Diethyl Allylphosphonate

Name: Diethyl Allylphosphonate
SKU: ACM1067874-2
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Catalog NumberACM1067874-2

CAS Number1067-87-4

CategoryMonomers

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.

Complexity

146

Covalently-Bonded Unit Count

EC Number

619-646-5

Exact Mass

178.075881g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

178.075881g/mol

Rotatable Bond Count