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Thermo Scientific Chemicals
(Acetylmethylene)triphenylphosphorane, 99%
CAS: 1439-36-7 | C21H19OP | 318.36 g/mol
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化學識別
CAS1439-36-7
IUPAC Name1-(triphenyl-λ⁵-phosphanylidene)propan-2-one
Molecular FormulaC21H19OP
InChI KeyKAANTNXREIRLCT-UHFFFAOYSA-N
SMILESCC(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
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規格
規格表
規格表Assay (HPLC)≥98.5%
Appearance (Color)White to cream
FormCrystals or powder or crystalline powder
Water Content (Karl Fischer Titration)≤0.5%
(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.
Solubility
Soluble in chloroform. Slightly soluble in methanol.
Notes
Air sensitive. Incompatible with strong oxidizing agents.
(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.
Solubility
Soluble in chloroform. Slightly soluble in methanol.
Notes
Air sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- Stabilized ylide which converts aldehydes to methyl ɑß-enones (see Appendix 1). Metallation with n-BuLi and alkylation, followed by Wittig reaction with an aldehyde provides a route to ɑß-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(trimethyl silyl) acetamide, L00183.
- Zhang, Y.; Wu, S.; Wang, S.; Fang, K.; Dong, G.; Liu, N.; Miao, Z.; Yao, J.; Li, J.; Zhang, W.; Sheng, C.; Wang, W. Divergent Cascade Construction of Skeletally Diverse Privileged Pyrazole-Derived Molecular Architectures. Eur. J. Org. Chem. 2015, 2015 (9), 2030-2037.
- Chu, S.; Wallace, S.; Smith, M. D. A Cascade Strategy Enables a Total Synthesis of (-)-Gephyrotoxin. Angew. Chem. Int. Ed. 2014, 53 (50), 13826-13829.