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Allyldiphenylphosphine Oxide

Catalog Number
ACM4141484-1
Product Name
Allyldiphenylphosphine Oxide
Structure
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CAS
4141-48-4
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Synonyms
ACMC-1APXU; I14-102028; Diphenyl-2-propenylphosphine oxide; Allyl(diphenyl)phosphine oxide; [allyl(phenyl)phosphoryl]benzene; FT-0635149; Allyldiphenylphosphineoxide; KS-000015MZ; PGPAPANRSWMTQO-UHFFFAOYSA-N; Allyldiphenylphosphine oxide;
IUPAC Name
[phenyl(prop-2-enyl)phosphoryl]benzene;
Molecular Weight
242.258g/mol
Molecular Formula
C15H15OP;
Canonical SMILES
C=CCP(=O)(C1=CC=CC=C1)C2=CC=CC=C2;
InChI
InChI=1S/C15H15OP/c1-2-13-17(16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h2-12H,1,13H2;
InChI Key
PGPAPANRSWMTQO-UHFFFAOYSA-N;
Complexity
263
Covalently-Bonded Unit Count
1
Exact Mass
242.086g/mol
H-Bond Acceptor
1
Heavy Atom Count
17
Monoisotopic Mass
242.086g/mol
NSC Number
98715
Rotatable Bond Count
4
Topological Polar Surface Area
17.1A^2
Application
Allyldiphenylphosphine Oxide serves as a versatile reactant in various advanced chemical processes. It is primarily used in the preparation of α-substituted alkylsilanes through a regio- and chemoselective copper-catalyzed silylzincation and electrophilic substitution from terminal alkenes, and in the synthesis of α-substituted alcohols via Fleming-Tamao oxidation of alkylsilanes. Additionally, it plays a crucial role in olefin isomerization using Grubbs' catalysts embedded in a hydrophobic polydimethylsiloxane (PDMS) matrix. The compound is also vital for producing C9-substituted trans-hydrindene through a diastereotopic group-selective intramolecular Diels-Alder reaction and facilitates the isomerization of allyl group-containing compounds to propenyl group-containing compounds with a Grubbs second-generation ruthenium catalyst. Moreover, it is essential in ruthenium-catalyzed olefin cross-metathesis of vinyl and allyl phosphine oxides, yielding alkenyl phosphine oxides and bis-phosphine oxides.
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