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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Nescafe on June 06, 2015, 12:15:07 PM

Title: Installing this group for what reason?
Post by: Nescafe on June 06, 2015, 12:15:07 PM

Hi,

Recently so the group -OCHF2 on a compound, is this a bioisostere of some sort?

Thanks!

Nescafe.

Title: Re: Installing this group for what reason?
Post by: sjb on June 06, 2015, 12:35:47 PM

Quote from: Nescafe on June 06, 2015, 12:15:07 PM

Hi,

Recently so the group -OCHF2 on a compound, is this a bioisostere of some sort?

Thanks!

Nescafe.

Probably. or to stop some metabolic pathway. What is the compound in question?

Title: Re: Installing this group for what reason?
Post by: opsomath on June 06, 2015, 01:13:54 PM

I vaguely remember a thread on In the Pipeline where this group was mentioned as being very nearly an non-electron-donating isostere for methoxy.

Title: Re: Installing this group for what reason?
Post by: pgk on June 06, 2015, 04:03:36 PM

-F is isosteric to -OH because both are isoselectronic (9 electrons) and form strong hydrogen bonds (-F hydrogen bond is stronger). Consequently, -OCHF2 can be considered isosteric of formyl ester group -OCH(=O) but stable against hydrolysis.