59145-20-9

Basic information

• Product Name: 2-Cinnamoyl-5,5-dimethyl-cyclohexan-1,3-dion
• Synonyms: 2-Cinnamoyl-5,5-dimethyl-cyclohexan-1,3-dion
• CAS NO: 59145-20-9
• Molecular Weight: 270.328
• Mol File: 59145-20-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Cinnamoyl-5,5-dimethyl-cyclohexan-1,3-dion(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cinnamoyl-5,5-dimethyl-cyclohexan-1,3-dion(59145-20-9)
• EPA Substance Registry System: 2-Cinnamoyl-5,5-dimethyl-cyclohexan-1,3-dion(59145-20-9)

Safety Data

• Hazardous Substances Data: 59145-20-9(Hazardous Substances Data)

Upstream product

• 111-49-9 hexamethylene imine 
• 1755-15-3 2-acetyldimedone 
• 100-52-7 benzaldehyde 

Downstream Products

• 59145-21-0 5,5-dimethyl-2-(3-phenyl-propionyl)-cyclohexane-1,3-dione 
• 1308887-14-0 3-(3,4-dimethylphenylamino)-5,5-dimethyl-2-[(E)-3-phenylprop-2-enoyl]cyclohex-2-en-1-one 
• 1308887-15-1 3-(4-methoxyphenylamino)-5,5-dimethyl-2-[(E)-3-phenylprop-2-enoyl]cyclohex-2-en-1-one 
• 663938-04-3 1-(4-methoxyphenyl)-7,7-dimethyl-2-phenyl-1,2,3,4,5,6,7,8-octahydroquinoline-4,5-dione 
• 1308887-30-0 1-(3,4-dimethylphenyl)-7,7-dimethyl-2-phenyl-1,2,3,4,5,6,7,8-octahydroquinoline-4,5-dione 
• 1308887-07-1 2-[(E)-1-(4-methoxybenzylamino)-3-phenylprop-2-en-1-ylidene]-5,5-dimethylcyclohexane-1,3-dione 

Relevant articles and documents

Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones

We have shown that reaction of nitromethane with cinnamoyl derivatives of five- and six-membered carbo- and heterocylic β-dicarbonyl compounds in the presence of 1,1,3,3-tetramethylguanidine proceeds according to the mechanism of 1,4-conjugate addition to the enone fragment of cinnamoyl moiety to give 2(3)-(3-aryl-4-nitrobutanoyl)-substituted cyclic 1,3- or 2,4-diones in good to excellent yields. Chemoselective reduction of nitro function of the latter leads to synthetically useful and biologically interesting 2(3)-(4-arylpyrrolidin-2-ylidene) derivatives.

Synthesis of exo- and endocyclic enamino derivatives of 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones

Condensation of 2-acetylcyclohexane-1,3-diones with aromatic aldehydes in the presence of piperidine, pyrrolidine, hexamethyleneimine, or morpholine gave the corresponding 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones as the major products and 2-[3-aryl-1-cycloalkylaminoprop-2-en-1-ylidene]cyclohexane-1,3- diones as minor ones. Endocyclic enamino derivatives were synthesized in two steps through enol methyl ethers which reacted with amines. Endocyclic enamino derivatives of 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones containing an aryl group on the nitrogen atom readily underwent cyclization to 1,2,3,4,5,6,7,8- octahydroquinoline-4,5-dione derivatives.