98749-52-1

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 19493-09-5 Methylenetriphenylphosphorane 
• 6048-14-2 [2-oxo-4-phenyl-(3E)-butenyl]triphenylphosphonium bromide 
• 22422-16-8 α-bromomethyl styryl cetone 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 22422-16-8 (E)-1-bromo-4-phenylbut-3-en-2-one 
• 603-35-0 triphenylphosphine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 64448-06-2 (N-phenyliminovinylidene)triphenylphosphorane 
• 1896-62-4 (E)-benzalacetone 
• 98749-42-9 N-<(E)-Cinnamoyl>-2-(triphenylphosphoranyliden)acetanilid 

Downstream Products

• 923025-67-6 (5Z)-3,4-dimethyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2(5H)-one 
• 923025-68-7 (5E)-5-[(E)-2-oxo-4-phenylbut-3-enylidene]-3-phenylfuran-2(5H)-one 
• 730971-73-0 2-[(E)-1-hydroxy-3-phenylallylidene]-4-methylcyclopent-4-ene-1,3-dione 
• 923025-74-5 2-(1-hydroxy-3-phenyl-allylidene)-4,5-dimethyl-cyclopent-4-ene-1,3-dione 
• 923025-66-5 (5E)-3-methyl-5-[(E)-2-oxo-4-phenylbut-3-enylidene]furan-2(5H)-one 
• 1608-03-3 (E)-but-1-en-3-yn-1-ylbenzene 
• 935-01-3 (Z)-1-phenylbuten-3-yne 
• 791-28-6 Triphenylphosphine oxide 

Relevant academic research and scientific papers

N-Heterocyclic Carbene Catalyzed (5+1) Annulations Exploiting a Vinyl Dianion Synthon Strategy

Direct polarity inversion of conjugate acceptors provides a valuable entry to homoenolates. N-heterocyclic carbene (NHC) catalyzed reactions, in which β-unsubstituted conjugate acceptors undergo homoenolate formation and C?C bond formation twice, have been developed. Specifically, the all-carbon (5+1) annulations give a range of mono- and bicyclic cyclohexanones (31 examples). In the first family of annulations, β-unsubstituted acrylates tethered to a divinyl ketone undergo cycloisomerization, providing hexahydroindenes and tetralins. In the second, partially untethered substrates undergo an intermolecular (5+1) annulation involving dimerization followed by cycloisomerization. While enantioselectivity was not possible with the former, the latter proved viable, allowing cyclohexanones to be produced with high levels of enantiopurity (most >95:5 e.r.) and exclusive diastereoselectivity (>20:1 d.r.). Derivatizations and mechanistic studies are also reported.

Synthesis, antifungal activity, and structure-activity relationships of coruscanone A analogues

Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.

Novel cyclopentenedione antifungal compounds and methods for their use

Compounds and methods useful in the control, treatment, and prevention of fungal activity, of the following formula: where R1-3 are independently H, alkyl, methyl, acyl, halogen, phenyl, R4 is H, alkyl, methyl, acyl, alkoxy, halogen,

Antifungal cyclopentenediones from Piper coruscans

Coruscanones A and B, two new antifungal cyclopentenedione derivatives, have been isolated from Piper coruscans and their structures elucidated by spectroscopic and chemical methods. Coruscanone A exhibits significant antifungal activity against Candida a

Flash Vacuum Pyrolysis of Stabilised Phosphorous Ylides. Part 6. Pyrolysis of Substituted Cinnamoyl Ylides as a Route to Conjugated Enynes

The substituted cinnamoyl ylides 6 and 7, readily prepared in one step from the quaternary phosphonium salts 8 and cinnamoyl chlorides 9, undergo extrusion of Ph3PO upon FVP to give the 1,3-enynes 12 and 13 in moderate yield.At 500 deg C there is little double bond isomerisation, but at 700 deg C this does occur to give almost 1:1 mixtures of E and Z isomers.In a few cases, including those with a nitrophenyl group present, the yields are poor or the reactions fail stabilised ylide was only partly successful since the severe conditions required for loss of the ester group resulted in significant isomerisation to naphthalene.The fully assigned 13C NMR spectra for 20 enynes are reported.One examples of the isomeric β,γ-unsaturated-δ-oxo ylides, 14 has been prepared and is found to undergo loss of Ph3P on FVP at 700 deg C to give indene and benzene in low yield.

Cumulated Ylides, XVI. A Method for the Exchange of the OH Group in Free Carboxylic Acids by the Ylide Function

Carboxylic acids 5 react with triphenylphosphorane (4) via the intermediate 6 with formation of the phosphoranes 7, which rearrange by heating in an intramolecular acyl migration to ylides 10.By heating of 10 in the presence of an alcohol 13 the acyl ylides 11 and urethanes 14 are formed.The reaction sequence allows the replacement of the OH group in carboxylic acids by the ylide function.