25714-71-0Relevant articles and documents
Assembly of tunable supramolecular organometallic catalysts with cyclodextrins
Leclercq, Loic,Schmitzer, Andreea R.
, p. 3442 - 3449 (2010)
Methylated-β-CDs were used to activate a catalyst by ligand solution trapping, to form second-sphere coordination by ligand complexation, and to increase the regioselectivity of biphasic and homogeneous hydroformylation reactions. Different methylation degrees of the β-CD allow assembly of hydrophobic or hydrophilic catalysts that can be employed in homogeneous or biphasic hydroformylation reactions.
3-Hydroxypropionaldehyde (3-HPA) quantification by HPLC using a synthetic acrolein-free 3-hydroxypropionaldehyde system as analytical standard
Burgé,Flourat,Pollet,Spinnler,Allais
, p. 92619 - 92627 (2015)
HPLC-based quantification of 3-HPA using a synthetic acrolein-free 3-HPA standard obtained from commercially available 1,2,4-butanetriol through a straightforward and easy synthetic process has advantages over previous colorimetric methods of easier and safer implementation, and greater specificity. This HPLC method is very simple to implement in a lab, does not need any extra handling of the sample to be analyzed, and is suitable even in the presence of other aldehydes and 3-HPA derivatives, provided that the latter do not have similar retention times.
Three-component reductive alkylation of 2-hydroxy-1,4-naphthoquinones with lactols
Kim, Eliana E.,Onyango, Evans O.,Pace, Jennifer R.,Abbot, Timothy M.,Fu, Liangfeng,Gribble, Gordon W.
, p. 864 - 867 (2016)
Lactols II, obtained by DIBAL reduction of their corresponding lactones I, in equilibrium with their hydroxyaldehyde tautomers III were used in a three-component reductive alkylation with 2-hydroxy-1,4-naphthoquinone to give a series of 3-alkylated 2-hydroxy-1,4-naphthoquinone derivatives IV.
Catalytic Oxidation of Tetrahydrofuran in the Presence of Transition Metal Complexes under Aerobic Conditions
Shi, Min
, p. 592 - 593 (1998)
Upon stirring a THF solution of a transition metal under an aerobic atmosphere, γ-butyrolactone and a small amount of lactol and 4-hydroxybutyraldehyde are formed; the turnover number of this catalytic oxidation process can reach 150 when lrCl(CO)(PPh3)2 is used.
Intramolecular oxygen radical additions to α,β-unsaturated esters. Diastereoselective tandem cyclofunctionalization and hydrogen transfer reactions
Guindon, Yvan,Denis, Real C.
, p. 339 - 342 (1998)
The efficiency of a tandem process featuring an oxy radical cyclization and hydrogen transfer reaction of the resultant carbon-based radical has been demonstrated. This methodology affords 2,3-trans-disubstituted tetrahydrofurans by creating two new contiguous stereogenic centers with high levels of 1,2-induction in each step.
Synthesis of (E)-α-hydroxyethyl-α,β-unsaturated aldehydes by the reaction of tetrahydrofuran and aromatic aldehydes
Shi, Yong-Sen,Liu, Jian-Feng,Wu, Xiao-Lan,Ke, De-Hong,Xu, Sheng
supporting information, (2021/08/13)
Although α-functionalized α,β-unsaturated aldehydes have important applications in biomedicine, there are few reports on their synthesis. In this article, a new domino reaction for the synthesis of (E)-α-hydroxyethyl-α,β-unsaturated aldehydes was introduced, in which tetrahydrofuran (THF) used as carbonyl block. The first step is an oxidation of THF to 2-hydroxytetrahydrofuran (HTHF) and then it was condensed with ethanolamine under acid catalysis to obtain imine intermediate, which was further isomerized to enamines and used as nucleophiles to attack aldehydes. This is a simple and efficient way for the preparation of (E)-α-hydroxyethyl-α,β-unsaturated aldehydes with notable advantages of a simple procedure, widespread availability of the substrates.
