Viana, Hugo; Carreiro, Elisabete P.; Goth, Albertino; Bacalhau, Patricia; Caldeira, Ana Teresa; Martins, Maria do Rosario; Burke, Anthony Joseph published the artcile< Sequential alcohol oxidation/putative homo Claisen-Tishchenko-type reaction to give esters: a key process in accessing novel biologically active lactone macrocycles>, SDS of cas: 135999-16-5, the main research area is diether ester preparation acetylcholinesterase butyrylcholinesterase inhibitor; aryloxyethyl alc tandem PCC oxidation Claisen Tishchenko esterification; lactone macrocycle preparation; borylated diether ester regioselective preparation Suzuki Miyaura coupling.
Application of a sequential pyridinium chlorochromate (PCC) alc. oxidation/putative Cr-catalyzed Claisen-Tishchenko reaction of primary alcs. to provide diether-esters, e.g., I was reported. The reaction could be conducted with 1 equiv of PCC and 1 equiv of BF3·OEt2. Indications based on literature precedent were that the reaction might proceed via a sequential alc. oxidation to the aldehyde followed by a putative Cr or boron catalyzed Claisen-Tishchenko-type reaction. Using this efficient methodol., a family of novel diether-esters was synthesized in very good yields; some of these mols. were subsequently tested against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). In addition, a new synthetic strategy for the synthesis of lactone macrocycles with potential biol. activity was also disclosed. This methodol. included the regioselective borylation of the ester substrate and a subsequent Suzuki-Miyaura coupling to obtain the desired lactone macrocycle.
RSC Advances published new progress about Borylation. 135999-16-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2, SDS of cas: 135999-16-5.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary