6553-81-7

Usage

InChI:InChI=1/C11H20O2/c1-2-3-9-13-11(12)10-7-5-4-6-8-10/h10H,2-9H2,1H3

Upstream product

• 136-60-7 benzoic acid, butyl ester 
• 71-36-3 butan-1-ol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 221887-36-1 2,2,2-tribromoethyl cyclohexanecarboxylate 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 201230-82-2 carbon monoxide 
• 6830-84-8 N-methylcyclohexanecarboxamide 
• 37170-50-6 di(methyl)tert-butyl(n-butoxy)silane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1122-56-1 cyclohexylcarboxamide 
• 766-05-2 cyclohexane carbonitrile 
• 110-82-7 cyclohexane 
• 108-85-0 1-bromocyclohexane 
• 23054-48-0 N-(2-hydroxyethyl)cyclohexanecarboxamide 

Relevant academic research and scientific papers

Zr-MOF-808 as Catalyst for Amide Esterification

In this work, zirconium-based metal–organic framework Zr-MOF-808-P has been found to be an efficient and versatile catalyst for amide esterification. Comparing with previously reported homogeneous and heterogeneous catalysts, Zr-MOF-808-P can promote the reaction for a wide range of primary, secondary and tertiary amides with n-butanol as nucleophilic agent. Different alcohols have been employed in amide esterification with quantitative yields. Moreover, the catalyst acts as a heterogeneous catalyst and could be reused for at least five consecutive cycles. The amide esterification mechanism has been studied on the Zr-MOF-808 at molecular level by in situ FTIR spectroscopic technique and kinetic study.

IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway

An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.

Cobalt-Nanoparticles Catalyzed Efficient and Selective Hydrogenation of Aromatic Hydrocarbons

The development of inexpensive and practical catalysts for arene hydrogenations is key for future valorizations of this general feedstock. Here, we report the development of cobalt nanoparticles supported on silica as selective and general catalysts for such reactions. The specific nanoparticles were prepared by assembling cobalt-pyromellitic acid-piperazine coordination polymer on commercial silica and subsequent pyrolysis. Applying the optimal nanocatalyst, industrial bulk, substituted, and functionalized arenes as well as polycyclic aromatic hydrocarbons are selectively hydrogenated to obtain cyclohexane-based compounds under industrially viable and scalable conditions. The applicability of this hydrogenation methodology is presented for the storage of H2 in liquid organic hydrogen carriers.

Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas

A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.

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.

Cobalt-Catalyzed Esterification of Amides

The first cobalt-catalyzed amide activation of N-Boc-amides, and their conversion into esters, is reported here. This new methodology presents a very practical process that does not require an inert atmosphere, uses an inexpensive cobalt catalyst, and proceeds under mild reaction conditions. This catalytic system has a broad substrate scope and has been shown to be highly efficient, with catalyst loadings as low as 1 mol %.

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.

Cycloalkyl carboxylic acid ester compound preparation method

The present invention discloses a cycloalkyl formate compound preparation method, wherein in the presence of a palladium salt and a peroxide, a cycloalkane compound and an alcohol compound are dissolved in an organic solvent, the system is replaced by a carbon monoxide atmosphere, a reaction is performed for 16-24 h at a reaction temperature of 90-120 DEG C, and separation and purification are performed to obtain the cycloalkyl formate compound. According to the present invention, the used reactants are cheap and easy to obtain, the reaction conditions are simple, the atom economy is high, and the high-selectivity oxidation carbonylation reaction of the cycloalkane compound and the alcohol compound can be achieved so as to obtain the cycloalkyl formate compound; with the method, the precursor of the widely-used drug dicyclomine having treatment effects on intestines and stomach cramps and irritable bowel syndrome can be simply prepared; and the method has application potential in synthesis of drugs, natural products and the like.

Palladium-Catalyzed Alkoxycarbonylation of Unactivated Secondary Alkyl Bromides at Low Pressure

Catalytic carbonylations of organohalides are important C-C bond formations in chemical synthesis. Carbonylations of unactivated alkyl halides remain a challenge and currently require the use of alkyl iodides under harsh conditions and high pressures of CO. Herein we report a palladium-catalyzed alkoxycarbonylation of secondary alkyl bromides that proceeds at low pressure (2 atm CO) under mild conditions. Preliminary mechanistic studies are consistent with a hybrid organometallic-radical process. These reactions efficiently deliver esters from unactivated alkyl bromides across a diverse range of substrates and represent the first catalytic carbonylations of alkyl bromides with carbon monoxide.

Manganese(II)-Catalyzed Esterification of N-β-Hydroxyethylamides

A catalyst system of manganese with 2,2-bipyridine for amide alcoholysis of N-β-hydroxyethylamides is described. This protocol enabled selective cleavage of the amide bond through a mechanism involving sequential N,O-acyl rearrangement and transesterification.