Catalytic Selective Oxidation of Primary and Secondary Alcohols Using Nonheme [Iron(III)(Pyridine-Containing Ligand)] Complexes
Caselli, Alessandro,Gallo, Emma,Panza, Nicola,Rizzato, Silvia,Tseberlidis, Giorgio,di Biase, Armando
supporting information, p. 6635 - 6644 (2020/10/30)
The selective oxidation of different primary and secondary alcohols to carbonyl compounds by hydrogen peroxide was found to be catalyzed in conversion ranging from good to excellent by an iron(III) complex of a pyridine-containing macrocyclic ligand (Pc-L), without the need of any additive. The choice of the counteranion (Cl, Br, OTf) appeared to be of fundamental importance and the best results in terms of selectivity (up to 99 %) and conversion (up to 98 %) were obtained using the well-characterized [Fe(III)(Br)2(Pc-L)]Br complex, 4c. Magnetic moments in solid-state, also confirmed in solution ([D6]DMSO) by Evans NMR method, were calculated and point out to an iron metal center in the high spin state of 5/2. The crystal structure shows that the iron(III) center is coordinated by the four nitrogen atoms of the macrocycle and two bromide anions to form a distorted octahedral coordination environment. The catalytic oxidation of benzyl alcohol in acetonitrile was found occurring with better conversions and selectivities than in other solvents. The reaction proved to be quite general, tolerating aromatic and aliphatic alcohols, although very low yields were obtained for terminal aliphatic alcohols. Preliminary mechanistic studies are in agreement with a catalytic cycle promoted by a high-spin iron complex.
Tweaking the acid-sensitivity of transiently thermoresponsive Polyacrylamides with cyclic acetal repeating units
De Geest, Bruno G.,Van Herck, Simon
, (2020/03/26)
Merging the characteristics of thermoresponsive and stimuli-degradable polymers yields so-called transiently thermoresponsive polymers, which can find application for the design of injectable gels, nanoparticles, etc. within a biomedical context. Among these polymers, only a limited number is reported which shows selective degradation under mild acidic conditions. However, extension of the library of transiently thermoresponsive polymers is desired to broadening the biomaterials toolbox to suit specific needs. Three monomers were developed by modification of 2-hydroxyethylacrylamide (HEAm) via tetrahydropyranylation or -furanylation with 3,4-dihydro-2H-pyran (DHP), 2,3-dihydrofuran (DHF) or 2,3-dihydro-5-methylfuran (MeDHF). The presence of an acetal or ketal bond provided the monomers a pH-dependent hydrolysis behavior ranging from minutes to days. RAFT polymerisation allowed for the construction of homopolymers with temperature responsive behavior and pH-dependent hydrolysis which was strongly influenced by nature of the monomeric repeating units.
PRODUCING BDO VIA HYDROFORMYLATION OF ALLYL ALCOHOL MADE FROM GLYCERIN
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Paragraph 0050, (2019/09/06)
A method including hydroformylating, with syngas, allyl alcohol in an allyl alcohol feed, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a 1,4-butanediol (BDO) product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, bio-allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product; and removing a byproduct of the production of the bio-allyl alcohol prior to hydroformylating the bio-allyl alcohol and/or from the BDO-product.
Preparation method for 4-oxobutyl acetate
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Paragraph 0019, (2018/07/30)
The invention relates to a preparation method for 4-oxobutyl acetate. The method comprises the following steps: a, adding 2,3-dihydrofuran, water, acetic acid and a solid acid catalyst into an organicsolvent under the protection of an inert gas, performing heating, performing stirring for a reaction, and after the reaction is completed, performing filtration; and b, performing reduced-pressure distillation on the filtrate obtained in the step a to obtain the 4-oxobutyl acetate. According to the method provided by the invention, raw materials are cheap and environmentally friendly, two steps of reactions in the reaction process are performed at the same time, an intermediate does not need to be separated, the process is simple, and the method is convenient to operate.
