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Sigma-Aldrich

1-(Triphenylphosphoranylidene)-2-propanone

99%

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Synonym(s):
(2-Oxopropylidene)triphenylphosphorane, Acetylmethylene-triphenylphosphorane, Methyl (triphenylphosphoranylidene)methyl ketone, NSC 407394
Linear Formula:
CH3COCH=P(C6H5)3
CAS Number:
1439-36-7
Molecular Weight:
318.35
Beilstein:
750077
EC Number:
215-878-2
MDL number:
MFCD00008774
PubChem Substance ID:
24849772
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

203-205 °C (lit.)

SMILES string

CC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C21H19OP/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-17H,1H3

InChI key

KAANTNXREIRLCT-UHFFFAOYSA-N

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Application

Reactant for:
  • Cascade reactions of enals for enantioselective synthesis of indane derivatives
  • Enantioselective conjugate addition for synthesis of α-branched indoles
  • Synthesis of 1,2-dioxanes with antitrypanosomal activity
  • Asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin
  • Domino Suzuki / Heck coupling reactions for preparation of fluorenylidenes
  • Synthesis of amphibian pyrrolizidine alkaloids via allylic aminations
  • Synthesis of silicon-containing acyclic dienone musk odorants
Wittig reagent used recently in the syntheses of functionalized pyrrolidines and cyclobutanones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis, 1359-1359 (2007)
Martin A Lovchik et al.
The Journal of organic chemistry, 72(7), 2427-2433 (2007-03-06)
Mechanistic studies on the intramolecular nucleophilic substitution with allylic rearrangement (SNi' reaction) and a new stereoselective access to substituted cyclobutanones are reported. 4,4-Dialkyl-5-oxohex-2E-en-1-yl methanesulfonates 4 were converted to 2,2-dialkyl-3-vinylcyclobutanones 6 by SNi' ring closure. The stereochemical analysis of the reaction
Liang-Chieh Chen et al.
Frontiers in pharmacology, 9, 708-708 (2018-07-19)
Alzheimer's disease (AD) is a progressive neurodegenerative disorder with multiple etiologies. Beta-amyloid (Aβ) self-aggregation and overexpression of class IIa histone deacetylases (HDACs) are strongly implicated with AD pathogenesis. In this study, a series of novel diarylheptanoid derivatives were designed, synthesized

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