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.

  1. Citenamide
  2. Cyclobenzaprine
  3. Cyproheptadine
  4. Demexiptiline
  5. Dinorcyclobenzaprine:[2]
  6. Dizocilpine[3]
  7. Intriptyline
  8. Mariptiline
  9. Norcyclobenzaprine [303-50-4][4]
  10. Norcyproheptadine [14051-46-8]
  11. Octriptyline
  12. Octripyline imine (6 times the potency of amitriptyline)[5][6]
  13. Protriptyline
  14. Zosuquidar
  15. AH-1058 [300347-11-9]
  16. AP-792[7]
  17. CPG 146 [41695-43-6], CPG 147 [41695-46-9], CPG 148, CPG 186, CPG 191 [41695-49-2], CPG 264 [41695-45-8]:[8][9]
  18. Wy-41770 [4517-99-1]
  19. AT 1015 [190508-50-0]

Synthesis

Dibenzosuberenone is made from dibenzosuberone by dehydrogenation.[10]

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.[11][12]

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.[13]

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. ^ 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.
  8. ^ Bernt Sigfrid Emanuel Carnmalm, et al. US3904691 (1975 to Astra Lakemedel AB).
  9. ^ Bernt Sigfrid Emanuel Carnmalm, et al. US4053632 (1977 to Astra Lakemedel AB).
  10. ^ Stefan Lambrecht & Horst Surburg, WO2001016065 (to SYMRIS & Co KG GmbH, Symrise AG).
  11. ^ 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.
  12. ^ 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.
  13. ^ Marco Thyes & Gerd Steiner, US4857658 (1989 to BASF SE).
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