24720-64-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(TRIPHENYLPHOSPHORANYLIDENE)PROPIONALDEHYDE is used as a reactant for the preparation of acitretin analogs with antitumor activity. These analogs have the potential to be developed into new cancer treatments, offering hope for patients with various types of cancer.
Used in Organic Chemistry:
2-(TRIPHENYLPHOSPHORANYLIDENE)PROPIONALDEHYDE is used as a reagent in the stereoselective synthesis of essential building blocks of phorboxazole A via hetero Diels-Alder and stereoselective hetero-Michael addition/equilibration. This process allows for the creation of complex molecular structures with high levels of stereoselectivity, which is crucial in the development of new pharmaceuticals and other chemical compounds.
Used in Natural Product Synthesis:
2-(TRIPHENYLPHOSPHORANYLIDENE)PROPIONALDEHYDE is used as a reagent in the preparation of the C1-C14 fragment of sarcoglaucol-16-one via Z-selective ando-type Horner-Wadsworth-Emmons olefination. This process is essential in the synthesis of natural products, which often have unique and valuable biological properties.
Used in Wittig Reactions:
2-(TRIPHENYLPHOSPHORANYLIDENE)PROPIONALDEHYDE is used as a reagent in Wittig reactions, which are widely used in organic chemistry for the synthesis of alkenes. These reactions are particularly useful in the creation of complex molecular structures with specific geometries, which can be important in the development of new pharmaceuticals and other chemical compounds.
Used in Apoptosis-Inducing Agents:
2-(TRIPHENYLPHOSPHORANYLIDENE)PROPIONALDEHYDE is used as a reagent in the synthesis of ring-expanded and epothilone-hybridized macrosphelide analogs as apoptosis-inducing agents. These compounds have the potential to be developed into new treatments for various diseases, including cancer.
Used in Inhibitors of IMPDH:
2-(TRIPHENYLPHOSPHORANYLIDENE)PROPIONALDEHYDE is used as a reagent in the preparation of phosphonic acid-containing analogs of mycophenolic acid as inhibitors of IMPDH (inosine monophosphate dehydrogenase). These inhibitors can be used in the development of new treatments for autoimmune diseases and other conditions.

InChI:InChI=1/C21H19OP/c1-18(17-22)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

Upstream product

• 1530-32-1 ethyltriphenylphosphonium bromide 
• 109-94-4 formic acid ethyl ester 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 10349-38-9 p-methoxyphenylisonitrile 
• 90601-11-9 <2-(dimethylamino)vinyl>triphenylphosphonium chloride 
• 82248-14-4 <2-(Dimethylamino)vinyliden>triphenylphosphoran 
• 90601-12-0 <2-(Dimethylamino)-1-methylvinyl>triphenylphosphonium-chlorid 

Downstream Products

• 171826-88-3 (E)-2-methyl-4-(2-hydroxy-1-(methoxycarbonyl)-4-methoxy-3-phenyl)-2-butenal 
• 171826-89-4 (E)-2-methyl-4-(2-hydroxy-1-(methoxycarbonyl)-4-methoxy-5-methyl-3-phenyl)-2-butenal 
• 171826-90-7 (E)-2-methyl-4-(5-chloro-2-hydroxy-1-(methoxycarbonyl)-4-methoxy-3-phenyl)-2-butenal 
• 101376-74-3 (E)-4-(benzyloxy)-2-methylbut-2-enal 
• 596109-36-3 9-(tert-butyldiphenylsilanyloxy)-2-methylnona-2,7-dienal 
• 749924-32-1 (E)-3-[(Z)-(2R,8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-2-methyl-propenal 
• 373392-37-1 (1'R,2'S,5'R)-8'-phenylmenthyl (2Z,4S,7E)-4-formyloxy-8-methyl-9-oxo-2,7-nonadienoate 
• 897049-94-4 (5R,6S)-5,6-Dimethyl-6-((E)-3-methyl-4-oxo-but-2-enyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 912542-38-2 (2E,4E)-5-[(5S,6S,9S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-6,9-dimethyl-2-oxo-1-oxa-spiro[4.5]deca-3,7-dien-6-yl]-2-methyl-penta-2,4-dienal 
• 95532-05-1 (E)-5-Benzyloxy-2-methyl-pent-2-enal 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 62054-49-3 ethyl (E)-3-formyl-2-butenoate 
• 139630-91-4 (E)-2-methyl-3-(2-methyloxazol-4-yl)acrylaldehyde 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 

