SMARTS matching

User 7a4bd58ff0

09-01-2012 21:13:13



I'm writing an aldol condensation reaction, which I'd like to work with an enol or a lithium enol.  It looks a little like this: '[C:1][C;!H0:2]=[O:3].[#1,#3:7][O:6][C:5]=[C;!H0:4]>>[C:1]\[C;!H0:2]=[C;!H0:4]\[C:5]=[O:6]'


 


Naturally, I run the reaction retrosynthetically on an alpha,beta-unsaturated carbonyl and get out "[#6]CC=O" and "[#6]C(=C)O[#1,#3]".  That looks fine.  


 


Now we test the forward direction and don't get a product!  A bit of investigation shows that the pattern '[#1,#3:7][O:6][C:5]=[C;!H0:4]' does not match "[#6]C(=C)O[#1,#3]".  If I simplify my reaction to only permit an enol OR a lithium enol, then everything works (i.e., remove either the #1 or the #3 from the definition).  Is there a setting that would avoid having to duplicate these reactions?



ChemAxon e08c317633

11-01-2012 17:46:16

Reactor does not support this feature, the reactants (in molsearch terminology the targets) cannot contain list atoms.


The only solution is to remove either the #1 or the #3 from the input reactant definition.


Zsolt