5454-21-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 6729, 1990 DOI: 10.1021/ja00174a053Synthetic Communications, 22, p. 3109, 1992 DOI: 10.1080/00397919209409261

InChI:InChI=1/C14H20O2/c1-2-3-4-8-11-14(15)16-12-13-9-6-5-7-10-13/h5-7,9-10H,2-4,8,11-12H2,1H3

Upstream product

• 110-86-1 pyridine 
• 2528-61-2 Heptanoic acid chloride 
• 100-51-6 benzyl alcohol 
• 109-65-9 1-bromo-butane 
• 2495-35-4 benzylacrylate 
• 111-25-1 1-bromo-hexane 
• 106412-35-5 N-benzyloxycarbonyl-2-piperidone 
• 592-41-6 1-hexene 
• 201230-82-2 carbon monoxide 
• 122-56-5 tributyl borane 
• 111-14-8 oenanthic acid 
• 100-39-0 benzyl bromide 
• 110-54-3 hexane 
• 542-69-8 1-iodo-butane 

Relevant academic research and scientific papers

Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments

Most of the well-known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co-substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions.

Visible-light-initiated manganese-catalyzed Giese addition of unactivated alkyl iodides to electron-poor olefins

Herein, we report a mild protocol for direct visible-light-initiated Giese addition of unactivated alkyl iodides to electron-poor olefins (Michael acceptors) with catalysis by decacarbonyl dimanganese, Mn2(CO)10, an inexpensive earth-abundant-metal catalyst. This protocol is compatible with a wide array of sensitive functional groups and has a broad substrate scope with regard to both the alkyl iodide and the Michael acceptor.

Copper-Catalyzed Alkoxycarbonylation of Alkanes with Alcohols

Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the C sp3 ?H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields. Paraformaldehyde could also be applied for in situ alcohol generation by radical trapping, and moderate yields of the corresponding esters could be produced. Notably, this is the first report on copper-catalyzed alkoxycarbonylation of alkanes.

Metal-free radical oxidative alkoxycarbonylation and imidation of alkanes

A metal-free radical oxidative carbonylation of alkanes is demonstrated, yielding esters and imides by means of di-tert-butylperoxide as an oxidant. Various alkanes, alcohols and amides were compatible in this system generating the desired carbonyl products in up to 86% yields. We proposed a plausible radical cross-coupling process based on the preliminary mechanistic studies.

Oxidative Alkane C?H Alkoxycarbonylation

Directly utilizing a chemical feedstock to construct valuable compounds is an attractive prospect in organic synthesis. In particular, the combination of C(sp3)?H activation and oxidative carbonylation involving alkanes and CO gas is a promising and efficient method to synthesize carbonyl derivatives. However, due to the high C?H bond dissociation energy and low polarity of unactivated alkanes, the carbonylation of unactivated C(sp3)?H bonds still remains a great challenge. In this work, we introduce a palladium-catalyzed radical oxidative alkoxycarbonylation of alkanes to prepare numerous alkyl carboxylates. Various alkanes and alcohols were compatible, generating the desired products in up to 94 % yield. Remarkably, ethane, a constituent of natural gas, could be employed as a substrate under the standard reaction conditions. Preliminary mechanistic studies revealed a probable palladium-catalyzed radical process.

Multifunctional mesoporous silica catalyst

The present invention provides bifunctional silica mesoporous materials, including mesoporous silica nanoparticles (“MSN”), having pores modified with diarylammonium triflate and perfluoroaryl moieties, that are useful for the acid-catalyzed esterification of organic acids with organic alcohols.

Synthesis and applications of highly efficient, reusable, sulfonic acid group functionalized Broensted acidic ionic liquid catalysts

A variety of sulfonic acid group functionalized Broensted acidic ionic liquids (BAILs) catalysts were synthesized. Catalytic activities of BAILs were assessed using condensation and esterification reactions. Catalytic activities of BAILs were high when compared with H-ZSM-5, H-BETA, sulfonic acid functionalized SBA-15 catalyst. The Hammett acidity order determined from UV-visible spectroscopy of BAILs is consistent with their activity order observed in acid-catalyzed reactions. Recycling experiments suggests that these novel BAILs can be reused without significant loss in catalytic activity. Novel BAILs offers several attractive features such as low cost, high catalytic activity and recyclability.

Thermal decomposition of N-acyloxy-N-alkoxyamides a new HERON reaction

The HERON reaction has been observed in the thermal decompositions of N-acyloxy-N-alkoxyamides 1b, members of the class of anomeric amides. The N,N-bisoxo-substitution results in reduced amide resonance and this, combined with an nO-σ*NOAcyl anomeric destabilization of the N-OAcyl bond, results in their intramolecular rearrangement to anhydrides 42 and alkoxynitrenes 43 in competition with homolysis of the N-OAcyl bond to alkoxyamidyls 51. The primary HERON product alkoxynitrenes are scavenged by oxygen, giving a nitrate ester, in competition with a rearrangement to nitriles and dimerization to hyponitrites, leading, under the conditions, to alcohols and aldehydes. Persistent alkoxyamidyls most likely form a 1,3-diradical in a solvent-cage reaction, which cyclizes to 3,5-disubstituted-(5H)-1,4,2-dioxazoles 47. Substituent effects support this competition reaction. CSIRO 2010.

Nickel-catalyzed carboxylation of organozinc reagents with CO2

(Chemical Equation Presented) An efficient nickel catalyst system for the carboxylation of organozinc reagents with CO2 under very mild conditions has been developed. The catalyst system complements the conventional methods and enables the dire

Nickel-catalyzed 1,4-addition of trialkylboranes to α,β- unsaturated esters: Dramatic enhancement by addition of methanol

Equation presented Nickel catalyst systems for 1,4-addition of trialkylboranes to α,β-unsaturated esters have been developed. Addition of methanol was found to be essential for the alkylation reaction with 9-alkyl-9-BBNs.