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.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. In contrast to dibenzosuberone, dibenzosuberenone does not contain any sp3 hybridized bonds. Applications Dibenzosuberenone predominantly has uses in the synthesis of tricyclic antidepressants. Citenamide Cyclobenzaprine Cyproheptadine Decitropine Demexiptiline DinorcyclobenzaprineJr Robert D Hoffsommer, Taub David, Norman L Wendler, US3272864 and US3442949 (1966 to Merck and Co Inc). Dizocilpine Intriptyline Mariptiline Norcyclobenzaprine [303-50-4]Mahesh Kandula, et al. WO2013168004 (2016 to Cellix Bio Pvt Ld). Norcyproheptadine [14051-46-8] Octriptyline Octripyline imine (6 times the potency of amitriptyline)Roy Teruyuki Uyeda, US3901945 (1975 to EIDP Inc). Protriptyline Zosuquidar AH-1058 [300347-11-9] AP-792 CPG 146 [41695-43-6], CPG 147 [41695-46-9], CPG 148, CPG 186, CPG 191 [41695-49-2], CPG 264 [41695-45-8]Bernt Sigfrid Emanuel Carnmalm, et al. US3904691 (1975 to Astra Lakemedel AB).Bernt Sigfrid Emanuel Carnmalm, et al. US4053632 (1977 to Astra Lakemedel AB). Wy-41770 [4517-99-1] AT 1015 [190508-50-0] MK-940 PC21125987 [5154-92-7]E Christy Marcia, GB1074081 (1967 to Merck and Co Inc).
Synthesis Dibenzosuberenone is made from dibenzosuberone by dehydrogenation.Stefan Lambrecht & Horst Surburg, WO2001016065 (to SYMRIS & Co KG GmbH, Symrise AG).
In an alternative method dibenzosuberone is halogenated with NBS; dehydrohalogenation then also furnishes the target molecule. In an older document molecular bromine was used under irradiation. This gave a 70-90% yield of product.
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.Marco Thyes & Gerd Steiner, US4857658 (1989 to BASF SE).
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