55090-29-4

Upstream product

• 2222-33-5 dibenzosuberenon 
• 10354-00-4 5H-dibenzo[a,d]cyclohepten-5-ol 
• 100-58-3 phenylmagnesium bromide 
• 100-59-4 phenylmagnesium chloride 
• 1210-35-1 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one 
• 108-86-1 bromobenzene 

Downstream Products

• 19104-20-2 5-Phenyl-5H-dibenzocyclohepten 
• 84-65-1 9,10-phenanthrenequinone 
• 123613-82-1 trans-10-acetoxy-11-hydroxy-10,11-dihydrobenzocyclopenten-5-one 
• 2222-33-5 dibenzosuberenon 
• 33482-70-1 5-chloro-5-phenyl-5H-dibenzocycloheptene 
• 27915-27-1 5-Phenyl-5-azido-5H-dibenzocyclohepten 

Relevant academic research and scientific papers

Use of Charge-Charge Repulsion to Enhance π-Electron Delocalization into Anti-Aromatic and Aromatic Systems

A series of 9-fluorenyl cations has been studied and it is shown that increasing charge on a heterocyclic substituent group enhances the anti-aromatic character of the carbocation system. Similarly, a series of dibenzosuberenyl cations has been studied and increasing charge on a substituent group is shown to enhance aromatic character in the carbocation system. These studies include the direct observations of dicationic and tricationic species using stable-ion conditions and low temperature NMR. The structures of these ions were further characterized using DFT calculations, confirming that highly charged organic ions may exhibit unusual distributions of π-electrons and delocalization of electrons in 4n or 4n+2 π-systems.

Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement

Starting from benzaldehyde derivatives, the corresponding dibenzocycloheptenol could be prepared in five steps. Under both substrate (secondary vs tertiary alcohol and the substituents on the aromatic ring(s)) and condition control, the subsequent epoxidation and acid-catalyzed epoxide opening/semipinacol rearrangement/aromatization afforded the corresponding 9-anthraldehydes in good yields, up to 88% over two steps. The presence of the electron-withdrawing group(s) on the aromatic ring(s) suppressed the rate of the epoxidation while the subsequent semipinacol rearrangement step required heating; the presence of the electron-donating group(s), on the other hand, frequently led to the decomposition during the epoxidation. From the mechanistic studies, the semipinacol rearrangement of the epoxide could precede the ionization at the bisbenzylic position, yielding the aldehyde intermediate. The ensuing dehydrative aromatization led to the formation of 9-anthraldehyde. Conversely, nucleophilic addition to the aldehyde and dehydrative aromatization with concomitant loss of formic acid led to anthracene.

Investigation of the solvent enclathration potentials of 5-phenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol and related seven-membered ring alcohols

Four previously reported tricyclic alcohols containing seven-membered central B-rings, 5-phenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol, 5-phenyl-5H-dibenzo[a,d]cyclohepten-5-ol, 11-phenyl-6,11-dihydrodibenzo[b,e] oxepin-11-ol and 11-phenyl-6,11-dihydrodibenzo[b,e]thiepin-11-ol have been synthesized and their solvent enclathration (inclusion) properties investigated and compared by using 1H-NMR and differential scanning calorimetry (DSC). The presence of an oxygen or a sulphur atom, respectively, in the B-ring of the latter two compounds had a detrimental effect on the solvent enclathration properties of the host compounds as compared to those containing an ethane or ethylene bridge. This suggests that, although enclathration is highly dependent on the hydrogen bonding ability of the host, rigidity of the structure plays a crucial role in the formation and stability of these complexes.

