106915-02-0

Basic information

• Product Name: 2,4-Pentanedione, 3-(2-cyclohexen-1-yl)-
• CAS NO: 106915-02-0
• Molecular Formula: C11H16O2
• Molecular Weight: 180.247
• Mol File: 106915-02-0.mol

Chemical Properties

• CAS DataBase Reference: 2,4-Pentanedione, 3-(2-cyclohexen-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pentanedione, 3-(2-cyclohexen-1-yl)-(106915-02-0)
• EPA Substance Registry System: 2,4-Pentanedione, 3-(2-cyclohexen-1-yl)-(106915-02-0)

Safety Data

• Hazardous Substances Data: 106915-02-0(Hazardous Substances Data)

Upstream product

• 822-67-3 Cyclohex-2-enol 
• 5401-62-7 1,2-dibromocyclohexane 
• 123-54-6 acetylacetone 
• 1165952-91-9 cyclohexa-1,3-diene 
• 57981-18-7 N-cyclohex-2-enyl-4-methyl-benzenesulfonamide 
• 13257-81-3 4-trimethylsiloxy-3-penten-2-one 
• 1521-51-3 rac-3-bromocyclohexene 
• 110-83-8 cyclohexene 

Downstream Products

• 136933-87-4 3-cyclohexyl-pentane-2,4-dione 
• 40484-98-8 1-(2-methylbenzofuran-3-yl)ethan-1-one 
• 71041-33-3 1-(2-methyl-4,5,6,7-tetrahydrobenzofuran-3-yl)ethanone 

Relevant articles and documents

Palladium-catalyzed addition of mono- and dicarbonyl compounds to conjugated dienes

An inter molecular, palladium-catalyzed addition of the α-C-H bond of monocarbonyl and 1,3-dicarbonyl compounds to dienes has been developed, and an exploration of the scope of these reactions with a broad range of carbonyl compounds and nitriles was cond

Perchloric acid catalyzed homogeneous and heterogeneous addition of β-dicarbonyl compounds to alcohols and alkenes and investigation of the mechanism

(Figure presented) The direct addition of various β-dicarbonyl compounds to a series of secondary alcohols and alkenes has been achieved using 1 mol % perchloric acid (HClO4) as the catalyst. The HClO 4-catalyzed reactions could be conveniently conducted in commercial solvent and gave moderate to excellent yields. Moreover, the silica gel-supported HClO4 could also catalyze the heterogeneous addition for a series of substrates with similar or even higher yields in comparison with the homogeneous ones. The supported catalyst could be readily recovered and reused for four runs. Furthermore, the mechanism of the HClO4- catalyzed addition of the β-diketone to alcohol was investigated, and an SN1 mechanism was proved unambiguously for the first time through a series of experiments. The discrimination of catalytic abilities among different Bronsted acids was also rationalized by DFT calculations.

Silver Salt-Mediated Allylation Reactions Using Allyl Bromides

A facile, efficient, and chemoselective synthesis of allylic amides has been developed. Allyl bromides were used as the precursors activated by silver triflate. A Ritter-type reaction readily proceeded to give various allyl amides under mild conditions. The reaction protocol was also applicable to different nucleophilic partners to give a wide range of allyl-substituted products in the absence of a base.

Fluorinated alcohols as promoters for the metal-free direct substitution reaction of allylic alcohols with nitrogenated, silylated, and carbon nucleophiles

The direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as reaction media is described. The developed procedure is simple, works under mild conditions (rt, 50 and 70 °C), and proves to be very general, since different nitrogenated nucleophiles and carbon nucleophiles can be used achieving high yields, especially when HFIP is employed as solvent and aromatic allylic alcohols are the substrates. Thus, sulfonamides, carbamates, carboxamides, and amines can be successfully employed as nitrogen-based nucleophiles. Likewise, silylated nucleophiles such as trimethylsilylazide, allyltrimethylsilane, trimethylsilane, and trimethylsilylphenylacetylene give the corresponding allylic substitution products in high yields. Good results for the Friedel-Crafts adducts are also achieved with aromatic compounds (phenol, anisole, indole, and anilines) as nucleophiles. Particularly interesting are the results obtained with electron-rich anilines, which can behave as nitrogenated or carbon nucleophiles depending on their electronic properties and the solvent employed. In addition, 1,3-dicarbonyl compounds (acetylacetone and Meldrum's acid) are also successfully employed as soft carbon nucleophiles. Studies for mechanism elucidation are also reported, pointing toward the existence of carbocationic intermediates and two working reaction pathways for the obtention of the allylic substitution product.

FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

A direct intermolecular addition of nitrogen and 1,3-dicarbonyl nucleophiles to stabilized double bonds (styrenes, 1,3-dienes, enol-ethers, sugars.) in the presence of green and inexpensive FeCl3 catalyst is described.

Selective benzylic and allylic alkylation of protic nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds

The acid-catalyzed benzylic and allylic alkylation of protic nucleophiles is fundamentally important for the formation of carbon-carbon and carbon-heteroatom bonds, and it is a formidable challenge for benzylic and allylic amine derivatives to be used as the alkylating agents. Herein we report a highly efficient benzylic and allylic alkylation of protic carbon and sulfur nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds at room temperature. In the presence of a catalytic amount of inexpensive ZnCl2-TMSCl (TMSCl: chlorotrimethylsilane), 1,3-diketones, β-keto esters, β-keto amides, malononitrile, aromatic compounds, thiols, and thioacetic acid can couple with a broad range of tosylactivated benzylic and allylic amines to give diversely functionalized products in good to excellent yields and with high regioselectivity. Furthermore, the cross-coupling reaction of 1,3-dicarbonyl compounds with benzylic propargylic amine derivatives has been successfully applied to the one-step synthesis of polysubstituted furans and benzofurans.

Microwave-irradiated transition-metal catalysis: Rapid and efficient dehydrative carbon-carbon coupling of alcohols with active methylenes

A rapid and highly productive synthetic microwave-irradiation protocol for transition-metal-catalyzed carbon-carbon coupling of a wide range of benzylic/allylic alcohols with β-diones, β-keto esters, and dialkyl malonates is reported. In a representative

The lewis acidic ruthenium-complex-catalyzed addition of β-diketones to alcohols and styrenes is in fact brensted acid catalyzed

The Perchlorate salt of the dicationic bipy-ruthenium complex cis-[Ru(6,6′-Cl2bipy)2(H2O)2] 2+ effectively catalyzes addition of β-diketones to secondary alcohols and styrenes to yield the α-alkylated β-diketones. In a catalytic addition reaction of acetylacetone to 1-phenylethanol, the κ2-acetylacetonate complex [Ru(6,6′-Cl 2bipy)2(κ2-acac)]ClO4 was isolated after the catalysis; this complex is readily synthesized by reacting cis-[Ru(6,6′-Cl2bipy)2-(H2O) 2] (ClO4)2 with acetylacetone. [Ru(6,6′-Cl2bipy)2(κ-acac)]ClO4 is unreactive toward 1-phenylethanol in the presence of HClO4; it also fails to catalyze the addition of acetylacetone to 1-phenylethanol. On the basis of these observations, it is proposed and confirmed by independent experiments that the catalytic addition of β-diketones to the secondary alcohols is in fact catalyzed by the Bronsted acid HClO4, which is generated by the reaction of cis-[Ru(6,6′-Cl2bipy)2(H 2O)2]-(ClO4)2 with the β-diketone.

Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Bronsted acids

(Chemical Equation Presented) We have developed an environmentally benign synthetic approach to nucleophilic substitution reactions of alcohols that minimizes or eliminates the formation of byproducts, resulting in a highly atom-efficient chemical process. Proton- and metal-exchanged montmorillonites (H- and Mn+-mont) were prepared easily by treating Na +-mont with an aqueous solution of hydrogen chloride or metal salt, respectively. The H-mont possessed outstanding catalytic activity for nucleophilic substitution reactions of a variety of alcohols with anilines, because the unique acidity of the H-mont catalyst effectively prevents the neutralization by the basic anilines. In addition, amides, indoles, 1,3-dicarbonyl compounds, and allylsilane act as nucleophiles for the H-mont-catalyzed substitutions of alcohols, which allowed efficient formation of various C-N and C-C bonds. The solid H-mont was reusable without any appreciable loss in its catalytic activity and selectivity. Especially, an Al3+-mont showed high catalytic activity for the α-benzylation of 1,3-dicarbonyl compounds with primary alcohols due to cooperative catalysis between a protonic acid site and a Lewis acidic Al3+ species in its interlayer spaces.

Catalytic allylic alkylation via the cross-dehydrogenative-coupling reaction between allylic sp3 C-H and methylenic sp3 C-H bonds

A catalytic allylic alkylation was developed via the cross-dehydrogenative-coupling reaction of allylic sp3 C-H and methylenic sp3 C-H catalyzed by copper bromide and cobalt chloride in the presence of an oxidizing reagent, t-BuOOH.