13747-73-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 4679, 1985 DOI: 10.1021/ja00302a014The Journal of Organic Chemistry, 41, p. 439, 1976 DOI: 10.1021/jo00865a005

InChI:InChI=1/C9H14O/c1-7(2)8-5-3-4-6-9(8)10/h3-6H2,1-2H3

Upstream product

• 13839-78-6 2-(1,4-dioxa-spiro[4.5]dec-6-yl)-propan-2-ol 
• 3304-23-2 2-(1'-hydroxy-1-methylethyl)cyclohexanone 
• 100-64-1 cyclohexanone-oxime 
• 67-64-1 acetone 
• 94417-55-7 2-(1-Methyl-1-methylselanyl-ethyl)-cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 77-76-9 2,2-dimethoxy-propane 
• 108-94-1 cyclohexanone 
• 90646-70-1 7-methyl-6-octenoic acid 
• 78-84-2 isobutyraldehyde 
• 54353-82-1 2-(1,2-epoxy-cyclohexyl)-2-methyl-propionitrile 
• 130739-14-9 1-(2'-hydroxycyclohexyl)-1-methyl-1-phenylsulphonylethane 
• 286-20-4 cyclohexane-1,2-epoxide 
• 92735-08-5 3-trimethylsiloxycyclohexene 

Downstream Products

• 13747-75-6 2-isopropenyl-2-methyl-cyclohexanone 
• 119011-88-0 2-<(ethoxycarbonyl)methyl>-3,4,5,6,7,8-hexahydro-4,4-dimethyl-2H-1-benzopyran 
• 119011-87-9 ethyl 5,5-dimethyl-5-(2-oxocyclohexyl)pent-2-enoate 
• 119011-80-2 (2Z,4E)-3-methyl-4-(2-isopropylidenecyclohexylidene)but-2-enoic acid 
• 106432-06-8 2-Isopropylidene-1-methyl-cyclohexanol 
• 1004-77-9 2-isopropylcyclohexanone 
• 108685-85-4 6-chloro-2-isopropylidenecyclohexanone 
• 1422007-81-5 2-[1-(5-bromo-1-methyl-1H-indol-3-yl)-1-methylethyl]cyclohexanone 
• 13954-15-9 2-<2-Chlor-propyl-(2)>-2-methyl-cyclohexanon 
• 125158-91-0 1-Allyl-2-isopropylidene-cyclohexanol 
• 13747-74-5 α-isopropylidenecyclohexanone 2,4-dinitrophenylhydrazone 
• 82511-88-4 1-(1-Isopropenyl-2-oxo-cyclohexyl)-4-phenyl-[1,2,4]triazolidine-3,5-dione 

Relevant academic research and scientific papers

Catalytic reactions of metalloporphyrins. II. Activation and catalytic aldol condensation of ketone with rhodium(III)-porphyrin perchlorate under neutral and mild conditions

Acetone and methyl ethyl ketone undergo facile and direct metalation at the methyl groups by a cationic (octaethylporphyrinato) rhodium(III) complex with a non-coordinating perchlorate counteranion, (OEP)RhIII(ClO4), under mild conditions.Acetylacetone and ethyl acetoacetate are similarly metalated at the internal methylene groups.The metalation of acetone is first-order with respect to both rhodium complex and ketone, and involves the (OEP)RhIII(ClO4)-assisted, rate-determining enolization of the ketone.The resulting 2-oxopropyl-rhodium derivative undergoes facile cleavage of the C-Rh bond with electrophiles such as H(1+) and Br2.When cyclohexanone is used as substrate, on the other hand, (OEP)RhIII(ClO4) catalyzes the aldol condensation of the ketone effectively, where the intermediate cyclohexanone enolate reacts with the ketone or other carbonyl compound present and regenerates the RhIII complex.An essential aspect of the present reaction is the remarkable ability of (OEP)RhIII(ClO4) to promote enolization of simple ketones by activation with charge-separated III>+ (a Lewis acid) under mild and neutral conditions.The second-order rate constant of (OEP)RhIII(ClO4)-assisted enolization of acetone at 30 deg C (k2 = 2.6 * E-4 M-1 sec-1) is E7 times as large as that of its spontaneous enolization in water, where water is both acid and base.

