyma flocculosa, a biocontrol agent against powdery mildew, have been limiting factors in studying the properties and understanding the mode of action of the biocontrol agent. We report a new protocol for synthesizing (Z)-9-heptadecenoic and for the first time synthesis of (Z)-6-methyl-9-heptadecenoic acids, two antibiotic fatty acids produced by P. flocculosa. This allowed reproducible and quantifiable means of assaying biological activity of the molecules. In these bioassays, both molecules exhibited antifungal activity corresponding to their expected potency. These new developments should facilitate further studies aimed at deciphering the ecological properties of P. flocculosa.
A Convenient Synthetic Route to Methylated Silacyclohexanes
Nguyen, Binh T.,Cartledge, Frank K.
, p. 2206 - 2210 (2007/10/02)
The von Braun degradation of substituted piperidines is a general and economical route to a variety of substituted primary and secondary α,ω-dibromopentanes.Grignard ring closure procedures have been carried out with seven different dibromopentanes in moderate to good yields.Ring closures with MeClSiCl2 lead to product mixtures which are appreciably enriched in one isomer, affording a convenient entry into a variety of derivatives which can be used for stereochemical studies.Assignment of structures based on 1H NMR and mass spectral fragmentation patterns is discussed