1253203-72-3

Basic information

• Product Name: 1,8-dibenzyl-1,8-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d:5,6-d']bis([1,2,3]triazole)
• Synonyms: 1,8-dibenzyl-1,8-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d:5,6-d']bis([1,2,3]triazole)
• CAS NO: 1253203-72-3
• Molecular Weight: 466.545
• Mol File: 1253203-72-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,8-dibenzyl-1,8-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d:5,6-d']bis([1,2,3]triazole)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-dibenzyl-1,8-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d:5,6-d']bis([1,2,3]triazole)(1253203-72-3)
• EPA Substance Registry System: 1,8-dibenzyl-1,8-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d:5,6-d']bis([1,2,3]triazole)(1253203-72-3)

Safety Data

• Hazardous Substances Data: 1253203-72-3(Hazardous Substances Data)

Upstream product

• 53397-65-2 sym-dibenzo-1,5-cyclooctadiene-3,7-diyne 
• 622-79-7 benzyl azide 
• 1027338-06-2 4-dibenzocyclooctynol 
• 468751-39-5 5,11-bis(phenylsulfonyl)dibenzo[a,e][8]annulene 
• 468751-38-4 ortho-(phenylsulfonylmethyl)benzaldehyde 
• 82651-72-7 ortho-(phenylsulfonylmethyl)benzonitrile 

Relevant articles and documents

Water-soluble, stable and azide-reactive strained dialkynes for biocompatible double strain-promoted click chemistry

The Sondheimer dialkyne is extensively used in double strain-promoted azide-alkyne cycloadditions. This reagent suffers with poor water-solubility and rapidly decomposes in aqueous solutions. This intrinsically limits its application in biological systems, and no effective solutions are currently available. Herein, we report the development of novel highly water-soluble, stable, and azide-reactive strained dialkyne reagents. To demonstrate their extensive utility, we applied our novel dialkynes to a double strain-promoted macrocyclisation strategy to generate functionalised p53-based stapled peptides for inhibiting the oncogenic p53-MDM2 interaction. These functionalised stapled peptides bind MDM2 with low nanomolar affinity and show p53 activation in a cellular environment. Overall, our highly soluble, stable and azide-reactive dialkynes offer significant advantages over the currently used Sondheimer dialkyne, and could be utilised for numerous biological applications.

Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes

Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.