A catalytic, mild and efficient protocol for the C-3 aerial hydroxylation of oxindoles

A mild, high yielding approach to C-3 hydroxylated oxindoles using catalytic quantities of tetrabutylammonium fluoride and air as the stoicheiometric oxidant is reported over a wide range of substitution patterns.

Platinum-catalyzed cyclization/[1,2]-alkyl migration/allyl shift/cyclization cascade of epoxy alkynyl allyl ethers: A step-economical route to spirobenzo[h]chromanones

In tandem: A PtI4-catalyzed tandem reaction of epoxy alkynyl allyl ethers involving a cyclization, [1,2]-alkyl migration, O→C allyl shift, aromatic cyclization sequence has been achieved to synthesize spirobenzo[h]chromanones. The reaction simultaneously forms two adjacent stereocenters, one of which is a quaternary carbon atom (see scheme). Copyright

An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3·7H2O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone

2-Alkylidenecycloalkanones are powerful synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective β-elimination reaction to (E)-2-alkylidenecycloalkanones in 2-(1-hydroxyalkyl)cycloalkanones. The synthetic value of the present procedure is demonstrated by the synthesis of monoterpene (S)-(-)-pulegone (8) in its optically active form.

One pot synthesis of α,β-unsaturated ketones from the Mukaiyama aldol condensation

Satisfactory yields of α,β-unsaturated ketones are obtained from two trimethylsilylenol ethers and a variety of aldehydes and ketones in a one pot modified Mukaiyama aldol procedure using triethylamine and trifluoroacetic anhydride.

Preparation of α,β-unsaturated carbonyl compounds

A process for the preparation of α,β-unsaturated carbonyl compounds of the formula I STR1 where R1 is hydrogen, C1 -C10 -alkyl, C1 -C10 -alkoxy or aryloxy, R2 is aryl which is unsubstituted or substituted by C1 -C4 -alkyl, C1 -C4 -alkoxy, trifluoromethyl and/or halogen and R3 is tetrahydrofuranyl or aryl which is substituted by C1 -C4 -alkyl, C1 -C4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II STR2 where R1 and R2 have the abovementioned meanings, and R4 and R5 are, independently of one another, hydrogen, C1 -C10 -alkyl or aryl, with a magnesium halide of the formula III where Y is halogen, at from -20° to 100° C., and novel α,β-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.

Lewis Acid - Mediated Addition of Lithiated Alkyl Phenyl Sulphones and Oxiranes. A Method for Synthesis of α,β-Unsaturated Ketones

Efficiency of the reaction of lithiated alkyl aryl sulphones (1-4) with oxiranes (5, 6) is increased by the presence of BF3 or CeCl3.The respective adducts (7-14) were transformed into α,β-unsaturated ketones (15-22) with high yields.

SELENIUM STABILIZED CARBENIUM IONS. LEWIS ACID MEDIATED SELENO-ALKYLATION OF KETONES

Silyl enol ethers of ketones can be successfully selenoalkylated by Lewis acid activated seleno-ketals; the product β-seleno-ketones undergo interesting oxidation-deselenation reactions.

CHEMISTRY OF ENOL ETHERS. LXVIII. SILYL ENOL ETHERS IN A MODIFIED ALDOL-CROTONIC CONDENSATION. PRODUCTION OF α,β-UNSATURATED KETONES

By the condensation of the acetals of acetaldehyde, butyraldehyde, isobutyraldehyde, and acetone with the trimethylsilyl ethers of the enolic forms of cyclohexanone, cyclopentanone, and acetone in the presence of zinc chloride as catalyst and subsequent treatment of the reaction products with dilute hydrochloric acid the following α,β-unsaturated ketones were obtained: Ethylidene-, butylidene-, and isobutylidenecyclohexanones, the corresponding cyclopentanones, and methyl propenyl ketone.

SCOPE AND STEREOCHEMICAL COURSE OF THE (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION

A new, regiospecific annulation approach to highly substituted 5-membered carbocycles has been developed.The "TMS-cyclopentene annulation" involves the reaction of (trimethylsilyl)allenes with electrondeficient alkenes and alkynes in the presence of titanium tetrachloride to afford, in a single step, a functionalized and highly substituted TMS-cyclopentene derivative.Annulations employing α, β-unsaturated ketones proceed stereoselectively via suprafacial addition to the enone.Some useful transformations of the annulation products are also described; for example, treatment with K2CO3-methanol or HF in acetonitrile effects isomerization and desilylation yielding α, β-unsaturated ketones.