Chem 634, Advanced Organic Chemistry- Synthesis and ReactivityProf. Joseph FoxChemical Database Searching- Handout 6 Handout 6: Functional Group mapping using BeilsteinIn this tutorial, we will demonstate how to use Beilstein to search with reaction mapping. For thisspecific search, we will search for reactions of the type below, to find if derivatives of amino acidscan be prepared by oxidation of a phenyl group. We will proceed by telling the database that wewant the quaternary carbon of the phenyl group to end up as the carbonyl carbon of the acid.NR2R ROOHNR2R RNOTE: searches of this type, while useful, are far from perfect. Remember, this database is onlyas good as the person entering the information! These searches can also tend to be timeconsuming. Thus, for reaction mapping it is often more useful to conduct searches asdemonstrated in Scheme 5 where we exercise a little patience in skimming through the hits.1. Begin by drawing the picture shown below, as we have done before2. In reaction editor mode, select the pencil3. Draw a line that connects the quaternary phenyl carbon with the carbonyl carbon of the product.4. You should see a dashed line connecting these atoms. This tells the database that this carbonof the reactant is that same carbon atom in the product5. Begin the search6. This search produces 40 hits. Try selecting hit #147. Here we see an example of using RuCl3, NaIO4 to oxidize a phenyl to a carboxylic acid toproduce a protected amino acid
View Full Document
Unlocking...