40780-08-3

Upstream product

• 2214-14-4 (1-methylcyclopropyl)benzene 
• 98-83-9 isopropenylbenzene 
• 75-11-6 diiodomethane 
• 6888-79-5 4-bromo-α-methylstyrene 
• 99-90-1 para-bromoacetophenone 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 867256-51-7 4'-cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester 
• 1264296-84-5 (4-(1-methylcyclopropyl)phenyl)boronic acid 
• 1431616-25-9 6-(4-(1-methylcyclopropyl)phenyl)nicotinonitrile 

Relevant academic research and scientific papers

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidases SpsB and/or LepB, an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.

B(C6F5)3-Catalyzed Ring Opening and Isomerization of Unactivated Cyclopropanes

Catalytic amounts of B(C6F5)3 promote the ring opening and subsequent isomerization of a series of unactivated cyclopropanes to afford terminal olefins in good yields when a hydrosilane and 2,6-dibromopyridine are employed as additives.

Metabolically stable tert-butyl replacement

Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp3 C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.