3111-86-2

Upstream product

• 2222-33-5 dibenzosuberenon 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1460-59-9 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene 
• 91-13-4 α,α'-dibromo-o-xylene 
• 1144-71-4 3-hydroxy-1,2:5,6-dibenzocycloocta-1,5,7-triene 

Downstream Products

• 53397-66-3 5,6-didehydrodibenzocyclo-octene 
• 1027338-09-5 11,12-didehydro-5,6-dihydrodibenzo[a,e]cycloocten-5-yl carbonic acid 4-nitrophenyl ester 
• 1027338-06-2 4-dibenzocyclooctynol 
• 1331784-24-7 C₄₁H₄₈N₈O₆S 
• 1331784-23-6 C₄₀H₄₇N₇O₆S 
• 1331784-22-5 C₂₅H₂₀N₄O₃ 
• 1253203-68-7 1-benzyl-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazol-8(9H)-one 
• 1331784-21-4 C₂₇H₂₆N₄O₃ 
• 1253203-66-5 1-benzyl-8,9-dihydro-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazol-8-ol 
• 1830-65-5 Dibenzocycloocten-5,6-dion 

Relevant academic research and scientific papers

Alkynyldicobalt derivatives of dibenzosuberenol and dibenzocyclooctatrien-5-ol: Ring conformations, ease of carbonyl elimination and relevance to pauson-khand cyclization

Under very mild conditions, (5-alkynyl-5H-dibenzo-[a,d]cycloheptatrien-5-ol)Co2(CO)6 clusters 1 lose a carbon monoxide ligand and form the corresponding η2-alkene-μ-alkyne-Co2(CO)5 complexes 2 (the first isolated examples of the initial phase of the Pauson-Khand reaction). This behaviour is not paralleled by the homologue in which an additional methylene group has been inserted within the seven-membered ring, as in the [5-alkynyl-6H-dibenzo[a,e]cyclooctatrienol]Co2-(CO)6 system 8, for which several X-ray crystal structures are reported. The apparent additional flexibility of this molecular framework does not translate into conformations appropriate for the formation of η2-alkene-μ-alkyne-Co2(CO)5 complexes. The relative inertness of the ethynyl complex 1a, compared with the ease of carbonyl loss in the trimethylsilylethynyl-and the tri(isopropyl)silylethynyl-substituted hexacarbonyldicobalt clusters, 1b and 11, respectively, is discussed in terms of outof-plane angle strain within the dibenzo[a,d]cycloheptatrienyl moiety. Comparison of the changing conformations of the seven-membered ring in a series of free and complexed molecules reveals a marked flattening of the organic framework, as bulkier substituents are incorporated at C5. The possibility of η2-alkene-μ-alkyne-Co2(CO)5 clusters functioning as hemilabile systems was explored by monitoring the ease of carbonyl substitution by triphenylphosphine in 2b (alkynyl substituent C≡CSiMe3).

Phosphodiesters as GPR84 Antagonists for the Treatment of Ulcerative Colitis

GPR84 is a proinflammatory G protein-coupled receptor associated with several inflammatory and fibrotic diseases. GPR84 antagonists have been evaluated in clinical trials to treat ulcerative colitis, idiopathic pulmonary fibrosis, and nonalcoholic steatohepatitis. However, the variety of potent and selective GPR84 antagonists is still limited. Through high-throughput screening, a novel phosphodiester compound hit 1 was identified as a GPR84 antagonist. The subsequent structural optimization led to the identification of compound 33 with improved potency in the calcium mobilization assay and the ability to inhibit the chemotaxis of neutrophils and macrophages upon GPR84 activation. In a DSS-induced mouse model of ulcerative colitis, compound 33 significantly alleviated colitis symptoms and reduced the disease activity index score at oral doses of 25 mg/kg qd, with an efficacy similar to that of positive control 5-aminosalicylic acid (200 mg/kg, qd, po), suggesting that compound 33 is a promising candidate for further drug development.

Fluorodibenzocyclooctynes: A Trackable Click Reagent with Enhanced Reactivity

Bioorthogonal reactions have widespread applications in biological systems, and development of new bioorthogonal reactions has been of great interest over the past two decades. In this work, the design and synthesis of a family of fluorinated dibenzocyclooctynes (FDIBOs) are reported. The electron-deficient nature of fluorine atoms significantly accelerated the reaction of cyclooctynes in 1,3-dipolar cycloadditions, with either benzyl azide or ethyl diazoacetate, compared to conventional dibenzocyclooctyne (DIBO). In addition, FDIBOs showed unique trackable properties owing to the high NMR sensitivity of the naturally abundant 19F isotope. Biological molecules, including a monosaccharide, a peptide, and a protein, were tested with FDIBOs, and these reactions could be easily monitored by 19F NMR spectroscopy to evaluate the progress of the conjugation reactions. In addition, labeling of live cells was also demonstrated with metabolically modified bacteria to expand the possible applications of FDIBOs.

Amine-Borane Dehydrogenation and Transfer Hydrogenation Catalyzed by α-Diimine Cobaltates

Anionic α-diimine cobalt complexes, such as [K(thf)1.5{(DippBIAN)Co(η4-cod)}] (1; Dipp=2,6-diisopropylphenyl, cod=1,5-cyclooctadiene), catalyze the dehydrogenation of several amine-boranes. Based on the excellent catalytic properties, an especially effective transfer hydrogenation protocol for challenging olefins, imines, and N-heteroarenes was developed. NH3BH3 was used as a dihydrogen surrogate, which transferred up to two equivalents of H2 per NH3BH3. Detailed spectroscopic and mechanistic studies are presented, which document the rate determination by acidic protons in the amine-borane.

ALKYNES AND METHODS OF REACTING ALKYNES WITH 1,3-DIPOLE-FUNCTIONAL COMPOUNDS

1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also di

Strain-Promoted Alkyne-Azide Cycloadditions (SPAAC) Reveal New Features of Glycoconjugate Biosynthesis

We have shown that 4-dibenzocyclooctynol (DIBO), which can easily be obtained by a streamlined synthesis approach, reacts exceptionally fast in the absence of a CuI catalyst with azido-containing compounds to give stable triazoles. Chemical mod

An efficient synthesis of dibenzocycloocta-4a,6a,-diene-5,11-diyne and its precursors

Two efficient syntheses of dibenzocyclooctadienediyne 1 were developed employing known reactions, which utilize commercially available reagents. Both methods are an improvement on known syntheses resulting in 41% and 43% overall yields. The latter method also offers an efficient synthesis of dibenzocyclooctatetraene 9, which is one of the key reagents now commercially unavailable.

Flow-vacuum pyrolysis of two related tetrazoles with fused dibenzoazonine skeletons

The flow-vacuum pyrolyses of 13,14-dihydro-8H-tetrazolo[1,5a]dibenzoazonine (14) and 8H-tetrazolo[1,5a]dibenzoazonine (10) at 1 Torr and 500°C respectively 375°C were studied by GC/MS. The main reaction product of 14 is the ring contracted 5,6,11,12-tetrahydro-dibenzo[b,f]azocine-5-carbonitrile (16) whereas the main product of the very complex reaction mixture of 10 is the stable aromatic dibenzo[b,f] [1,8]naphtyridine (22). The reaction mechanism for the middle ring saturated tetrazole 14 includes the ring contraction of the initial nitrene whereas in the case of middle ring conjugated tetrazole 10 it includes a set of thermally allowed concerted processes of the intermediate carbodiimide 18. The experimental data confirm the generality of these mechanisms by comparison with the known pyrolyses of lower homologs of 14 and 10 containing fused dibenzoazocine moieties.