224967-43-5

Basic information

• Product Name: 2-Cyclohexen-1-one,2,3-dimethyl-5-(1-methylethyl)-,(5R)-(9CI)
• Synonyms: 2-Cyclohexen-1-one,2,3-dimethyl-5-(1-methylethyl)-,(5R)-(9CI)
• CAS NO: 224967-43-5
• Molecular Formula: C11H18O
• Molecular Weight: 0
• Product Categories: ISOPROPYL
• Mol File: 224967-43-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Cyclohexen-1-one,2,3-dimethyl-5-(1-methylethyl)-,(5R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one,2,3-dimethyl-5-(1-methylethyl)-,(5R)-(9CI)(224967-43-5)
• EPA Substance Registry System: 2-Cyclohexen-1-one,2,3-dimethyl-5-(1-methylethyl)-,(5R)-(9CI)(224967-43-5)

Safety Data

• Hazardous Substances Data: 224967-43-5(Hazardous Substances Data)

Upstream product

• 224967-18-4 (2S,3S,5S)-2-methyl-3-(tert-butyldimethylsiloxy)-5-(2-propyl)cyclohexanone 
• 499-71-8 carvotanacetone 
• 224967-39-9 (1RS,5S)-1-hydroxy-1,2-dimethyl-5-(2-propyl)-2-cyclohexene 
• 1072085-41-6 (R)-5-Isopropyl-1,2-dimethyl-cyclohex-2-enol 
• 99-49-0 Carvone 
• 75-16-1 methylmagnesium bromide 

Relevant articles and documents

Silver(I)-catalyzed ring-contractive rearrangement: A new entry to 5-alkylidene-2-cyclopentenones

A novel silver(I)-catalyzed ring-contractive rearrangement of 5-substituted 6-diazo-2-cyclohexenones has been developed, providing a new and efficient access to 5-alkylidene-2-cyclopentenones. The AgOTf-catalyzed reaction proceeds through metal-carbenoid formation followed by endocyclic allyl [1,2] migration with excellent stereoselectivity and broad substrate scope.

Synthesis of optically active 5-(tert-butyldimethylsiloxy)-2- cyclohexenone and its 6-substituted derivatives as useful chiral building blocks for the synthesis of cyclohexane rings. Synthesis of carvone, penienone, and penihydrone

Optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone (1) and its 6-substituted derivatives 2a,b were synthesized from the readily available optically active ethyl 3-(tert-butyldimethylsiloxy)-5-hexenoate (4), where the Ti(II)-mediated intramolecular nucleophilic acyl substitution reaction and the FeCl3-mediated ring expansion reaction of a 1- hydroxybicyclo[3.1.0]hexane are the key reactions. The enone 1 reacted with higher-order cyanocuprates with excellent diastereoselectivity to afford the trans-addition products, trans-13, in excellent yields. The reaction of 1 with lower-order cyanocuprates proceeded with moderate to excellent syn- selectivity to afford cis-13. Treatment of trans- and cis-13 with DBU (1,8- diazabicyclo[5.4.0]undec-7-ene) or catalyst p-TSA (p-toluenesulfonic acid) resulted in a β-elimination reaction to furnish the corresponding optically active 5-substituted-2-cyclohexenones 14. The 1,4-addition reaction of 2a and 2b with organocy-anocuprates followed by treatment of the resulting 20 with DBU provided the 2,5-disubstituted-2-cyclohexenones 19 with excellent ee. The conversion of 14 into the 3,5-disubstituted-2-cyclohexenone 22 has also been carried out via 1,2-addition of alkyllithium onto the carbonyl group and the following oxidation with PCC (pyridinium chlorochromate). Similarly, the conversion of 19 into 2,3,5-trisubstituted-2-cyclohexenones 24 has been carried out. A highly efficient, first total synthesis of penienone 25 and penihydrone 26 has been accomplished. Thus, the 1,4-addition reaction of 1 with the (E,E)-1,3-heptadienyl cyanocuprate and consecutive trap of the resulting copper enolate with formaldehyde gave 28, which upon treatment with DBU or Pyr · HF yielded 25 and 26, respectively. An efficient synthesis of both enantiomers of carvone starting from (S)-20ab has been also accomplished.