31929-07-4

Usage

Type of compound

Synthetic chemical compound

Usage

Synthesis of pharmaceuticals and organic compounds

Chemical structure

Alpha, beta-unsaturated cyclic ketone

Physical state

Yellowish liquid

Odor

Fruity, hoppy

Application

Flavoring agent in food and beverage industry

Potential applications

Medicine, precursor in organic synthesis

Safety precautions

Causes skin, eye, and respiratory irritation; harmful if ingested or inhaled

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 106-95-6 allyl bromide 
• 221165-85-1 2-(2-iodo-allyl)-2-methyl-cyclohexane-1,3-dione 
• 107-18-6 allyl alcohol 
• 147973-93-1 (Z)-2-(3-iodo-2-propenyl)-2-methyl-1,3-cyclohexanedione 
• 100-44-7 benzyl chloride 
• 31929-06-3 3-Allyloxy-2-methyl-2-cyclohexen-1-on 
• 504-02-9 1,3-cylohexanedione 

Downstream Products

• 148110-99-0 3-(1-Methyl-but-3-enyl)-cyclohex-2-enone 
• 90105-51-4 3-Hydroxy-2-methyl-2-(2-propenyl)cyclohexan-1-one 
• 552855-48-8 (1-methyl-2,6-dioxo-cyclohexyl)-acetaldehyde 
• 911213-97-3 2-(3-azidopropyl)-2-methyl-1,3-cyclohexanedione 
• 1393100-39-4 C₁₈H₂₀O₃S 
• 1393100-41-8 C₁₅H₂₂O₃S 
• 90130-88-4 (2R,3S)-3-hydroxy-2-methyl-2-propylcyclohexanone 
• 674347-42-3 (1S,3aS,7aS)-7a-Hydroxy-3a-methyl-4-oxo-octahydro-indene-1-carbaldehyde 
• 674347-42-3 (1R,3aS,7aS)-7a-Hydroxy-3a-methyl-4-oxo-octahydro-indene-1-carbaldehyde 
• 674347-67-2 2-(3-formylpropyl)-2-methyl-1,3-cyclohexanedione 

Relevant academic research and scientific papers

Asymmetric construction of novel bicyclo[4.4.0] and [4.3.0]ring systems via intramolecular Horner-Wadsworth-Emmons reactions

Novel perhydro-indanones and -naphthalenones having a quaternary stereogenic carbon and tetrasubstituted olefinic linkage were prepared via asymmetric intramolecular Horner-Wadsworth-Emmons reactions. The optically active binaphthyl phosphonates were conn

Desymmetric enantioselective reduction of cyclic 1,3-diketones catalyzed by a recyclable p-chiral phosphinamide organocatalyst

The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that the P-stereogenic phosphinamides are powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol displays a broad substrate scope that is amenable to a series of cyclic 2,2-disubstituted five- and six-membered 1,3-diketones. The chiral cyclic 3-hydroxy ketone products bearing an all-carbon chiral quaternary center could be obtained with high enantioselectivities (up to 98% ee) and diastereoselectivities (up to 99:1 dr). Most importantly, the reactions could be practically performed on the gram scale and the catalysts could be reused without compromising the catalytic efficiency. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species. The results disclosed herein bode well for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

Convenient preparation of synthetically useful chiral quaternary carbon-containing bicyclic compounds with organocatalysts

Chiral quaternary carbon-containing bicyclic compounds possessing carbonyl functionalities were efficiently synthesized through asymmetric intramolecular aldol reactions with organocatalysts. Bicyclo [3.3.0] and [3.4.0] systems were constructed with a dia

Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts

We have developed biocatalytic methods for the stereoselective reduction of cyclic prochiral 1,3-diketones for the production of optically active β-hydroxyketones and/or 1,3-diols. The recombinant ketoreductase KRED1-Pglu (formulated as purified catalyst)

Asymmetric Synthesis of a Bicyclo[43.0]nonene Derivative Bearing a Quaternary Carbon Stereocenter: Desymmetrization of σ-Symmetrical Diketones through Intramolecular Addition of an Alkenyl Anion

The enantioselective synthesis of a bicyclo[4.3.0]nonene derivative bearing a quaternary carbon stereocenter is achieved by employing a desymmetrization strategy involving an intramolecular addition. The intramolecular nucleophilic addition of a highly reactive carbanion generated from an alkenyl iodide in the presence of a chiral ligand occurs with discrimination of two keto carbonyl groups to give the corresponding bicyclic compound in 81% yield and 39% ee. Asymmetric synthesis via an intramolecular desymmetrization strategy using a chiral ligand-carbanion complex represents a complementary approach to using chiral organocatalysts or chiral ligand-transition-metal complexes.

Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones

A single-pot Cu-catalyzed enantio- and diastereoselective tandem hydroboration/borylative cyclization of alkynes with ketones for the synthesis of carbocycles is reported. The reaction proceeds via desymmetrization and generates four contiguous stereocent

Silica Support-Enhanced Pd-Catalyzed Allylation Using Allylic Alcohols

Although allylation using allylic alcohol is an environmentally-friendly method because of water being the sole byproduct in such reactions, allylic alcohol is one of the most difficult allylating agents in Pd-catalyzed allylation of nucleophiles. In this study, we successfully developed a mesoporous silica-supported Pd complex as an efficient catalyst for the allylation of nucleophiles using allylic alcohols as allylating agents. The allylic alcohol is activated by the silanol group on the support surface, which easily undergoes a π-allylpalladium intermediate formation. The catalytic activity of the supported Pd complex was ca. 9 times higher than that of its homogeneous precursor Pd complex. A highest turnover number of 4500 based on Pd was achieved. Various nucleophiles and allylic alcohol derivatives could be used as substrates. Not only the detailed catalyst structure but also the reaction mechanism including the concerted activation of allylic alcohol by the Pd complex and silanol were investigated by several spectroscopic techniques, such as Pd K-edge XAFS, solid-state NMR, and in-situ FT-IR measurements.

Method of manufacturing compds. Allylnaphthol

PROBLEM TO BE SOLVED: To provide a production method of an allyl compound of carrying out the dehydration allylation of a substrate having S, C or N which is a nucleophilic atom, especially S under the presence of a catalyst system consisting of a catalyst precursor having a specific structure and a specific ligand. SOLUTION: The production method of allyl compounds comprises as follow. A catalyst precursor chosen from Formula (1) and Formula (2) and a ligand are mixed, or a catalyst precursor, an allyl alcohol, and a ligand are mixed, then allyl alcohols and a substrate are blended and made to react. The ligand is quinaldic acid or picolinic acid, and the substrate is thiols, thiocarboxylic acids or the like. [Ru(C5H5)(CH3CN)3]PF6(1). [Ru[C5(CH3)5](CH3CN)3]PF6(2). COPYRIGHT: (C)2012,JPOandINPIT

An easy route toward enantio-enriched polycyclic derivatives via an asymmetric domino conjugate reduction-aldol cyclization catalyzed by a chiral Cu(I) complex

A highly efficient reductive-aldol cyclization mediated by a chiral Cu(I) complex and an organosilane yielded to cyclic or polycyclic derivatives. An excellent control of the selectivities was reached in most cases (dr up to 100:0 and ee up to 95%). After

A synthetic approach to terpendoles: Decahydrobenzo[f]chromenes by an intermolecular Diels-Alder route

Synthesis of decahydro-1H-benzo[f]chromene system using intermolecular Diels-Alder reaction has been carried out for the construction of skeleton of terpendole class of terpenoids. ARKAT-USA, Inc.