5604-55-7

Usage

InChI:InChI=1/C5H8O/c1-2-3-4-5-6/h2-3,5H,4H2,1H3

Upstream product

• 6736-21-6 3-pentene-1,2-diol 
• 201230-82-2 carbon monoxide 
• 106-99-0 buta-1,3-diene 
• 62946-61-6 trans-1,2-dihydroxy-3-pentene 
• 25073-25-0 trans-2-pentene-1,4-diol 
• 6790-38-1 1,2-epoxy-3-vinylpropane 
• 5604-51-3 Methyl-<2-phenoxy-cyclopropyl>-keton 
• 592-45-0 1,4-hexadiene 
• 39161-19-8 pent-3-en-1-ol 
• 25296-22-4 trans-1,4-dibromo-2-pentene 
• 5604-54-6 1-(2-phenoxy-cyclopropyl)-ethanol 
• 5604-66-0 1-(2-ethoxy-cyclopropyl)-ethanol 

Downstream Products

• 126232-82-4 (9E,12E)-Tetradeca-9,12-dien-1-ol 
• 122091-56-9 (-)-(R)-4-(p-tolyl)pentan-1-ol 
• 122091-57-0 (-)-(R)-4-(p-tolyl)pentanal 
• 942043-54-1 p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside 
• 1012064-99-1 C₂₅H₃₀O₅S 
• 942043-53-0 para-methylphenyl 4,6-O-benzylidene-3-O-para-methoxybenzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)

(Chemical Equation Presented) [cis-Ru(II)(dmp)2(H 2O)2]2+ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.

Synthesis of oxygen-containing compounds from 1,4-pentadiene

1,4-Pentadiene oxidation with pinane and cumene hydroperoxides was examined. The application of crude cumene hydroperoxide was shown to yield 90% 1,2-epoxypentene-4 at an oxidant conversion of over 95%. The isomerization of 1,2-epoxypentene-4 in the vapor phase at 290-330°C on lithium phosphate was studied. The rearrangement yielded 2,4-pentadiene-1-ol and unsaturated carbonyl compounds in a nearly 1:1 ratio at an epoxide conversion of 50%. Carbonyl compounds consisted mainly of pentenals with a different double-bond position. The results of the rearrangement show that the epoxide C-O bond heterolysis takes place mainly on the allyl group side.

Two-phase Hydroformylation of Buta-1,3-diene and Hydrocarbon Mixtures Containing Buta-1,3-diene

The two-phase hydroformylation of buta-1,3-diene with (HRh(CO)[P(m-C6H4SO3Na) 3]3) the Kuntz catalyst system with excess P(m-C6H4SO3Na)3) gives high yields of C5-monoaldehydes. Main product in this mixture is the reactive trans- and cis-pent-3-enal. In consecutive reactions the pent-3-enal is partially hydrogenated to n-pentanal, but also - favoured by the protolytic milieu of the two-phase reaction - aldol condensated to 2-propenylheptadienal. The hydrogenation product of the propenylheptadienal, 2-propylheptanol-1, is a good plasticizer alcohol with a wanted low vapour pressure. Especially promising is the two-phase hydroformylation of the unrefined C4-fraction of the naphtha pyrolysis: after a more than 95 per cent conversion of the buta-1,3-diene also more than 80 per cent of the n-but-1-ene in the C4-fraction is hydroformylated mainly to wanted n-pentanal. Less than 5-10% of the n-but-2-enes and the isobutene in the C4-fraction react under these conditions to oxo-products (2- and 3-methylbutanal). Acetylenic compounds in the C4-fraction are converted quantitatively into products.

Asymmetric hydroformylation of conjugated dienes catalyzed by chiral phosphine-phosphite-Rh(I) complex

Asymmetric hydroformylation of conjugated dienes has been investigated using (R,S)-BINAPHOS-Rh(I) complex as a catalyst [(R,S)-BINAPHOS = (R)-2-(diphenylphosphino)-1,1'-binaphthalen-2'-yl (S)-1,1'-binaphthalene-2,2'-diyl phosphite]. Optically active β,γ-unsaturated aldehydes were obtained in high regio- (78-94%) and enantioselectivities (80-97% ee) from 1-vinylcyclohexene, 4-methyl-1,3-pentadiene, and (E)-1-phenyl-1,3-butadiene. On the other hand, hydroformylation of 1,3-butadiene gave achiral product, (E)- and (Z)-3-pentenal, in up to 95% selectivity. (R)-(E)-2-Methyl-3-pentenal was formed as the major product from both (E)- and (Z)-1,3-pentadiene, but enantioselectivity of the reaction was low. Mechanistic aspects are also discussed.

Asymmetric hydroformylation of conjugated dienes catalysed by [(R)-2-diphenylphosphino-1,1′-dinaphthalen-2′-yl] [(S)-1,1′-dinaphthalene-2,2′-diyl]phosphite-rhodium(I)

Asymmetric hydroformylation of conjugated dienes such as vinylcyclohexene, (E)-phenyl-buta-1,3-diene and 4-methyl-penta-1,3-diene using BINAPHOS-RhI complexes as catalysts {(R,S)-BINAPHOS = [(R)-2-diphenylphosphino-1,1′-dinaphthalen-2′-yl] [(S)-1,1′-dinaphthalene-2,2′-diyl]-phosphite} gives optically active β,γ-unsaturated aldehydes in high regio- (81-91%) and enantio-selectivities (84-97% ee).

Investigation of Aliphatic Dienes by Chemical Ionization with Nitric Oxide

It is shown that the position of the double bond close to the hydrocarbon end of an aliphatic diene functionalized at C(1) can readily be determined by chemical ionization with NO+.Owing to the low abundance of the ions characteristic for the position of the other double bond, its localization may be difficult.Measurement of the chemical ionization (nitric oxide as reagent gas) spectra of the corresponding epoxides or collision activation studies can help.