Relevant academic research and scientific papers

THE VINYLOGATION OF ALDEHYDES: AN IMPROVED METHOD FOR THE PREPARATION OF ALPHA FORMYLETHYLIDENETRIPHENYLPHOSPHORANE, AND AN IMPROVED ALPHA SILYL IMINE REAGENT OF PROPIONALDEHYDE

A high yield preparation of α-formylethylidenetriphenylphosphorane from the ethyltriphenylphosphonium iodide and ethyl formate is reported.The α-triethylsilyl t-butylimine of propionaldehyde is thermally stable and easily purified reagent that smoothly ol

Preparation and characterization of PdII-ylide complexes of type 3-2-XC3H4)>BF4 (X=H, Me; R=p-C6H4OMe, C(Me)3, Me, C6H11, p-c6H4NO2). Crystal structure of (η3-2-MeC3H4)>BF4

Seven compounds of general formula 3-2-XC3H4)>BF4 (X=H, R=p-C6H4OMe (1), R=C(Me)3 (2); X=Me, R=p-C6H4OMe (3), C(Me)3 (4), Me (5), C6H11 (6), p-C6H4NO2 (7)) have been prepared by chloride abstraction from PdCl(η3-2-XC3H4) (X=H, Me) with AgBF4 and subsequent reaction of the cationic intermediate with the appropriate isocyanide ligand.All the complexes have been characterized by analitical and spectroscopic (IR, 1H and 31P NMR) data.They have been shown to be mixture of two diastereoisomeric forms arising from the simultaneous presence on the palladium atom of the asymmetric ylidic carbon atom and the η3-allyl ligand.The determination of the crystal structure of complex 4 showed that in the solid state only diastereoisomer is present.The crystals are monoclinic, space group Pc with a 9.833(3), b 14.383(4), c 11.762(4) Angstroem, β 114.68(3) deg, and Z=2.Final full-matrix least-squares refinement, based on 2413 reflections, convergated to R=0.050.The keto-stabilized ylide ligand is C bonded to the metal with a Pd-C distance of 2.175(9) Angstroem.

A Study Directed to the Asymmetric Synthesis of the Antineoplastic Macrolide Acutiphycin under Enantioselective Acyclic Stereoselection Based on Chiral Oxazaborolidinone-Promoted Asymmetic Aldol Reactions

A shortening of the reaction path can be realized by using a series of the chiral oxazaborolidinone-promoted aldol reaction with respect to the practical synthesis of the (+)-acutiphycin seco acid derivative 5. The linear strategy is based on the utilizat

Reaction of Oxygen Nucleophiles With β-Alkoxyvinylphosphonium Salts. Isolation of Phosphine Oxides.

A variety of β-alkoxyvinylphosphonium bromides were prepared and reacted with sodium ethoxide and dimsyl anion to generate good yields of phosphine oxides 3 rather than the previously reported ylide 4.

Reactions with Phosphine Alkylenes, XLV. Reactions of Alkylidenetriphenylphosphoranes with Tetramethylformamidinium Chloride. Synthesis of triphenylphosphonium Chloride and (Formylalkylidene)triphenylphosphoranes

Phosphonium ylides 1 react with tetramethylformamidinium chloride (2) to form enamine phosphonium chlorides 8 and the formic orthoamide 7.The salts 8 show temperature depending 1H NMR spectra with respect to the protons of the dimethylamino group (hindered rotation around the C - N(CH3)2 bond).Treatment of 8 with acids and subsequently with bases gives rise to the formation of the formyl ylides 19. 8a is deprotonated with sodium amide to give the phosphaallene ylide 20, which reacts with water to yield the phosphane oxide 21, and with methyl iodide stereospecifically to form 8b.