Catalog Number
ACM1067874-2
Product Name
Diethyl Allylphosphonate
IUPAC Name
3-diethoxyphosphorylprop-1-ene
Molecular Weight
178.17g/mol
Molecular Formula
C7H15O3P
Canonical SMILES
CCOP(=O)(CC=C)OCC
InChI
InChI=1S/C7H15O3P/c1-4-7-11(8,9-5-2)10-6-3/h4H,1,5-7H2,2-3H3
InChI Key
YPJHXRAHMUKXAE-UHFFFAOYSA-N
Application
Diethyl allylphosphonate serves as a versatile reactant in various chemical transformations, predominantly involving C-C bond formation. It is especially notable for its role in the copolymerization of phosphonated allyl monomers with maleic anhydride, as well as in the enantioselective synthesis of solamin-type mono-THF acetogenins. Furthermore, it facilitates ring-closing metathesis (RCM) reactions to produce oxaphospholene and oxaphosphinene heterocycles, and is instrumental in the synthesis of complex natural products such as spongistatin 2 through Wittig coupling. Its utility extends to the stereoselective synthesis of pentacyclic furanosteroids and the preparation of protected polyhydroxylated β-amino acid constituents of microsclerodermins. The compound diethyl allylphosphonate is thus vital in advanced organic synthesis, enabling the construction of diverse molecular architectures with precision and efficiency.
Covalently-Bonded Unit Count
1
Exact Mass
178.075881g/mol
Monoisotopic Mass
178.075881g/mol