Chemistry:Fluorenone

From HandWiki

Fluorenone is an organic compound with the chemical formula (C
6H
4)
2CO, and is a ketone with a fluorene moiety. It is a bright yellow, fluorescent solid.[1]

Synthesis and reactions

It is synthesised by aerobic oxidation of fluorene:[1]

(C
6H
4)
2CH
2 + O
2 → (C
6H
4)
2CO + H
2O

Fluorenone sustains up to four nitro groups giving 2,4,5,7-tetranitrofluorenone.[2]

Applications

Several substituted fluorenones are biologically active as antibiotic, anticancer, antiviral, or neuromodulatory compounds.[3]

Some substituted azafluorenones are biologically active, such as the naturally occurring antimicrobial compound onychine (1-methyl-4-azafluorenone).[4] The compound 1,8-diazafluoren-9-one is used for fingerprint detection.

Drugs

Fluorenone is used to synthesize:

  • A drug called IPS-339 [60979-28-4].[5]
  • An analog of 2-MDP.[6]
  • Paranyline (aka Renytoline, Mer 27).[7][8]
  • Via a Beckmann rearrangement, phenanthridone [1015-89-0]. This compound is used in the synthesis of fantridone.[9][10]
  • An analog of amitriptyline, as reported by Roche: [4684-13-3].[11][12]

See also

References

  1. ↑ 1.0 1.1 Karl Griesbaum; Arno Behr; Dieter Biedenkapp; Heinz-Werner Voges; Dorothea Garbe; Christian Paetz; Gerd Collin; Dieter Mayer et al. (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 3-527-30673-0. 
  2. ↑ Melvin S. Newman and H. Boden (1962). "2,4,5,7-Tetranitrofluorenone". Organic Syntheses 42: 95. doi:10.15227/orgsyn.042.0095. 
  3. ↑ Patel, Sagarkumar; Rathod, Bhagyashri; Regu, Siddulu; Chak, Shivam; Shard, Amit (2020). "A Perspective on Synthesis and Applications of Fluorenones". ChemistrySelect 5 (34): 10673–10691. doi:10.1002/slct.202002695. ISSN 2365-6549. 
  4. ↑ Gomes, Claudia R.B.; de Souza, Marcus V.N.; Facchinetti, Victor (2020-02-24). "A Review on Onychine and its Analogs: Synthesis and Biological Activity". Current Organic Synthesis 17 (1): 3–22. doi:10.2174/1570179417666191218112842. ISSN 1570-1794. PMID 32103713. 
  5. ↑ Soltani Rad, Mohammad Navid; Behrouz, Somayeh; Zarenezhad, Elham; Moslemin, Mohammad Hossein; Zarenezhad, Ali; Mardkhoshnood, Mehdi; Behrouz, Marzieh; Rostami, Saeid (2 March 2014). "Synthesis of fluorene and/or benzophenone O-oxime ethers containing amino acid residues and study of their cardiovascular and antibacterial effects" (in en). Medicinal Chemistry Research 23 (8): 3810–3822. doi:10.1007/s00044-014-0967-3. ISSN 1054-2523. http://link.springer.com/10.1007/s00044-014-0967-3. 
  6. ↑ Robert B Moffett, US3325544 (1967 to Pharmacia and Upjohn Co).
  7. ↑ Allen, Robert E.; Schumann, Edward L.; Day, William C.; Van Campen, M. G. (1958). "Amidines of Certain Substituted Triphenylethylenes". Journal of the American Chemical Society 80 (3): 591–598. doi:10.1021/ja01536a020.
  8. ↑ Jr Marcus G Van Campen, Robert E Allen,Frank P Palopoli, Edward L Schumann, US2877269 (1959 to Wm S Merrell Co).
  9. ↑ Cookson, R. F.; James, J. W.; Rodway, R. E.; Simmonds, R. G. (1972). "Synthesis of some phenanthridone derivatives". Journal of Heterocyclic Chemistry.9 (3): 475–480. doi:10.1002/jhet.5570090303.
  10. ↑ J. W. James and R. E. Rodway, GB1135947 (1968 to Aspro Nicholas Ltd).
  11. ↑ Dr Kurt Stach, et al. DE1150976 (1963 to Roche Diagnostics GmbH).
  12. ↑ Dr-Ing Kurt Stach, DE1211630 (1966 to Roche Diagnostics GmbH).



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