Tricylic amino-acid derivatives

Described herein are compounds which have the general formula: or a prodrug or pharmaceutically acceptable salt, solvate or hydrate thereof wherein: R1 is selected from the group consisting of H, alkyl and the counter ion for a basic addition salt; X is selected from the group consisting of CR9R10, S, O, SO, SO2, NH and N-alkyl; R2, R3, R4, R9 and R10 are independently selected from the group consisting of H and alkyl; R5 and R6 are independently selected from the group consisting of H, alkyl and phenyl, or, alternatively, R5 and R6 together may form a methylene group or a 3- to 6-membered a spirocyclic group; wherein, when X is CR9R10, one or both pairs of R5 and R9 or R6 and R10 may join to form a double or triple bond R7 is selected from the group consisting of Formula II-V: which are all optionally substituted, at nodes other than R8, with 1-4 substituents independently selected from the group consisting of alkyl, halo, aryl (which may be substituted as for R8), trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, mono-alkylamino, di-alkylamino, alkoxycarbonyl, alkylcarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl, alkoxy, alkylS-, phenoxy, -SO2NH2, -SO2NHalkyl, -SO2N(alkyl)2 and 1,2-methylenedioxy; and wherein any of the benzo-fused rings in structures II to V may be replaced by a 5- or 6-membered heterocyclic ring selected from the group consisting of pyridine, thiophene, furan and pyrrole; wherein R8 is selected from the group consisting of H, alkyl, benzyl, cycloalkyl, indanyl and an optionally substituted aryl group, wherein the optional substituents are independently selected from 1-4 members of the group consisting of alkyl, halo, aryl, trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, mono-alkylamino, di-alkylamino, alkoxycarbonyl, alkylcarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl, alkoxy, alkylS-, phenoxy, -SO2NH2, -SO2NHalkyl, -SO2N(alkyl)2 and 1,2-methylenedioxy; -represents a single or double bond; Y is selected from the group consisting of O, S, SO, NH, N-alkyl, CH2, CH-alkyl, C(alkyl)2, and C=O; Z is selected from the group consisting of CH2, O, S, NH and N-alkyl when-is a single bond; Z is selected from the group consisting of CH and N when-is a double bond. Also described is the use of these compounds as pharmaceuticals.

Ritter Reactions. IX. Transannular Addition of Nitriles to the 5H-Dibenzocycloheptene Ring System

The 5H-dibenzocyclohepten-5-ols (1a-e) undergo sequential intramolecular and conventional Ritter reactions with acetonitrile to afford the cyclohepten-11-yl>acetamides (6a-e).Typical yields for these one-flask conversions are 52-64percent, except for the reaction of (1a) where production of the dimeric substance (4a) is favoured.Alcohol (1a) can provide either type of product in good yield, depending on the conditions employed, when reacted with benzonitrile.The molecular skeleton present in the adducts (6) has been confirmed by determination of the crystal structure of (6c) , a 9.188(3), b 14.632(5), c 16.563(9) Angstroem, α 115.64(9), β 90.92(2), γ 96.29(2) deg, Z 4, R 0.043>.

Versatile and Convenient Lattice Hosts derived from Singly Bridged Triarylmethane Frameworks, X-Ray Crystal Structures of Three Inclusion Compounds

A new family of host molecules, based on the singly bridged triarylmethanol and triarylacetic acid frameworks, is described.These hosts form crystalline inclusions with a variety of uncharged organic molecules ranging from protic dipolar to apolar compounds (130 different species).The formation and stoicheiometry depend in a systematic manner on structural parameters of the host, such as the nature of the functional group and the substituents, and on the substituent positions.The crystal structures of three inclusion compounds have been studied by X-ray diffraction.They reveal the building principles of the new inclusion family.In the crystals of 1a*benzene (8:3), the benzene is interstitially entrapped by H-bonded tetramer clusters of 1a.Crystals of 1a*dioxane (4:3) are built of H-bonded 2:1 host-guest complexes including interstitial molecules of dioxane.In the case of 4c*EtOH (1:1), the building principle is formation of 2:2 host-guest clusters via a twelve-membered H-bonded ring.

Synthesis of o-Substituted Phenols by Criegee Rearrangement of Benzylic Hydroperoxides

9-Phenylthioxanthen-9-ol, 10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol, and 9-arylfluoren-9-ols undergo Criegee-type rearrangements when treated with hydrogen peroxide and acid to generate substituted benzophenones from the first two substrates, and monoesters of biphenyl-2,2'-diol from the fluorenes via subsequent Bayer-Villiger oxidation of the intermediate 2'-aroylbiphenyl-2-ol. 5-Phenyl-10,11-dihydrodibenzocyclohepten-5-ol and its dehydroderivative gave the corresponding heptanone and heptenone on treatment with acid and hydrogen peroxide.Prolonged reaction of the 5-phenyldibenzohepten-5-ol afforded products arising from oxidation of the double bond.