1220079-34-4

Basic information

• Product Name: (1R,3aS,5S,6aS)-1-benzyl-5-hydroxy-hexahydropentalen-2(1H)-one
• CAS NO: 1220079-34-4
• Molecular Weight: 230.307
• Mol File: 1220079-34-4.mol

Chemical Properties

• CAS DataBase Reference: (1R,3aS,5S,6aS)-1-benzyl-5-hydroxy-hexahydropentalen-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3aS,5S,6aS)-1-benzyl-5-hydroxy-hexahydropentalen-2(1H)-one(1220079-34-4)
• EPA Substance Registry System: (1R,3aS,5S,6aS)-1-benzyl-5-hydroxy-hexahydropentalen-2(1H)-one(1220079-34-4)

Safety Data

• Hazardous Substances Data: 1220079-34-4(Hazardous Substances Data)

Upstream product

• 1220079-26-4 (1R,3aS,5S,6aS)-1-benzyl-5-(tert-butyldimethylsilyloxy)-hexahydropentalen-2(1H)-one 

Relevant articles and documents

Synthesis of functionalized hydropentalenes by an asymmetric deprotonation/alkylation strategy

The functionalization of differently substituted hydropentalenone derivatives 9, derived from the Weiss diketone (8) by enantioselective deprotonation in the presence of lithium (R,R)-bis(1-phenylethyl)amide/LiCl (11-LiCl) as the chiral base is described. In the first route the resulting enolate was treated, directly with alkyl halides as electrophiles to give the target a-alkylhydropentalenones 12, whereas in the second route the enolate was trapped as one of the triethylsilyl enol ethers 17, from which the enolate was regenerated, by treatment with MeLi prior to alkylation with alkyl halides. The substituents on 9 seemed to influence which strategy is favored: for the OTBS-substituted hydropentalenone 9a the direct deprotonation/alkylation is preferred, whereas for the acetal-substituted hydropentalenone 9b the silyl enol ether route is more suitable. In all cases the α-alkylated hydropentalenones 12 and 15 were isolated with good diastereoselectivities.