Cis-1,2-Dihydrocatechol

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cis-1,2-Dihydrocatechol
Cis-1,2-Dihydrocatechol.svg
Names
IUPAC name
3,5-Cyclohexadiene-1,2-diol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
200913
KEGG
PubChem CID
  • InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-8H/t5-,6+
    Key: YDRSQRPHLBEPTP-OLQVQODUSA-N
  • C1=C[C@H]([C@H](C=C1)O)O
Properties
C6H8O2
Molar mass 112.128 g·mol−1
Appearancewhite oily solid
Melting point 28 °C (82 °F; 301 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

cis-1,2-Dihydrocatechol is the organic compound with the formula C6H6(OH)2. Several isomers exist with this formula. It is a colorless solid melting near room temperature. The compound is classified as a 1,3-cyclohexadiene. It arises by the dihydroxylation of benzene catalyzed by toluene dioxygenase. It can also be prepared from catechol using the enzyme cis-1,2-dihydrobenzene-1,2-diol dehydrogenase: [1] [2]

cis-1,2-Dihydrocatechol has been used in the synthesis, sometimes on a commercial scale, of indinavir, indigo, and poly(p-phenylene). [3]

References

  1. ↑ Axcell BC, Geary PJ (1973). "The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase)". Biochem. J. 136 (4): 927–34. doi:10.1042/bj1360927. PMC   1166042 . PMID   4362337.
  2. ↑ Gibson DT, Koch JR, Kallio RE (1968). "Oxidative degradation of aromatic hydrocarbons by microorganisms. I Enzymatic formation of catechol from benzene". Biochemistry. 7 (7): 2653–62. doi:10.1021/bi00847a031. PMID   4298226.
  3. ↑ Hudlicky, Tomas; Thorpe, Andrew J. (1996). "Current Status and Future Perspectives of Cyclohexadiene-cis-diols in Organic Synthesis: Versatile Intermediates in the Concise Design of Natural Products". Chemical Communications (17): 1993. doi:10.1039/cc9960001993.
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