Naphthoquinone

Naphthoquinone is a class of organic compounds derived from naphthalene. Three isomers are normally discussed:

• 1,2-Naphthoquinone
• 1,4-Naphthoquinone, of which the Vitamin K group compounds are derivatives
• 2,6-Naphthoquinone (amphi-naphthoquinone)

Naphthoquinones are also a class of natural phenolic compounds formed on a C6-C4 skeleton.

Natural products

Juglone, a compound found in black walnut

• Alkannin
• Hexahydroxy-1,4-naphthalenedione
• Juglone
• Lapachol
• Lawsone
• Menatetrenone
• 2-Methoxy-1,4-naphthoquinone, a compound found in Impatiens species
• Nigrosporin B
• 2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione
• Phylloquinone
• Plumbagin
• 2,3,5,7-Tetrahydroxy-1,4-naphthalenedione

Synthetic chemicals

• Menadione
• 5,8-Dihydroxy-1,4-naphthoquinone and dihydroxynaphthoquinones
• Atovaquone

Uses as chemical precursors

Naphthoquinone can be used for the full synthesis of opiates (Gates synthesis), but it is a tedious and uneconomical process. Therefore, most of the opiate-type analgesics in use today are either directly extracted from Papaver somniferum or synthesized from the natural opiates, mainly from thebaine.^[1]

Diazonaphthoquinone is a diazo derivative of naphthoquinone.

See also

• Hydroxynaphthoquinones
• List of biomolecules

References

1. Synthesis of morphine alkaloids Presentation School of Chemical Sciences, University of Illinois at Urbana-Champaign retrieved 12-02-2010