3506-84-1

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(1-naphthyl)butan-2-one is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that are integral to the development of new drugs.
Used in Organic Chemistry Reactions:
As a reagent in organic chemistry, 4-(1-naphthyl)butan-2-one is employed to facilitate various chemical reactions, including the synthesis of organic compounds and the modification of existing ones, thereby expanding the range of possible chemical products.
Used in Chemical Production:
4-(1-naphthyl)butan-2-one is used as a precursor in the production of a variety of compounds, highlighting its importance in the chemical industry. Its role in the synthesis of other chemicals underscores its value as a foundational component in the creation of diverse chemical products.
Used in Industrial Applications:
4-(1-naphthyl)butan-2-one's industrial applications are broad, reflecting its adaptability and the demand for its unique properties in various sectors. Its use in different industries is a testament to its multifaceted utility and the reliance on its chemical characteristics for specific processes and products.

InChI:InChI=1/C14H14O/c1-11(15)9-10-13-7-4-6-12-5-2-3-8-14(12)13/h2-8H,9-10H2,1H3

Upstream product

• 598-32-3 2-hydroxy-3-butene 
• 99747-74-7 1-naphthyl triflate 
• 141-97-9 ethyl acetoacetate 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 27309-70-2 tris(1-naphthyl)stilbane 
• 78-94-4 methyl vinyl ketone 
• 90-11-9 1-Bromonaphthalene 
• 88022-93-9 1-(ethoxycarbonyl)-1-(1-naphthylmethyl)-2-propanone 
• 876-27-7 4-chlorophenyl acetate 
• 66920-76-1 (3E)-4-(naphthalen-1-yl)but-3-en-2-ol 
• 256462-17-6 methyl 4-(1-naphthyl)-2-oxobutyrate 
• 6833-19-8 1-naphthanilide 
• 676-58-4 methylmagnesium chloride 
• 197898-61-6 N-methoxy-N-methyl-3-(naphthalen-1-yl)propanamide 

Downstream Products

• 2531-84-2 2-methylphenathrene 
• 80749-36-6 2-acetamidophenyl 1-naphthylmethyl ketone 
• 80749-39-9 2-aminophenyl 1-naphthylmethyl ketone 
• 1634-09-9 1-butylnaphthalene 

Relevant academic research and scientific papers

REACTIVITY OF LOW ENERGY EXCITED STATES. MECHANISTIC AND EXPLORATORY ORGANIC PHOTOCHEMISTRY

The photochemistry of 3-methyl-3-(1'-naphthyl)-1-butene was investigated.Direct irradiation led to 1,1-dimethyl-2-(1'-naphthyl)cyclopropane as a primary photoproduct and 2-methyl-4-(1'-naphthyl)-1-butene as a secondary product.The quantum yield for the formation of the cyclopropane was 0.037.The corresponding triplet reaction was less efficient, with a quantum yield of 0.012, but still afforded the same product.The excited singlet rearrangement rate was determined by single photon counting; this proved to be 1kr = 5.9 x 105 sec-1.The total rate of S1 decay was determined as 1.59 x 107 sec-1 with a lifetime of 62.9 nsec.Thus, the lifetime of this rearranging system is quite similar to that of simple 1-alkylnaphthalenes (ca 65 nsec); and, the rate of di-?-methane rearrangement is the slowest known.Finally, the rate of radiationless decay of the singlet was found to be almost temperature independent between room temperature and 77 K.

The Heck reaction of allylic alcohols catalysed by an N-heterocyclic carbene-Pd(ii) complex and toxicity of the ligand precursor for the marine benthic copepod: Amphiascoides atopus

The palladium-catalysed reaction of aryl halides and allylic alcohols is an attractive method for obtaining α,β-unsaturated aldehydes and ketones, which represent key intermediates in organic synthesis. In this context, a 1,2,3-triazol-5-ylidene (aNHC)-based palladium(ii) complex formed in situ has been found to be a selective catalyst for the syntheses of building blocks from the corresponding aryl halides and allylic alcohols, with yields ranging from 50% to 90%. The lack of toxic effects of the ligand precursor (1,2,3-triazolium salt) of the palladium(ii) complex for the harpacticoid copepod Amphiascoides atopus allowed us to contrast the efficiency of the catalytic system with the potential impact of the principal waste chemical in global aquatic ecosystems, which has not been previously addressed.

Hydrogen-transfer reduction of α,β-unsaturated carbonyl compounds catalyzed by naphthyridine-functionalized N-heterocyclic carbene complexes

Substitution of silver complex of 2-chloro-7-(mesitylimidazolylidenylmethyl)naphthyridine (NpNHC) with palladium(II), rhodium(I) and iridium(I) metal precursors provided [Pd(C,N-NpNHC)(η3-allyl)](BF4) (5), RhCl(COD)(C-NpNHC) (6a) and IrCl(COD)(C-NpNHC) (6b), respectively. Abstraction of chloride from 6a and 6b with AgBF4 provided the chelation complexes [Rh(COD)(C,N-NpNHC)](BF4) (7a) and Ir(COD)(C,N-NpNHC)(BF4) (7b), respectively. All complexes were characterized using NMR and elemental analyses and the structural details of 5 and 6a were further confirmed using X-ray crystallography. In catalytic activity studies, complex 5 was found to be an effective catalyst in the hydrogen-transfer reduction of α,β-unsaturated carbonyl compounds into the corresponding saturated carbonyl compounds.

