58977-36-9

Usage

InChI:InChI=1/C12H16O/c1-2-12(13)10-6-9-11-7-4-3-5-8-11/h3-5,7-8H,2,6,9-10H2,1H3

Upstream product

• 18496-54-3 phenylbutyric acid chloride 
• 79-03-8 propionyl chloride 
• 2687-12-9 cinnamyl chloride 
• 12075-68-2 triethyl aluminum sesquichloride 
• 75-89-8 2,2,2-trifluoroethanol 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 57242-69-0 2,3-dihydro-4H-thiopyran-4-one 
• 42850-68-0 1,4-dioxa-8-thiaspiro[4.5]decane 
• 1462-75-5 3-phenylpropylmagnesium bromide 
• 1821-12-1 4-Phenylbutyric acid 
• 2046-18-6 4-phenylbutyronitrile 
• 925-90-6 ethylmagnesium bromide 
• 90996-77-3 2-benzyl-2-phenylthio-4,4-ethylenedioxythiane 
• 90996-73-9 2-phenylthio-4,4-ethylenedioxythiane 

Downstream Products

• 58249-47-1 1-phenyl-3-cyclopropylpropane 
• 60012-62-6 phenyl-1 hexanol-2 

Relevant academic research and scientific papers

Synthesis of aliphatic ketones from allylic alcohols through consecutive isomerization and chelation-assisted hydroacylation by a rhodium catalyst

Abstract: An allylic alcohol, utilized as a precursor for an aliphatic aldehyde, reacted with olefins to afford aliphatic ketones in the presence of RhCl(PPh3)3, 2-amino-4-picoline, aniline, and benzoic acid through a tandem reaction of an isomerization and a chelation-assisted hydroacylation.

Process for the solid phase synthesis of aldehyde, ketone, oxime, amine, hydroxamic acid and αβ-unsaturated carboxylic acid and aldehyde compounds

This invention is directed to a process for the solid phase synthesis of aldehyde, ketone, oxime, amine, hydroxamic acid and α,β-unsaturated carboxylic acid and aldehyde compounds and to polymeric hydroxylamine resin compounds useful therefor.

Solvolysis of 2,2-dialkylvinyl iodonium salt: Alkyl participation and possibility of a primary vinylic cation intermediate

Solvolysis of (E)- and (Z)-2-methyl-5-phenyl-1-pentenyl(phenyl)iodonium tetrafiuoroborate (1·BF4) was carried out in various alcohols, acetic acid, and aqueous solutions at 60 °C. Products (after acid hydrolysis) include iodobenzene and 2-methyl-5-phenylpentanal as well as rearranged ones: 6- phenyl-2-hexanone, 6-phenyl-3-hexanone, 6-phenyl-2-hexyne, 6-phenyl- 1,2- hexadiene, and 6-phenyl-2,3-hexadiene. The products of α-elimination, including 1-methyl-3-phenyl-1-cyclopentene, were also obtained in methanol and ethanol. Solvolysis of the E isomer (E)-1 is faster than that of (Z)-1 in every solvent examined. The percentage of rearrangement is higher with (E)-1 than with (Z)-1, and the main rearranged products are those of migration of the alkyl group trans to the iodonio group, but migration of the cis alkyl group is also involved. Theoretical calculations suggest that interconversion between the secondary Vinylic cations by 1,2-hydride shift is rapid. These results show that a major heterolysis reaction occurs with β-alkyl participation to directly give a secondary vinylic cation, but stereochemistry of the unrearranged substitution products suggests that formation of the primary vinylic cation is also involved in less nucleophilic solvents like acetic acid and 2,2,2-trifluoroethanol.

Parallel synthesis of aldehydes and ketone facilitated by a new solid- phase Weinreb amide

This paper describes a novel supported Weinreb amide resin that facilitates parallel synthesis of aldehydes and ketones on a scale useful for chemical library synthesis. This new resin makes it possible to produce custom aldehydes and ketones from a wide range of carboxylic acids, including N-BOC-amino acids. A variety of commercially unavailable aldehydes are easily synthesized in parallel and obtained in high purity via a simple filtration workup, thus facilitating parallel synthesis of lead optimization libraries that typically require custom synthesis of aldehyde intermediates for development of structure-activity relationships. To demonstrate the utility of this method, we synthesized a small library based on a supported Horner- Emmons reagent. This is the first time it has been shown that aldehydes generated via a supported Weinreb amide could be used directly as reagents in chemical library synthesis employing moisture-sensitive reactions. The analogous solution reaction is not suited for parallel synthesis because of the laborious extractive workup procedure necessary and, at times, the instability of these reactive intermediates.

Solvolysis of β,β-dialkylvinyliodonium salt: Primary vinyl cation intermediate and alkyl participation

Solvolysis of both E and Z isomers of a β,β-dialkylvinyl-(phenyl)iodonium salt gave extensively rearranged products. A mechanism involving a primary vinyl cation intermediate as well as the alkyl participation leading to secondary vinyl cations is proposed.

A New C-C Bond-forming Free Radical Rearrangement

On treatment with tributyltin hydride and azoisobutyronitrile in benzene at reflux α-aryl-β-bromoalkyl vinyl ethers rearrange in moderate yield to δ-aryl ketones: possible mechanistic rationales are discussed for this novel C-C bond-forming process.

Substituted Thian-4-ones. Part 3. Synthesis and Reactions of 2-Alkyl-5,6-Dihydrothiin-4-ones

A number of approaches to the synthesis of 2-alkyl-5,6-dihydrothiin-4-ones (1) are described.The treatment of 2-butylthian-4-one (3) with N-chlorosuccinimide gave a mixture of the alkenes (1a) and (4) and the corresponding reaction with the dioxolane (5) also proved to be non-regioselective. 2-Chlorodihydrothiin-4-one (6) was prepared and its reactions with a number of butylcoper reagents studied.The only product isolated from these reactions was 2,2-dibutylthian-4-one (12). 3-Chlorodihydrothiin-4-one (8) was successfully prepared and converted into 2-butyl-3-chlorothian-4-one (13) but dehydrohalogenation could not be achieved.A successful synthesis of the title compounds was achieved based on the generation and alkylation of the β-acylvinyl anion equivalent (14).Attempts to desulphurise 2-benzyl-5,6-dihydrothiin-4-one (1d) and related compounds in order to produce the α,β-unsaturated ketone (18) are discussed.

PREPARATION AND SYNTHTETIC UTILITY OF CYCLOPROPYL PHENYL SULFIDES

Primary alkyl halides and epoxides react with 1-lithiocyclopropyl phenyl sulfide to give derivatives suitable for transformation to carbonyl compounds or for desulfurization.

Quaternary ammonium antiarrhythmic drugs

Quaternary ammonium salts of certain phenylbutylamines are useful antiarrhythmic drugs. A method for treating arrhythmia and prolonging the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such quaternary ammonium salts are disclosed.

A CONVENIENT METHOD FOR THE DIRECT PREPARATION OF KETONES FROM 2-(6-(2-METHOXYETHYL)PYRIDYL) CARBOXYLATES AND ALKYL IODIDES BY USE OF ZINC DUST AND A CATALYTIC AMOUNT OF NICKEL DICHLORIDE

Treatment of 2-(6-(2-methoxyethyl)pyridyl) carboxylates with alkyl iodides in the presence of zinc dust and a catalytic amount of NiCl2 in DMF at 50 deg C affords unsymmetrical ketones in good yields by a one-pot procedure.