6939-75-9

Usage

Chemical Properties

clear yellow liquid

InChI:InChI=1/C12H14O3/c1-10(13)7-8-12(14)15-9-11-5-3-2-4-6-11/h2-6H,7-9H2,1H3

Upstream product

• 123-76-2 levulinic acid 
• 100-51-6 benzyl alcohol 
• 108-22-5 Isopropenyl acetate 
• 38447-66-4 acetyl phenyl selenide 
• 2495-35-4 benzylacrylate 
• 100-44-7 benzyl chloride 
• 5396-89-4 benzyl acetoacetate 
• 501-53-1 benzyl chloroformate 
• 81867-37-0 benzyl iodoacetate 
• 591-12-8 5-methyl-2-furanone 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 5437-45-6 Benzyl bromoacetate 
• 52267-51-3 benzyl diazoacetate 
• 67-64-1 acetone 

Downstream Products

• 139915-21-2 phenylmethyl E-4-oxopent-2-enoate 
• 344237-15-6 (6-tert-Butyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetic acid benzyl ester 
• 343840-38-0 (5-Methoxy-2,4,6-trimethyl-1H-indol-3-yl)-acetic acid benzyl ester 
• 344238-56-8 [2-Methyl-5-(1,1,2,2-tetrafluoro-ethoxy)-1H-indol-3-yl]-acetic acid benzyl ester 
• 57711-61-2 Benzyl-3-acetoxypropionat 
• 54614-97-0 4-ethylenedioxypentanoic acid phenylmethyl ester 
• 469886-49-5 (4S)-2-(2-benzyloxycarbonylethyl)-4-(tert-butyldiphenylsilyloxymethyl)-2-methyloxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis method of acid hydrolysis compound and method for solid-phase coupling of glycoprotein, solid-phase modification derivation and glycopeptide enrichment by using acid hydrolysis compound

The invention discloses a synthesis method of an acid hydrolysis compound and a method for solid-phase coupling of glycoprotein, solid-phase modification derivation and glycopeptide enrichment by using the acid hydrolysis compound, and the synthesis method comprises the following steps: firstly, synthesizing a compound 6 with dioxolane, amino and carboxyl functional groups, and then carrying out reductive amination reaction on the compound and silica gel with amino to obtain a compound 7 which is covalently bound with silica gel, carrying out a Schiff-base reaction to covalently bind malonaldehyde with the compound 7 to obtain a compound 8, covalently binding the compound 8 with glycoprotein or glycopeptide to form a compound 9, incubating the treated glycopeptide with an acid solution, and carrying out primary hydrolysis elution in dioxolane at room temperature to obtain marked glycopeptide 10. The method has important significance in research on changes of sialoglycoprotein or glycopeptide in various diseases and the like.

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Solvent-free transesterification of methyl levulinate and esterification of levulinic acid catalyzed by a homogeneous iron(III) dimer complex

Levulinic acid esters MeC(O)CH2CH2CO2R (LAE) are emerging bio-based chemicals used as solvents, additives and plasticizers. In this work a variety of levulinates (R= n-butyl, n-hexyl, n-octyl, 2-ethylhexyl, geranyl, 2-ethoxyethyl, benzyl, 2-octyl, cyclohexyl, menthyl) is obtained from the solvent-free transesterification of methyl levulinate (ML) and esterification of levulinic acid (LA), catalyzed by a dimeric complex of iron(III). The results are competitive with the few related reports of literature mainly based on heterogeneous catalysis. This first systematic study based on a homogeneous catalytic system therefore represents a significant extension within the field of biomass valorization.

