16493-96-2Relevant academic research and scientific papers
Palladium catalysed regio and stereoselective reduction of Baylis- Hillman coupling products derived allylic acetates
Pachamuthu, Kandaswamy,Vankar, Yashwant D.
, p. 5439 - 5442 (1998)
Acetates derived from a variety of the Baylis-Hillman products undergo reduction with HCOOH in the presence of Et3N, Pd(OAc)2, and dppe (or tri- isopropylphosphite) to yield the corresponding trisubstituted Z-olefins in good yields d
Metabolites of the Anaerobic Degradation of n-Hexane by Denitrifying Betaproteobacterium Strain HxN1
Küppers, Julian,Mitschke, Nico,Heyen, Simone,Rabus, Ralf,Wilkes, Heinz,Christoffers, Jens
, p. 373 - 380 (2019/11/19)
The constitutions of seven metabolites formed during anaerobic degradation of n-hexane by the denitrifying betaproteobacterium strain HxN1 were elucidated by comparison of their GC and MS data with those of synthetic reference standards. The synthesis of 4-methyloctanoic acid derivatives was accomplished by the conversion of 2-methylhexanoyl chloride with Meldrum's acid. The β-oxoester was reduced with NaBH4, the hydroxy group was eliminated, and the double bond was displaced to yield the methyl esters of 4-methyl-3-oxooctanoate, 3-hydroxy-4-methyloctanoate, (E)-4-methyl-2-octenoate, and (E)- and (Z)-4-methyl-3-octenoate. The methyl esters of 2-methyl-3-oxohexanoate and 3-hydroxy-2-methylhexanoate were similarly prepared from butanoyl chloride and Meldrum's acid. However, methyl (E)-2-methyl-2-hexenoate was prepared by Horner–Wadsworth–Emmons reaction, followed by isomerization to methyl (E)-2-methyl-3-hexenoate. This investigation, with the exception of 4-methyl-3-oxooctanoate, which was not detectable in the cultures, completes the unambiguous identification of all intermediates of the anaerobic biodegradation of n-hexane to 2-methyl-3-oxohexanoyl coenzyme A (CoA), which is then thiolytically cleaved to butanoyl-CoA and propionyl-CoA; these two metabolites are further transformed according to established pathways.
Simple access to 2-methylalk-2-enoates and insect pheromones by zinc-promoted reduction of Baylis-Hillman-derived allylic bromides
Fernandes, Luciano,Bortoluzzi, Adailton J.,Sá, Marcus M.
, p. 9983 - 9989 (2007/10/03)
(E)-2-Methylacrylates are prepared in good yield and high stereoselectivity by zinc-promoted reduction of 2-(bromomethyl)alkenoates derived from Baylis-Hillman adducts. Synthesis of the male ant pheromone (E)-2,4-dimethyl-2- hexenoic acid was performed using this simple methodology. (E)-2-Methylacrylates are easily prepared by zinc-promoted reduction of 2-(bromomethyl)alkenoates derived from Baylis-Hillman adducts. Synthesis of the male ant pheromone (E)-2,4-dimethyl-2-hexenoic acid was performed using this simple methodology.
A facile one-pot synthesis of methyl(2E)-2-methylalk-2-enoates from Baylis-Hillman adducts under microwave irradiation
Ravichandran
, p. 2055 - 2057 (2007/10/03)
A facile procedure for the synthesis of the title compound is described.
DABCO-Catalyzed Coupling of Aldehydes with Activated Double Bonds. 4. Stereoselective Synthesis of Trisubstituted Olefins and Terpenoid Building Blocks via 2-(Hydroksyalkyl)-2-propenoic Esters.
Hoffmann, H. Martin R.,Rabe, Juergen
, p. 3849 - 3859 (2007/10/02)
A variety of 2-(hydroksyalkyl)-2-propenoic esters 16a-g has been prepared in high yield by DABCO-catalyzed coupling of aldehydes 14a-g with methyl acrylate.The product esters 16a-g are useful building blocks in syntheses which undergo regioselective and Z-selective SN2 reactions with N-bromosuccinimide/dimethyl sulfide and N-chlorosuccinimide/dimethyl sulfide to furnish (Z)-2-(bromomethyl)-2-alkenoic esters 17a-g and (Z)-2-(chloromethyl)-2-alkenoic esters 18b,c,d, respectively.Similarly, the derived allylic acetates 21g,h, and also allylic bromide 17g react with lithium triethylhydridoborate via mechanism SN2' to give (E)-2-methyl-2-alkenoic esters 22g,h and respectively, 2-methylenealkanoic esters 20g.Methyl (Z)-6,6-(ethylenedioxy)-2-methyl-2-heptenoate (22h) has been prepared as an intermediate en route to the norsesquiterpenoid ketone 23.The allylic bromides 17d,e,f also furnish (Z)-6-methyl-5--4-heptene-1,6-diol (19a), (Z)-2-methyl-3--3-octene-2,7-diol (19e), and (Z)-7-methyl-6--5-octene-1,2,7-triol (19f), which are terpenoid building blocks.
