1576-86-9

Upstream product

• 6158-85-6 5-ethyl-isotetronic acid 
• 33498-40-7 1,1-diethoxy-pent-2-ene 
• 6736-21-6 3-pentene-1,2-diol 
• 5604-66-0 1-(2-ethoxy-cyclopropyl)-ethanol 
• 2862-47-7 3-phenoxy-propenal 
• 925-90-6 ethylmagnesium bromide 
• 62084-18-8 4-pentene-2,3-diol 
• 7664-93-9 sulfuric acid 
• 591-93-5 1,4-Pentadiene 
• 1576-96-1 (E)-2-penten-1-ol 
• 73939-02-3 sodium dehydroacetic acid 
• 39595-61-4 1,1,3-triethoxypentane 
• 25296-22-4 trans-1,4-dibromo-2-pentene 
• 25073-25-0 trans-2-pentene-1,4-diol 

Downstream Products

• 626-98-2 pent-2-enoic acid 
• 439590-21-3 3-ethyl-5-phenyl-4-pentenal 
• 33580-08-4 Benzyldimethyl-4-(1.5-octadienyl)-ammonium 
• 1185751-85-2 (-)-3-(4',5'-dihydro-4'-methyl-5'-oxo-2'-phenyloxazol-4'-yl)pentanal 

Relevant academic research and scientific papers

Double Bond Stabilizing Abilities of Formyl, Carbo-tert-butoxy, and Carbomethoxy Substituents

Equilibrium constants for reactions of the type trans-MeCH=CHCH2COX trans-EtCH=CHCOX, where X is H, OMe, and O-t-Bu, have been determined in tert-butyl alcohol solution at various temperatures by using basic catalysts.These equilibrium constants for formation of the conjugated isomer, extrapolated to 25 deg C, are 24, 4.9, and 5.1 for the aldehyde, methyl ester, and tert-butyl ester, respectively.Possible explanations for the relative magnitudes of these equilibrium constants are discussed.

One-Step Bioconversion of Fatty Acids into C8-C9 Volatile Aroma Compounds by a Multifunctional Lipoxygenase Cloned from Pyropia haitanensis

The multifunctional lipoxygenase PhLOX cloned from Pyropia haitanensis was expressed in Escherichia coli with 24.4 mg·L-1 yield. PhLOX could catalyze the one-step bioconversion of C18-C22 fatty acids into C8-C9 volatile organic compounds (VOCs), displaying higher catalytic efficiency for eicosenoic and docosenoic acids than for octadecenoic acids. C20:5 was the most suitable substrate among the tested fatty acids. The C8-C9 VOCs were generated in good yields from fatty acids, e.g., 2E-nonenal from C20:4, and 2E,6Z-nonadienal from C20:5. Hydrolyzed oils were also tested as substrates. The reactions mainly generated 2E,4E-pentadienal, 2E-octenal, and 2E,4E-octadienal from hydrolyzed sunflower seed oil, corn oil, and fish oil, respectively. PhLOX showed good stability after storage at 4 °C for 2 weeks and broad tolerance to pH and temperature. These desirable properties of PhLOX make it a promising novel biocatalyst for the industrial production of volatile aroma compounds.

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Catalytic Reactions of Homo- and Cross-Condensation of Ethanal and Propanal

Abstract: Processes of catalytic homocondensation of propanal and its cross-condensation with ethanal and methanal in the presence of aniline and amino acids have been studied. The dependence of the conversion of the reactants and selectivity of the homo/heterocondensation process on the catalyst nature and temperature has been revealed. It has been shown that the maximum acrolein selectivity is reached in the case of using benzoyl-substituted derivatives in water, with the proportion of the products of further condensation decreasing. The selectivity for the ethanal homocondensation product 2-butenal decreases simultaneously as a result of the formation of linear and branched oligomers of successive condensation.

Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst

Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.

Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

Lipid-derived aldehyde degradation under thermal conditions

Nucleophilic degradation produced by reactive carbonyls plays a major role in food quality and safety. Nevertheless, these reactions are complex because reactive carbonyls are usually involved in various competitive reactions. This study describes the thermal degradation of 2-alkenals (2-pentenal and 2-octenal) and 2,4-alkadienals (2,4-heptadienal and 2,4-decadienal) in an attempt to both clarify the stability of aldehydes and determine new compounds that might also play a role in nucleophile/aldehyde reactions. The obtained results showed that alkenals and alkadienals decomposed rapidly in the presence of buffer and air to produce formaldehyde, acetaldehyde, and the aldehydes corresponding to the breakage of the carboncarbon double bonds: propanal, hexanal, 2-pentenal, 2-octenal, glyoxal, and fumaraldehyde. The activation energy of double bond breakage was relatively low (～25 kJ/mol) and the yield of alkanals (10-18%) was higher than that of 2-alkenals (～1%). All these results indicate that these reactions should be considered in order to fully understand the range of nucleophile/aldehyde adducts produced.

Thiol-functionalized fructose-derived nanoporous carbon as a support for gold nanoparticles and its application for aerobic oxidation of alcohols in water

Gold nanoparticles supported on thiol-functionalized fructose-derived nanoporous carbon (AuNPs@thiol-Fru-d-NPS) were found to be a simple bench-top, biocompatible, recyclable and selective catalytic system for the aerobic oxidation of various types of alcohols into their corresponding aldehydes and ketones at room temperature under the environmentally friendly conditions with excellent yields. Copyright

Protective groups for crossed aldol condensations

A process for protecting aldehydes and ketones in crossed aldol condensations where both aldols possess alpha-carbon hydrogens, comprising protecting the target aldol by forming an acetal or imine with an alcohol, glycol or primary amine which may contain electron-withdrawing groups, adding a base of sufficient strength to abstract a proton from the alpha-carbon of the acetal or imine and adding the second aldol to form the salt of the saturated hydroxy addition compound, thereby minimizing by-products, waste and separation difficulties, then forming the unsaturated addition compound and decomposing the acetal or imine with dilute acid. This process having the advantage that a ketone may be added to a protected aldehyde target to produce an aldehyde as a product which was not previously possible.

The atmospheric photolysis of E-2-hexenal, Z-3-hexenal and E,E-2,4-hexadienal

The atmospheric photolysis of E-2-hexenal, Z-3-hexenal and E,E-2,4-hexadienal has been investigated at the large outdoor European Photoreactor (EUPHORE) in Valencia, Spain. E-2-Hexenal and E,E-2,4-hexadienal were found to undergo rapid isomerization to produce Z-2-hexenal and a ketene-type compound (probably E-hexa-1,3-dien-1-one), respectively. Both isomerization processes were reversible with formation of the reactant slightly favoured. Values of j(E-2-hexenal)/j(NO2) = (1.80 ± 0.18) × 10-2 and j(E,E-2,4-hexadienal)/j(NO2) = (2.60 ± 0.26) × 10-2 were determined. The gas phase UV absorption cross-sections of E-2-hexenal and E,E-2,4-hexadienal were measured and used to derive effective quantum yields for photoisomerization of 0.36 ± 0.04 for E-2-hexenal and 0.23 ± 0.03 for E,E-2,4-hexadienal. Although photolysis appears to be an important atmospheric degradation pathway for E-2-hexenal and E,E-2,4-hexadienal, the reversible nature of the photolytic process means that gas phase reactions with OH and NO3 radicals are ultimately responsible for the atmospheric removal of these compounds. Atmospheric photolysis of Z-3-hexenal produced CO, with a molar yield of 0.34 ± 0.03, and 2-pentenal via a Norrish type I process. A value of j(Z-3-hexenal)/j(NO2) = (0.4 ± 0.04) × 10-2 was determined. The results suggest that photolysis is likely to be a minor atmospheric removal process for Z-3-hexenal. the Owner Societies.