Acidic ion functionalized N-doped hollow carbon for esterification of levulinic acid

Acidic ion functionalized N-doped hollow carbon (NHC-[C4N][SO3CF3]) has been successfully synthesized by quaternization of N-doped hollow carbon (NHC) with 1,4-butanesultone, followed by ion exchange with trifluoromethanesulfonic acid. The catalyst was characterized by Fourier transform infrared (FT-IR), scanning electron microscopy (SEM), acid-base titration techniques and other methods. A hollow spherical catalyst with regular morphology, high acid density (2.72 mmol g-1) and good stability was obtained. Various characterizations showed that NHC-[C4N][SO3CF3] possesses abundant nanopores (3.41 nm), large Brunauer-Emmett-Teller (BET) surface area (154 m2 g-1) and strong and controllable Br?nsted acid sites. The as-prepared NHC-[C4N][SO3CF3] was then used for the acid-catalyzed esterification of levulinic acid with ethanol. At the optimum conditions, the highest conversion of levulinic acid reached 94.17% and high conversion was maintained after recycling four times. Further investigation of the catalytic activity in the esterification of different aliphatic and aromatic alcohols with levulinate was carried out, showing good results.

Photoredox-Catalyzed α-C(sp3)-H Activation of Unprotected Secondary Amines: Facile Access to 1,4-Dicarbonyl Compounds

A photoredox-catalyzed α-C(sp3)-H activation approach of unprotected secondary amines is reported. Such transformations provide facile access to various 1,4-dicarbonyl compounds using readily available amines and α,β-unsaturated compounds as feedstocks under air conditions. The substrate scope of this method is broad, and a wide array of functional groups are tolerated.

5-(PYRIDIN-3-YL)OXAZOLE ALLOSTERIC MODULATORS OF M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

Provided are 5-(pyridin-3-yl) oxazole compounds, the compositions comprising these compounds and the uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

Why Cyclopropanation is not Involved in Photoinduced α-Alkylation of Ketones with Diazo Compounds

Diazo compounds are widely used reagents in organic synthesis. Direct photolysis leads to singlet carbenes whereas, in the presence of a photosensitizer, carbenes in the triplet state are generated. However, their reactivity under light irradiation remains poorly understood. Herein, we report photocatalytic, direct alkylation of enamines, generated from ketones, with diazo esters in the presence of free-base porphyrins acting as photoredox catalysts. Based on the experimental and theoretical studies, we propose a plausible mechanism involving generation of an enamine radical cation that subsequently reacts with diazo compounds giving the radical thus excluding the controversial cyclopropanation–ring opening pathway.

Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group

We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence of fluoride anions or Lewis acids. A variety of silyl enol ethers, α-bromoketones, α-bromoesters, and α-bromoamides were applied to this system to produce the coupling compounds.

Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: General method for the synthesis of anhydrides and esters

The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R1OCO)2O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R1OH) as the solvent, leads to the esters RCOOR1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO)2O], R1OH and carbon dioxide. The esters arise from the attack of the alcohols on the anhydrides. Exploiting the lesser reactivity of tert-butyl alcohol in comparison with other alcohols, a clean synthesis of both carboxylic anhydrides and esters has been set up. In the former reaction, an acid/Boc2O molecular ratio of 2:1 leads to the anhydride in good to excellent yields, depending on the stability of the resulting anhydride to the usual workup conditions. In the latter reaction, stoichiometric mixtures of the acid and Boc2O are allowed to react with a twofold excess of a primary alcohol, secondary alcohol or phenol (R 2OH) to give the corresponding esters (RCOOR2). Purification of the products is particularly easy since all byproducts are volatile or water soluble. A very easy chromatography is required only in the case of nonvolatile alcohols. A broad variety of sensitive functional groups is tolerated on both the acid and the alcohol, in particular a high chemoselectivity is observed. In fact, no transesterification processes occur with the acid-sensitive acetoxy group and methyl esters. Georg Thieme Verlag Stuttgart.

Preparation of levulinic acid esters from alpha-angelica lactone and alcohols

The present invention relates to a process for producing levulinic acid esters from α-angelica lactone and alcohols in the presence of a basic catalyst. In addition, a method is described herein for producing fuel or fuel additives comprising levulinic acid esters produced from α-angelica lactone and alcohol. In addition, compositions are described comprising levulinic acid esters for use as fuel or fuel additives.