A Hantzsch Amido Dihydropyridine as a Transfer Hydrogenation Reagent for α,β-Unsaturated Ketones

An improved synthesis of the bis-methylamido Hantzsch dihydropyridine is described. The Hantzsch amide is demonstrated to be an effective transfer hydrogenation reagent using α,β-unsaturated ketones as the test case. Unreacted Hantzsch amide and the bis-methylamidopyridine byproduct are effectively removed by extraction in contrast to the commonly used Hantzsch diethyl ester. Several examples are given with the reaction being more effective for conjugated aromatic substrates than for aliphatics.

Preparation, hydrogen bonds, and catalytic activity in metal-promoted addition of arylboronic acids to enones of a rhodium complex containing an NHC ligand with an alcohol function

The complex RhCl(COD){3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazol-2- ylidene} has been prepared by reaction of the dimer [Rh(μ-OMe)(COD)] 2 with 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride and characterized by X-ray diffraction analysis. The structure reveals that 75% of the molecules are associated through intermolecular O-H...Cl hydrogen bonds between the OH group of the NHC substituent of one molecule and the chloride ligand of the adjacent molecule. This complex catalyzes the addition of arylboronic acids to cyclic and acyclic enones in anhydrous toluene. The alcohol function of the substituent of the NHC ligand plays the role assigned to water in previous cases.

The Heck reaction of allylic alcohols catalysed by an air-stable phosphinito complex of palladium(II)

The Heck coupling of aryl bromides with primary and secondary allylic alcohols, performed in the presence of an air-stable- phosphinito complex of palladium(II), produced the corresponding carbonyl compounds. Reactions with tertiary allylic alcohols under the same conditions generated the aromatic conjugated alcohols. Georg Thieme Verlag Stuttgart · New York.

Chemoselective conjugate reduction of α,β-unsaturated ketones catalyzed by rhodium amido complexes in aqueous media

Although a notable feature of Noyori's Ru-TsDPEN complex is that the transfer hydrogenation reaction is highly chemoselective for the C-O functional group and tolerant of alkenes, our early report indicated that the chemoselectivity could be switched from C-O to C-C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones. Now we have found that a variety of α,β-unsaturated ketones, even without other electron-withdrawing functional groups, could be reduced on the alkenic double bonds with high selectivities employing amido-rhodium hydride complex in aqueous media, and up to 100% chemoselectivity has been achieved. It is notable that the chemoselectivity was improved significantly on going from organic solvent to water. Moreover, a 1,4-addition mechanism has been proposed on the basis of the corresponding experimental details and computational analysis.

QUINOLINE DERIVATIVES AS ANTIBACTERIAL AGENTS

Use of a compound for the manufacture of a medicament for the treatment of a bacterial infection provided that the bacterial infection is other than a Mycobacterial infection, said compound being a compound of formula (Ia) or (Ib) a pharmaceutically acceptable acid or base addition salt thereof, a stereochemically isomeric form thereof, a tautomeric form thereof or a N-oxide form thereof. Several of these compounds are also claimed as such. Further the combination of the above compounds with other antibacterial agents is described

A new, efficient and stereoselective synthesis of tricyclic and tetracyclic compounds by samarium diiodide induced cyclisations of naphthyl-substituted arylketones-an easy access to steroid-like skeletons

In this report, we present the application of samarium diiodide induced cyclisations of naphthyl-substituted ketones towards an easy and stereoselective access to tri- and tetracyclic-functionalised compounds. Typical naphthalene derivatives were studied to investigate the scope and limitations of this novel cyclisation process. The model substrates studied demonstrate that the samarium ketyl cyclisations are essentially restricted to the formation of six-membered rings. The diastereoselectivity of these reactions is strongly influenced by the connection of the alkyl side chain to the naphthalene core. γ-Naphth-1-yl-substituted ketones furnished cyclisation products, such as 17 or 22-26, as single diastereomers, whereas γ-naphth-2-yl-substituted precursors gave mixtures of diastereomers - as demonstrated by the conversion of model compound 10 into tricyclic products 18 a/18 b, or that of cyclohexanone derivative 33 into tetracyclic diastereomers 34 a/34 b. Cyclic ketones as ketyl precursors furnished steroid-like tetracyclic skeletons; however, due to the cis/cis fusion of rings B/C and C/D these products have an "unnatural" bowl-like shape. Several of the cyclisation products have been identified by X-ray analyses, which not only proved the constitutions, but also the relative configurations and the preferred conformations. Steroid analogue 23 was subjected to subsequent transformations, which demonstrate that the styrene-like double bond of such compounds can be used for further structural diversification. First attempts to synthesise related azasteroids by incorporating nitrogen atoms into the ketone moiety are also reported. Thus, pyrrolidine derivatives 44 and 47 as well as piperidine derivatives 50 and 52 were subjected to samarium diiodide induced cyclisations. The expected tetracyclic products 48, 49 a/49 b, 51 and 53 a/53 b were obtained in moderate to good yields. The stereoselectivities observed follow the rules already established for the all-carbon precursors. The resulting products, bearing a nitrogen atom in ring D, are interesting azasteroid analogues with "unnatural" configuration.

Dynamic kinetic resolution of allylic alcohols mediated by ruthenium- and lipase-based catalysts.

An enzyme-metal combo reaction has been developed for the dynamic kinetic resolution of allylic alcohols in which racemic substrates are transformed by a lipase and a ruthenium complex in the presence of an acyl donor to allylic acetates of high optical purity in over 80% yield.