222738-51-4

Basic information

• Product Name: 4-n-butyl-8-tert-butyldiphenylsilyloxy-4-hydroxy-3-methyl-1(4H)-naphthalenone
• CAS NO: 222738-51-4
• Molecular Weight: 484.711
• Mol File: 222738-51-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-n-butyl-8-tert-butyldiphenylsilyloxy-4-hydroxy-3-methyl-1(4H)-naphthalenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-n-butyl-8-tert-butyldiphenylsilyloxy-4-hydroxy-3-methyl-1(4H)-naphthalenone(222738-51-4)
• EPA Substance Registry System: 4-n-butyl-8-tert-butyldiphenylsilyloxy-4-hydroxy-3-methyl-1(4H)-naphthalenone(222738-51-4)

Safety Data

• Hazardous Substances Data: 222738-51-4(Hazardous Substances Data)

Upstream product

• 109-72-8 n-butyllithium 
• 222738-47-8 5-tert-butyldiphenylsilyloxy-2-methyl-1,4-naphthoquinone 
• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Relevant articles and documents

Total synthesis of (±)-plumbazeylanone, a naphthoquinone trimer from Plumbago zeylanica

We have investigated the total synthesis of (±)-plumbazeylanone (1), a naphthoquinone trimer based on two different pathways (I) and (II). The synthetic approach based on pathway (I) was not successful. However, the first synthesis of 1 from plumbagin (2a) was achieved by utilizing an unsymmetrical methylene-bridged dimer (20b), with a naphthoquinone unit and a naphthalene unit as a key intermediate, based on pathway (II), in 11 steps with an overall yield of 5.9%. This synthesis features regioselective nucleophilic 1,2-addition of the naphthyllithium reagent 4a to the C-1 position of naphthoquinone 20b, and the regio- and stereoselective dienonephenol-type rearrangement of the 1,2-adduct 21b (1,2-migration of the naphthyl group to the C3-position on 21b) with 2 N-NaOH.