534-59-8

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C7H12O4/c1-2-3-4-5(6(8)9)7(10)11/h5H,2-4H2,1H3,(H,8,9)(H,10,11)/p-2

Upstream product

• 543-59-9 1-Chloropentane 
• 1822-71-5 n-pentylsodium 
• 109-66-0 pentane 
• 71-43-2 benzene 
• 10051-44-2 sodium caproate 
• 1623-99-0 phenyl sodium 
• 109-65-9 1-bromo-butane 
• 996-82-7 sodium diethylmalonate 
• 7391-39-1 ethyl 2-cyanohexanoate 
• 151-50-8 potassium cyanide 
• 124-38-9 carbon dioxide 
• 2875-37-8 pentyl potassium 
• 57742-51-5 5-butyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 133-08-4 diethyl butylmalonate 

Downstream Products

• 106270-20-6 2-butyl-3t-(3-nitro-phenyl)-acrylic acid 
• 101276-92-0 2-butyl-3t-(4-isopropyl-phenyl)-acrylic acid 
• 115034-10-1 butyl-malonic acid bis-(2,5-dimethyl-phenyl ester) 
• 115034-12-3 butyl-malonic acid bis-(3,4-dimethyl-phenyl ester) 
• 7391-62-0 5-Butyl-1,3-dimethylbarbituric acid 
• 616-06-8 2-amino-hexanoic acid 
• 29671-30-5 2-chlorohexanoic acid 
• 142-62-1 hexanoic acid 
• 15719-64-9 methylammonium carbonate 
• 100972-15-4 2-butyl-3t-(2-methoxy-phenyl)-acrylic acid 
• 101868-66-0 butyl-malonic acid bis-(2,4-dichloro-phenyl ester) 
• 3144-54-5 4-hexanoylresorcinol 
• 1148-75-0 5-butyl-2-phenyl-[1,3]oxazine-4,6-dione 
• 1157-51-3 4-acetoxy-5-butyl-2-phenyl-[1,3]oxazin-6-one 

Relevant academic research and scientific papers

Xanthenylacetic Acid Derivatives Effectively Target Lysophosphatidic Acid Receptor 6 to Inhibit Hepatocellular Carcinoma Cell Growth

Despite the increasing incidence of hepatocellular carcinoma (HCC) worldwide, current pharmacological treatments are still unsatisfactory. We have previously shown that lysophosphatidic acid receptor 6 (LPAR6) supports HCC growth and that 9-xanthenylacetic acid (XAA) acts as an LPAR6 antagonist inhibiting HCC growth without toxicity. Here, we synthesized four novel XAA derivatives, (±)-2-(9H-xanthen-9-yl)propanoic acid (compound 4 – MC9), (±)-2-(9H-xanthen-9-yl)butanoic acid (compound 5 – MC6), (±)-2-(9H-xanthen-9-yl)hexanoic acid (compound 7 – MC11), and (±)-2-(9H-xanthen-9-yl)octanoic acid (compound 8 – MC12, sodium salt) by introducing alkyl groups of increasing length at the acetic α-carbon atom. Two of these compounds were characterized by X-ray powder diffraction and quantum mechanical calculations, while molecular docking simulations suggested their enantioselectivity for LPAR6. Biological data showed anti-HCC activity for all XAA derivatives, with the maximum effect observed for MC11. Our findings support the view that increasing the length of the alkyl group improves the inhibitory action of XAA and that enantioselectivity can be exploited for designing novel and more effective XAA-based LPAR6 antagonists.

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions

Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.

Exploring the Promiscuous Enzymatic Activation of Unnatural Polyketide Extender Units in Vitro and in Vivo for Monensin Biosynthesis

The incorporation of new-to-nature extender units into polyketide synthesis is an important source for diversity yet is restricted by limited availability of suitably activated building blocks in vivo. We here describe a straightforward workflow for the biogenic activation of commercially available new-to-nature extender units. Firstly, the substrate scope of a highly flexible malonyl co-enzyme A synthetase from Streptomyces cinnamonensis was characterized. The results were matched by in vivo experiments in which the said extender units were accepted by both the polyketide synthase and the accessory enzymes of the monensin biosynthetic pathway. The experiments gave rise to a series of predictable monensin derivatives by the exploitation of the innate substrate promiscuity of an acyltransferase and downstream enzyme functions.

Copper-catalyzed intermolecular chloro- and bromotrifluoromethylation of alkenes

A highly practical copper-catalyzed intermolecular halotrifluoromethylation of alkenes has been developed under mild reaction conditions. A variety of Cl/Br-containing trifluoromethyl derivatives were directly synthesized from a wide range of alkenes, including electron-deficient and unactivated alkenes.

Synthesis, antibacterial activity, and biological evaluation of formyl hydroxyamino derivatives as novel potent peptide deformylase inhibitors against drug-resistant bacteria

Peptide deformylase (PDF) has been identified as a promising target for novel antibacterial agents. In this study, a series of novel formyl hydroxyamino derivatives were designed and synthesized as PDF inhibitors and their antibacterial activities were evaluated. Among the potent PDF inhibitors (1o, 1q, 1o′, 1q′, and 1x), in vivo studies showed that compound 1q possesses mild toxicity, a good pharmacokinetic profile and protective effects. The good in vivo efficacy and low toxicity suggest that this class of compounds has potential for development and use in future antibacterial drugs.

Organocatalytic enantioselective transient enolate protonation in conjugate addition of thioacetic acid to a-substituted n-acryloyloxazolidinones

Organocatalytic conjugate addition of thioacetic acid to a series of a-substituted N-acryloyloxazolidin-2- ones followed by enantioselective protonation has been studied in the presence of thiourea catalysts derived from cinchona alkaloids. Conjugate addition/protonation adducts have been obtained up to 97% ee and high yields. The methodology could serve as an easy and practical route to the syntheses of useful biologically active molecules.

Production of peroxycarboxylic acids

Provided are various methods, systems and reactors for producing peroxycarboxylic acid compositions, such as non-equilibrium compositions of peracetic acid, for example. The methods and systems relate to electrolytic generation of hydrogen peroxide or peroxide ions in a reactor, wherein the generated materials are reacted with an acetyl donor to form peracetic acid. In an embodiment, a source of alkali metal ions is provided to an anode chamber such that the ratio of concentrations of the alkali metal ions to protons in the anode chamber of a reactor is greater than 1.