13747-73-4

Basic information

• Product Name: 2-(1-Methylethylidene)cyclohexanone
• Synonyms: 2-(1-Methylethylidene)cyclohexanone;2-Isopropylidenecyclohexanone;2-(1-Methylethylidene)-1-cyclohexanone
• CAS NO: 13747-73-4
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.2069
• Mol File: 13747-73-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 120-125℃ (20 Torr)
• Flash Point: 84.4°C
• Appearance: /
• Density: 0.954g/cm³
• Vapor Pressure: 0.124mmHg at 25°C
• Refractive Index: 1.4922 (589.3 nm)
• CAS DataBase Reference: 2-(1-Methylethylidene)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-Methylethylidene)cyclohexanone(13747-73-4)
• EPA Substance Registry System: 2-(1-Methylethylidene)cyclohexanone(13747-73-4)

Safety Data

• Hazardous Substances Data: 13747-73-4(Hazardous Substances Data)

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

• 100-64-1 cyclohexanone-oxime 
• 67-64-1 acetone 
• 92735-08-5 3-trimethylsiloxycyclohexene 
• 108-94-1 cyclohexanone 
• 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 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 90646-70-1 7-methyl-6-octenoic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 94417-55-7 2-(1-Methyl-1-methylselanyl-ethyl)-cyclohexanone 
• 5212-77-1 2,2-dimethyl-cycloheptanone oxime 
• 3304-23-2 2-(1'-hydroxy-1-methylethyl)cyclohexanone 

Downstream Products

• 125158-91-0 1-Allyl-2-isopropylidene-cyclohexanol 
• 108685-85-4 6-chloro-2-isopropylidenecyclohexanone 
• 13954-15-9 2-<2-Chlor-propyl-(2)>-2-methyl-cyclohexanon 
• 1422007-81-5 2-[1-(5-bromo-1-methyl-1H-indol-3-yl)-1-methylethyl]cyclohexanone 
• 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 
• 13747-75-6 2-isopropenyl-2-methyl-cyclohexanone 
• 1004-77-9 2-isopropylcyclohexanone 
• 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 
• 106432-06-8 2-Isopropylidene-1-methyl-cyclohexanol 
• 119011-80-2 (2Z,4E)-3-methyl-4-(2-isopropylidenecyclohexylidene)but-2-enoic acid 

Relevant articles and documents

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.

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

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.