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Topic: Installing this group for what reason?  (Read 2662 times)

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Offline Nescafe

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Installing this group for what reason?
« 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.
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Offline sjb

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Re: Installing this group for what reason?
« Reply #1 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?
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Offline opsomath

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Re: Installing this group for what reason?
« Reply #2 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.
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Offline pgk

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Re: Installing this group for what reason?
« Reply #3 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.
« Last Edit: June 06, 2015, 04:15:06 PM by pgk »
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