Dibenzosuberenone

Dibenzosuberenone
Names
Other names
5H-Dibenzo[a,d]cyclohepten-5-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.017.035
EC Number
  • 218-737-3
UNII
  • InChI=1S/C15H10O/c16-15-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)15/h1-10H
    Key: SNVTZAIYUGUKNI-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC3=CC=CC=C3C2=O
Properties
C15H10O
Molar mass 206.24 g/mol
Density g/cm3 (20°C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5-Dibenzosuberenone is an organic chemical with use in drug synthesis. Chemically speaking, the structure can be described as a benzophenone moiety bonded through an ethylene bridge into a seven membered ring.[1] In contrast to dibenzosuberone, dibenzosuberenone does not contain any sp3 hybridized bonds.

Applications

Dibenzosuberenone predominantly has uses in the synthesis of tricyclic antidepressants.

Synthesis

Dibenzosuberenone is made from dibenzosuberone by dehydrogenation.[15]

In an alternative method dibenzosuberone is halogenated with NBS; dehydrohalogenation then also furnishes the target molecule.[1] In an older document molecular bromine was used under irradiation. This gave a 70-90% yield of product.[16][17]

2-Carboxybenzaldehyde [119-67-5] and hydroxyphthalide [16859-59-9] exist together in a tautomeric equilibrium. Wittig reaction to this forms predominantly (Z)-2-stilbenecarboxylic acid [66374-10-5]. It is important to mention that the Z-isomer is indeed the favored product of this step and not the trans-isomer. Cyclization of the carboxylic acid in polyphosphoric acid then also forms dibenzosuberenone.[18]

References

  1. ^ a b Dastan, A., Kilic, H., Saracoglu, N. (February 2018). "The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application". Synthesis. 50 (03): 391–439. doi:10.1055/s-0036-1589518.
  2. ^ Jr Robert D Hoffsommer, Taub David, Norman L Wendler, US3272864 and US3442949 (1966 to Merck and Co Inc).
  3. ^ Chang, Meng-Yang; Huang, Yu-Ping; Lee, Tein-Wei; Chen, Yeh-Long (2012). "Synthesis of dizocilpine". Tetrahedron. 68 (16): 3283–3287. doi:10.1016/j.tet.2012.03.007.
  4. ^ Mahesh Kandula, et al. WO2013168004 (2016 to Cellix Bio Pvt Ld).
  5. ^ Ciganek, Engelbert; Uyeda, Roy T.; Cohen, Marvin; Smith, Dewey H. (1981). "Imine analogs of tricyclic antidepressants". Journal of Medicinal Chemistry. 24 (3): 336–341. doi:10.1021/jm00135a018. PMID 7265119.
  6. ^ Roy Teruyuki Uyeda, US3901945 (1975 to EIDP Inc).
  7. ^ CID 44342445 from PubChem
  8. ^ CID 9804490 from PubChem
  9. ^ Takahara, A.; Hirasawa, A.; Dohmoto, H.; Shoji, M.; Yoshimoto, R.; Sugiyama, A.; Hashimoto, K. (2001). "In vivo antiarrhythmic profile of AP-792 assessed in different canine arrhythmia models". Japanese Journal of Pharmacology. 87 (1): 21–26. doi:10.1254/jjp.87.21. PMID 11676194.
  10. ^ CID 9955277 from PubChem
  11. ^ Bernt Sigfrid Emanuel Carnmalm, et al. US3904691 (1975 to Astra Lakemedel AB).
  12. ^ Bernt Sigfrid Emanuel Carnmalm, et al. US4053632 (1977 to Astra Lakemedel AB).
  13. ^ CID 165241 from PubChem
  14. ^ CID 9805663 from PubChem
  15. ^ Stefan Lambrecht & Horst Surburg, WO2001016065 (to SYMRIS & Co KG GmbH, Symrise AG).
  16. ^ Treibs, W.; Klinkhammer, H. (6 September 1951). "Über das 2.3;6.7-Dibenz-suberon-(1), II. Mitteil.Synthese des 2.3;6.7-Dibenz-suberen-(4)-ons-(1) und des 2.3;6.7-Dibenz-suberens-(4)". Chemische Berichte. 84 (8): 671–679. doi:10.1002/cber.19510840804.
  17. ^ Hellwinkel, D.; Becker, T. (August 1989). "Transannulare Hydridverschiebung versus Cyclokondensation bei 5-(2-Biphenylyl)-10,11-dihydro-5 H -dibenzo[ a , d ]cyclohepten-5-ol-Derivaten". Chemische Berichte. 122 (8): 1595–1597. doi:10.1002/cber.19891220832.
  18. ^ Marco Thyes & Gerd Steiner, US4857658 (1989 to BASF SE).
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