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All posts Subject: internal ring closure/dehydration: phenylalanine Please login to post

stratosphere
(Hive Bee)
01-13-04 18:23
No 482213
internal ring closure/dehydration: phenylalanine
(Rated as: smiles code error)

according to an article* i saw referenced in my chem book, beta-phenyl propanoic acid undergoes an internal ring closure/dehydration to yeild 1-indanone when treated with HF, i.e.

b-phenylpropanoic acid --HF-> 1-indanone

*fieser+hershberg, J. Am. Chem. Soc.,61,1272(1939)

if one were to assume that N protonated phenylalanine (phenylalanine.HF) were to react in similiar manner as b-phenylpropanoic acid, this would be an interesting route to 2-amino-1-indanone, which would bare many similarities to cathinone.

any insight as to how the alpha NH3+ would effect the outcome of this reaction, or if it succeded, the cns activity of the resultant compound?

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	All posts		Subject: internal ring closure/dehydration: phenylalanine		Please login to post


		stratosphere (Hive Bee) 01-13-04 18:23 No 482213				internal ring closure/dehydration: phenylalanine (Rated as: smiles code error)
						according to an article* i saw referenced in my chem book, beta-phenyl propanoic acid undergoes an internal ring closure/dehydration to yeild 1-indanone when treated with HF, i.e. b-phenylpropanoic acid --HF-> 1-indanone *fieser+hershberg, J. Am. Chem. Soc.,61,1272(1939) if one were to assume that N protonated phenylalanine (phenylalanine.HF) were to react in similiar manner as b-phenylpropanoic acid, this would be an interesting route to 2-amino-1-indanone, which would bare many similarities to cathinone. any insight as to how the alpha NH3+ would effect the outcome of this reaction, or if it succeded, the cns activity of the resultant compound?

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