20299-83-6

Usage

Class

Ketone derivative and a member of the piperidine class of compounds

Usage

Synthesis of pharmaceuticals
Synthesis of agrochemicals
Synthesis of other organic compounds

Potential Medicinal Properties

Role as a drug intermediate
Potential application in the treatment of various diseases

Physical State

Colorless liquid

Odor

Slightly sweet

Common Use

Reagent in chemical reactions and organic synthesis

Upstream product

• 215667-89-3 3-iodo-1-piperidino-1-propanone 
• 110-89-4 piperidine 
• 14273-09-7 1-ethoxy-1-octyne 
• 124-07-2 Octanoic acid 
• 124-13-0 Octanal 
• 111-64-8 n-octanoic acid chloride 
• 110-91-8 morpholine 
• 111-87-5 octanol 
• 111-11-5 methyl octanate 
• 59147-44-3 β-chloropropionyl piperidide 
• 72665-98-6 n-pentylzinc iodide 
• 90154-52-2 3-bromo-1-(piperidin-1-yl)propan-1-one 
• 14402-93-8 dipentylzinc 
• 135676-74-3 1,5-Dioctanoyl-[1,3,5]triazinane-2,4-dione 

Relevant academic research and scientific papers

Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification

Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.

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.

Antifungal agent, antimildew method using the same, and a method using the growth inhibiting growth inhibiting agent

PROBLEM TO BE SOLVED: To provide a mould-proofing agent exhibiting highly mould-proofing effect and enabling its own production cost to be reduced, and to provide a mould-proofing method using the same.SOLUTION: The mould-proofing agent is provided, which includes an amide compound represented by general formula (1) as an active ingredient. In general formula (1), either one of Xand Xis 3-7C branched alkyl, the other being H; alternatively, the Xand Xare optionally bound to each other to form a (substituted) saturated or unsaturated 5- or 6-membered ring; Y is a 4-7C alkylene group; and Z is methyl or vinyl.

Dehydrogenative amide synthesis from alcohol and amine catalyzed by hydrotalcite-supported gold nanoparticles

Hydrotalcite-supported nano-gold (Au/HT) was found to be a highly efficient heterogeneous catalyst for the dehydrogenative synthesis of amide from alcohol and amine. Amines and alcohols with different structures could be converted into the amides under mild reaction conditions with up to 98% isolated yields. Mechanism exploration suggested that ester might be the reaction intermediate.

Synthesis of amides and lactams in supercritical carbon dioxide

(Chemical Equation Presented) Supercritical carbon dioxide can be employed as an environmentally friendly alternative to conventional organic solvents for the synthesis of a variety of carboxylic amides. The addition of amines to ketenes generated in situ via the retro-ene reaction of alkynyl ethers provides amides in good yield, in many cases with ethylene or isobutylene as the only byproducts of the reaction. Reactions with ethoxy alkynes are performed at 120-130°C, whereas tert-butoxy derivatives undergo the retro-ene reaction at 90°C. With the exception of primary, unbranched amines, potential side reactions involving addition of the amines to carbon dioxide are not competitive with the desired C-N bond-forming reaction. The amide synthesis is applicable to the preparation of β-hydroxy and β-amino amide derivatives, as well as amides bearing isolated carbon-carbon double bonds. Preliminary experiments aimed at developing an intramolecular variant of this process to afford macrolactams suggest that the application of CO2/co-solvent mixtures may offer advantages for the synthesis of large-ring compounds.

Acyl transfer catalysis with 1,2,4-Triazole anion

1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.

Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides

In the presence of Bu4NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu4NI. The bicyclic secondary diorganozinc 6 prepared via boron-zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products.

New efficient nickel-catalyzed cross-coupling reaction between two Csp3 centers

The presence of a remote unsaturation (double bond, carbonyl group, cyano group) in an alkyl halide facilitates its cross-coupling reaction with various diorganozincs in the presence of Ni(acac)2 (7.5-10 mol % in THF/NMP mixtures). These results were used to develop a new general cross-coupling reaction between functionalized diorganozincs and alkyl iodides using m- or p-trifluoromethylstyrene as a reaction promotor and Ni(acac)2 as a catalyst (7.5-10 mol %; -35 °C, 5-10 h) leading to a broad range of polyfunctional cross-coupling products.

An efficient nickel-catalyzed cross-coupling between sp3 carbon centers

Since the pioneering work of Wurtz, cross-couplings between sp3 carbon centers have had the reputation of being difficult. In the presence of a catalytic amount of m-trifluoromethylstyrene, an efficient cross-coupling reaction takes place between polyfunctional primary alkyl iodides and diorganozinc compounds [Eq. (a)] to give a general catalytic cross-coupling between sp3 carbon centers. Piv = pivaloyl; Pent = pentyl; acac = acetalacetonate; NMP = N-methylpyrrolidone.

Preparation and Characterization of 1,5-Diacyl-2,4-dioxohexahydro-1,3,5-triazines with Higher Acyl Groups

The title compounds were prepared from 2,4-dioxohexahydro-triazine (DHT) and the corresponding acid chlorides in the presence of sulphuric acid.They are active acylating agents against piperidine in dioxane as the solvent.Only the diacyl derivatives of DHT with acyl chain lengths up to C6 react with aqueous solutions of sodium perborate forming the corresponding peroxy acids.