All Photos(1)
Synonym(s):
(2-Oxopropylidene)triphenylphosphorane, Acetylmethylene-triphenylphosphorane, Methyl (triphenylphosphoranylidene)methyl ketone, NSC 407394
Linear Formula:
CH3COCH=P(C6H5)3
CAS Number:
Molecular Weight:
318.35
Beilstein:
750077
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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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Related Categories
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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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