116664-06-3

Basic information

• Product Name: 1,1-bis<(benzoyloxy)methyl>-2-vinylcyclopropane
• Synonyms: 1,1-bis<(benzoyloxy)methyl>-2-vinylcyclopropane
• CAS NO: 116664-06-3
• Molecular Weight: 336.387
• Mol File: 116664-06-3.mol

Chemical Properties

• CAS DataBase Reference: 1,1-bis<(benzoyloxy)methyl>-2-vinylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-bis<(benzoyloxy)methyl>-2-vinylcyclopropane(116664-06-3)
• EPA Substance Registry System: 1,1-bis<(benzoyloxy)methyl>-2-vinylcyclopropane(116664-06-3)

Safety Data

• Hazardous Substances Data: 116664-06-3(Hazardous Substances Data)

Upstream product

• 102225-94-5 (2-vinylcyclopropane-1,1-diyl)dimethanol 
• 98-88-4 benzoyl chloride 
• 7686-78-4 diethyl 2-vinylcyclopropane-1,1-dicarboxylate 

Downstream Products

• 116664-07-4 2,2-bis<(benzoyloxy)methyl>cyclopropanemethanol 
• 116664-09-6 2-amino-9-<<2,2-bis-<(benzoyloxy)methyl>cyclopropyl>methyl>-6-chloropurine 
• 116664-11-0 9-<<2,2-bis<(benzoyloxy)methyl>cyclopropyl>methyl>adenine 
• 116664-08-5 <2,2-bis<(benzoyloxy)methyl>cyclopropyl>methyl p-toluenesulfonate 

Relevant articles and documents

Metal-Free Visible-Light-Promoted Trifluoromethylation of Vinylcyclopropanes Using Pyrylium Salt as a Photoredox Catalyst

Visible-light-induced metal-free trifluoromethylation of activated, carbocyclic, and unactivated vinylcyclopropanes via a ring-opening reaction using the Langlois reagent (CF3SO2Na) is reported to synthesize allylic trifluoromethylated derivatives. Allylic trifluoromethylation was achieved by a photo-oxidative single electron transfer (SET) process at an ambient temperature and under metal-free conditions and visible-light irradiation using pyrylium salt as a photoredox catalyst. The reported methodology has an operational simplicity, broad substrate scope, high functional group tolerance, and scalability.

Photoredox catalysed allylic trifluoromethylation via ring opening of vinyl cyclopropanes using Langlois reagent

Trifluoromethylation of vinylcyclopropanes (VCPs) has been developed under mild reaction conditions to synthesize allylic trifluoromethylated derivatives with high yield and E/Z selectivity using visible light photo-redox catalysis and Langlois reagent (CF3SO2Na) as a trifluoromethylation source. Further, we demonstrate a gram scale synthesis procedure for a trifluoromethylation of vinylcyclopropane.

Synthesis and antiherpetic activity of (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds

A series of analogues of acyclovir and ganciclovir were prepared in which conformational constrainst were imposed by incorporation of a cyclopropane ring or unsaturation into the side chain. In addition, several related base-modified compounds were synthesized. These acyclonucleosides were evaluated for enzymatic phosphorylation and DNA polymerase inhibition in a staggered assay and for inhibitory activity against herpes simplex virus types 1 and 2 in vitro. Certain of the guanine or 8-azaguanine derivatives were good substrates for the viral thymidine kinase and were further converted to triphosphate, but none was a potent inhibitor of the viral DNA polymerase. Nevertheless, one member of this group, (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine (3a), displayed significant antiherpetic activity in vitro, superior to that of the corresponding cis olefin 4a. Another group, typified by (±)-9-[[(E)-2-(hydroxymethyl)cyclopropyl]methyl]adenine (17b), possessed modest antiviral activity despite an apparent inability to be enzymatically phosphorylated. The relationship of side-chain conformation and flexibility to biological activity in this series is discussed.

Purine derivatives

Purines and pyrimidines having a fused cyclopropane ring in the side chain and the heterocyclic isosteres of said purines and pyrimidines have antiviral activity, especially against viruses of the herpes class.