129215-01-6

Basic information

• Product Name: Cyclohexanone, 3-ethenyl-4-(1-methylethyl)-, (3S-trans)- (9CI)
• Synonyms: Cyclohexanone, 3-ethenyl-4-(1-methylethyl)-, (3S-trans)- (9CI)
• CAS NO: 129215-01-6
• Molecular Formula: C11H18O
• Molecular Weight: 166.26002
• Product Categories: ISOPROPYL
• Mol File: 129215-01-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexanone, 3-ethenyl-4-(1-methylethyl)-, (3S-trans)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 3-ethenyl-4-(1-methylethyl)-, (3S-trans)- (9CI)(129215-01-6)
• EPA Substance Registry System: Cyclohexanone, 3-ethenyl-4-(1-methylethyl)-, (3S-trans)- (9CI)(129215-01-6)

Safety Data

• Hazardous Substances Data: 129215-01-6(Hazardous Substances Data)

Upstream product

• 100295-52-1 (S)-(-)-4-isopropylcyclohex-2-enone 
• 1826-67-1 vinyl magnesium bromide 
• 75-77-4 chloro-trimethyl-silane 

Relevant articles and documents

67. On the Absolute Configuration of Penlanfuran and Related Sesquiterpenoids of the Sponge Dysidea fragilis from the North-Brittany Sea

The 1,4-addition of vinylmagnesium bromide/CuBr*SMe2 to (+)-(4S)-cryptone ((+)-6) in THF in the presence of Me3SiCl gives the silyl enol ether 7 which partly undergoes hydrolysis to ketone 8 on aqueous workup; residual 7 is hydrolyzed with pyridinium p-toluenesulfonate (Py*TsOH) to give 8 which is protected in situ with ethylene glycol and then ozonolized to give aldehyde (-)-10.The latter, on addition of 3-lithiofuran followed by dehydration and deprotection with Py*TsOH, gives the unnatural (4S)-enantiomer (+)-2 of noroxopenlanfuran.All processes, except 11 -> (+)-2, are of good yield.On the basis of previous chemical transformations, this also establishes the (4R)-configuration for penlanfuran ((-)-1) and other sesquiterpenoids of the sponge Dysidea fragilis from the North-Britanny sea.Non viable routes to (+/-)-noroxopenlanfuran ((+/-)-2) are also discussed.