1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one

• ChemBase ID: 74878
• Molecular Formular: C21H19OP
• Molecular Mass: 318.348721
• Monoisotopic Mass: 318.11735186
• SMILES: P(=CC(=O)C)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: CC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: 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
• InChIKey: KAANTNXREIRLCT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one; 1-(triphenyl-λ^5-phosphanylidene)propan-2-one
• IUPAC Traditional name: 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one; 1-(triphenyl-λ^5-phosphanylidene)propan-2-one
• Synonyms: (Methylcarbonylmethylene)triphenylphosphorane; (Acetylmethylene)triphenylphosphorane; (2-Oxopropylidene)triphenylphosphorane; Methyl (triphenylphosphoranylidene)methyl ketone; NSC 407394; Acetylmethylene-triphenylphosphorane; 1-(Triphenylphosphoranylidene)-2-propanone; 1-TRIPHENYLPHOSPHORANYLIDENE-2-PROPANONE; (Acetylmethylene)triphenylphosphorane; 1-(Triphenylphosphoranylidene)propan-2-one; 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one; 1-(Triphenylphosphoranylidene)-2-propanone; (Acetonylidene)triphenylphosphorane; Triphenyl(acetylmethylene)phosphorane; (乙酰亚甲基)三苯基磷烷; 1-三苯基膦-2-丙酮; (乙酰亚甲基)三苯基磷烷

Database IDs

• CAS Number: 1439-36-7
• EC Number: 215-878-2
• MDL Number: MFCD00008774
• Beilstein Number: 750077
• PubChem SID: 162039796; 24849772; 24845159
• PubChem CID: 15038

CALCULATED PROPERTIES

• Acid pKa: 19.161655
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.7111
• LogD (pH = 7.4): 5.7111
• Log P: 5.7111
• Molar Refractivity: 97.2311 cm^3
• Polarizability: 38.120384 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 203 - 205°C; 203-205 °C(lit.); 204-209°C; 205-207 °C
• Hydrophobicity(logP): 5.704

Safety Information

• Storage Warning: Air Sensitive
• RTECS: UC3900000
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (NT); 95%; 98%; 99%
• Grade: purum
• Linear Formula: CH3COCH=P(C6H5)3

DETAILS

MP Biomedicals - 05218547

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 158755

Application
Wittig reagent used recently in the syntheses of functionalized pyrrolidines8 and cyclobutanones.9
Reactant for:
• Cascade reactions of enals for enantioselective synthesis of indane derivatives1
• Enantioselective conjugate addition for synthesis of α-branched indoles2
• Synthesis of 1,2-dioxanes with antitrypanosomal activity3
• Asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin4
• Domino Suzuki / Heck coupling reactions for preparation of fluorenylidenes5
• Synthesis of amphibian pyrrolizidine alkaloids via allylic aminations6
• Synthesis of silicon-containing acyclic dienone musk odorants7
Packaging
25, 100 g in poly bottle

Sigma Aldrich - 01340

Application
Reactant for:
• Cascade reactions of enals for enantioselective synthesis of indane derivatives1
• Enantioselective conjugate addition for synthesis of α-branched indoles2
• Synthesis of 1,2-dioxanes with antitrypanosomal activity3
• Asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin4
• Domino Suzuki / Heck coupling reactions for preparation of fluorenylidenes5
• Synthesis of amphibian pyrrolizidine alkaloids via allylic aminations6
• Synthesis of silicon-containing acyclic dienone musk odorants7

Toronto Research Chemicals - A186680

Wittig Reagent

REFERENCES

• Yang, Z., et al.: Bioorg. Med. Chem., 17, 1071 (2009)
• Shearman, G., et al.: J. Mat. Chem., 19, 598 (2009)
• Stabilized ylide which converts aldehydes to methyl ɑ?-enones (see Appendix 1). Metallation with n-BuLi and alkylation, followed by Wittig reaction with an aldehyde provides a route to ɑ?-unsaturated ketones: J. Org. Chem., 38, 4082 (1973); Synth. Commun., 8, 579 (1979):
  
• For C-acylation followed by oxidation of the resulting diacylphosphoranes to give 1,2,3-triketones, see N,O-Bis(trimethylsilyl)acetamide, L00183.