63818-65-5

Upstream product

• 21778-19-8 (4-methoxyphenyl)phosphonic acid 
• 78-39-7 Triethyl orthoacetate 
• 37632-18-1 4-methoxyphenylphosphonic dichloride 
• 3762-33-2 diethyl (p-methoxyphenyl)phosphonate 

Downstream Products

• 362477-53-0 (4-methoxyphenyl)chlorophosphonic acid ethyl ester 
• 1443991-83-0 3-phenyl-4-methyl-1-ethoxy-6-methoxy-benz[c-1,2]oxaphosphinine 1-oxide 
• 1443991-81-8 3,4-diphenyl-1-ethoxy-6-methoxy-benz[c-1,2]oxaphosphinine 1-oxide 
• 362476-85-5 (3R)-N-benzyloxy-2-[(RS)-ethoxy(4-methoxyphenyl)phosphoryl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 

Relevant academic research and scientific papers

Selective esterification of phosphonic acids

Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.

Synthesis of phosphaisocoumarins through rhodium-catalyzed cyclization using alkynes and arylphosphonic acid monoesters

A rhodium-catalyzed cyclization using alkynes and arylphosphonic acid monoesters for the synthesis of phosphaisocoumarins is reported. A number of arylphosphonic acid monoesters were selectively cyclized in high yields with functional group tolerance. In addition, unsymmetrical alkynes are applied in high regioselectivity.

Encounter with unexpected collagenase-1 selective inhibitor: Switchover of inhibitor binding pocket induced by fluorine atom

Phosphonamide-based inhibitors having trifluoromethyl moiety showed highly selective inhibition against MMP-1. A possible mechanism of the selectivity of MMP-1 inhibitors through the switchover of the binding pocket was speculated by computational calculations. As a consequence of the unexpected selectivity, the specific interaction of CF3 group of the inhibitor and Arg214 in the S1′ pocket of MMP-1 conducted a low binding energy.