22789-80-6

Basic information

• Product Name: 2(1H)-Naphthalenone, 3,4,4a,5,6,7-hexahydro-4a-methyl-
• CAS NO: 22789-80-6
• Molecular Formula: C11H16O
• Molecular Weight: 164.247
• Mol File: 22789-80-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2(1H)-Naphthalenone, 3,4,4a,5,6,7-hexahydro-4a-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Naphthalenone, 3,4,4a,5,6,7-hexahydro-4a-methyl-(22789-80-6)
• EPA Substance Registry System: 2(1H)-Naphthalenone, 3,4,4a,5,6,7-hexahydro-4a-methyl-(22789-80-6)

Safety Data

• Hazardous Substances Data: 22789-80-6(Hazardous Substances Data)

Upstream product

• 826-56-2 4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 90496-76-7 C₉H₈NO^(1-)*Li⁽¹⁺⁾ 

Downstream Products

• 313478-13-6 2-(1',2-epoxyethyl-1'-phenylsulfoxy)-4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene 
• 31654-83-8 (+/-)-cis-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-ol 

Relevant articles and documents

REACTIVITE DE LITHIENS DERIVES D'ETHERS DE LA CYANHYDRINE DU BENZALDEHYDE VIS-A-VIS D'α-ENONES CYCLIQUES

Conjugate addition of reagent 1A to 2-cyclohexenone 3 can be realized in THF-HMPT, so that one-pot conjugate addition - CH3I enolate trapping, leading to trans 2-methyl 3-benzoylcyclohexanone 17 can be easily performed.From isophorone 4 and Δ1(9)-2-octalone 5, 1,4-addition under kinetic control is observed in THF.In the presence of HMPA, the reaction is under thermodynamic control.At low temperatures enolate 19a is in equilibrium with 1A and 4; from 4 at 0 deg C or 5 at -65 deg C or at 0 deg C, the equilibrium lies on the side of starting materials.No reaction between 1A and 6 takes place in any solvent.The reaction of 1B and isophorone 4 in THF leads to 1,2-addition under kinetic control and to 1,4-addition under thermodynamic control.In THF-HMPT, retro-Michael addition is observed.However, 1,2-addition takes place in THF to 6. The different results are interpreted in terms of interplay of ion-pairing, steric decompression and steric hindrance to 1,4-addition as well as the possibility of participation of the Li cation for 1,2-addition.