1671-75-6

Usage

Uses

Used in Organic Synthesis:
HEPTANOPHENONE is used as a building block for organic synthesis, contributing to the creation of various complex organic compounds due to its versatile chemical structure.
Used in Chromatography:
HEPTANOPHENONE is used as a test compound for comparing the kinetic performance of monolithic and fused-core capillary C(18) columns in isocratic-elution liquid chromatography, helping to evaluate and improve the efficiency of separation techniques in analytical chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 6229, 1987 DOI: 10.1016/S0040-4039(00)61854-3

Upstream product

• 614-54-0 1-phenylheptan-1-ol 
• 3761-92-0 n-hexylmagnesium bromide 
• 100-47-0 benzonitrile 
• 108-86-1 bromobenzene 
• 2528-61-2 Heptanoic acid chloride 
• 71-43-2 benzene 
• 111-14-8 oenanthic acid 
• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 63035-40-5 1-lithio-1,1-bis(1,3,2-dioxaborin-2-yl)hexane 
• 14374-45-9 1-heptynylbenzene 
• 100-52-7 benzaldehyde 
• 693-02-7 hex-1-yne 
• 27039-14-1 benzoic acid 3-pyridyl ester 

Downstream Products

• 102320-89-8 2-phenyl-1-[2]pyridyl-octan-2-ol 
• 92040-89-6 1-phenyl-heptane-1,2-dione-2-oxime 
• 1078-71-3 heptylbenzene 
• 69060-57-7 hexyl phenyl ketone oxime 
• 100609-87-8 1-(3-nitro-phenyl)-heptan-1-one 
• 23302-84-3 3-hydroxy-3-phenyl-nonanoic acid 
• 66591-15-9 1-phenyl-heptan-1-one-(2,4-dinitro-phenylhydrazone) 
• 854216-37-8 2,2-dimethyl-1-phenyl-heptan-1-one 
• 854216-35-6 2-ethyl-2-methyl-1-phenyl-heptan-1-one 
• 94763-03-8 7-Phenyl-n-tetradecanol-⁽⁷⁾ 
• 167476-86-0 Hexyl-[1-phenyl-hept-(E)-ylidene]-amine 
• 131342-19-3 (R)-1-((S)-Naphthalene-1-sulfinyl)-2-phenyl-octan-2-ol 
• 131342-19-3 (S)-1-((S)-Naphthalene-1-sulfinyl)-2-phenyl-octan-2-ol 
• 106560-96-7 1-phenyl-heptylamine 

Relevant academic research and scientific papers

Catalytic transformation of aldimine to ketimine by Wilkinson's complex through transimination

(equation presented) The C-H bond activation in homogeneous catalysis is important for carbon skeleton construction through C-C bond formation. In this report, a new direct synthesis of ketimine from aldimine bearing no coordination site is demonstrated with high catalytic efficiency. Transimination is the major role for this catalytic reaction.

Direct formation of alkylzinc chlorides using a new active zinc

The reduction of zinc cyanide by lithium napthalenide yields an active form of zinc which undergoes direct oxidative addition to alkylchlorides with the tolerance of some functionality.

Polymeric reagents with propane-1,3-dithiol functions and their precursors for supported organic syntheses

Reliable completely odorless syntheses of soluble copolymeric reagents of styrene type containing propane-1,3-dithiol functions able to convert carbonyl compounds into 1,3-dithiane derivatives and to support other useful transformations are reported together with their progenitor copolymers containing benzenesulfonate or thioacetate groups perfectly stable in open air and suitable for unlimited storage. The effectiveness of the prepared reagents as tools for polymer-supported syntheses to produce ketones by aldehyde umpolung and alkylation is tested in the conversion of benzaldehyde to phenyl n-hexyl ketone starting from copolymers with different contents of active units and molecular weights. To facilitate the adaptation of the prepared soluble copolymeric reagents to other possible applications, a table of solvents and nonsolvents is presented.

Preparation and reactions of new dialkylzincs obtained by a boron-zinc transmetalation

Various aliphatic organoboron derivatives were transmetalated to the corresponding dialkylzincs using diethyl- or dimethyl-zinc. This allows an access to zinc reagents not readily available by standard methods. Didecylzinc obtained by this method adds with good enantioselectivity (83% ee) to PhCHO in the presence of catalytic amounts of (1R, 2R)-1,2-bis-(trifluorosulfonamido)cyclohexane.

Dual functionalities of hydrogen-bonding self-assembled catalysts in chelation-assisted hydroacylation

(Figure Presented) A recyclable catalyst for chelation-assisted hydroacylation of an olefin with primary alcohol was developed using hydrogen-bonding self-assembled catalysts consisting of 2,6-diaminopyridine and barbiturate phosphine - rhodium(I) complex. Upon heating, these two catalysts act as homogeneous catalysts due to cleavage of the hydrogen bond, and these associate to form supramolecular assemblies via hydrogen bonding that can be separated from immiscible product phase upon cooling after the reaction.

Direct conversion of benzyl alcohol to ketone by polymer-supported Rh catalyst

Benzyl alcohol reacted with 1-alkene to give the corresponding ketone by in situ generated polystyrene-based rhodium catalyst. The catalytic activity of this polymer-supported rhodium catalyst has not been reduced after reusing it four times.

A New Solvent System for Recycling Catalysts for Chelation-Assisted Hydroacylation of Olefins with Primary Alcohols

A new method to separate and reuse the catalyst system consisting of a rhodium complex and 2-aminopyridines for chelation-assisted hydroacylation was achieved using phenol and 4,4′-dipyridyl as the reaction medium, and 4-diphenylphosphinobenzoic acid as a ligand. Copyright

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.

Direct conversion of secondary propargyl alcohols into 1,3-di-arylpropanoneviaDBU promoted redox isomerization and palladium assisted chemoselective hydrogenation in a single pot operation

Palladium(ii)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohols to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceedviaredox isomerisation of secondary propargyl alcohols followed by chemoselective reduction of an enone double bond with formic acid as an adequate hydrogen donor. A large number of 1,3-diarylpropanone derivatives may readily be prepared from a milligram to a multigram scale.

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.