131292-14-3

Upstream product

• 51718-85-5 ethyl 3-(4-methoxyphenyl)propynoate 
• 100-66-3 methoxybenzene 
• 7515-17-5 methyl 3-(4-methoxyphenyl)propynoate 
• 157019-58-4 2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 

Downstream Products

• 101880-50-6 1-(4-methoxy-phenyl)-naphthalene-2,3-dicarboxylic acid-anhydride 
• 101880-51-7 7-methoxy-1-phenyl-naphthalene-2,3-dicarboxylic acid-anhydride 
• 97746-16-2 5,7-dihydroxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one 
• 428864-81-7 2,4,6-trimethylphenyl 3-(4-methoxyphenyl)prop-2-ynoate 
• 7642-31-1 1-(4-methoxyphenyl)-1,3-butadiyne 
• 1042036-34-9 3-(4-methoxyphenyl)propynoic acid benzylisopropenylamide 
• 79229-97-3 N-benzyl-3-(p-methoxyphenyl)propynamide 
• 1207847-91-3 1-[3-(4-methoxyphenyl)propynoyl]-1,2,3,4,5,6-hexahydro[1]pyrindine-4a-carboxylic acid ethyl ester 
• 131292-07-4 ethyl 5-(4-methoxyphenyl)-3-oxo-2-triphenylphosphoranylidenepent-4-ynoate 
• 1187591-01-0 C₃₈H₃₄N₂O₆ 
• 1227841-06-6 (E)-benzaldehyde O-3-(4-methoxyphenyl)propioloyl oxime 
• 109034-41-5 2-(4-methoxyphenyl)-6-phenyltellura-4H-pyran-4-one 

Relevant academic research and scientific papers

Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction

The extensively developed ene-type enantioselective cycloisomerization of classical 1,n-enynes provides an efficient approach to chiral cyclic 1,4-dienes. In contrast, the catalytic asymmetric heteroarenyne (heteroarene–alkyne) cycloisomerization involving the dearomative transformation of endocyclic aromatic C=C bonds remains unknown. Herein, we communicate a PdH-catalyzed enantioselective heteroarenyne cycloisomerization reaction of alkyne-tethered indole substrates (formal 1,5- and 1,6-enynes). Based on this strategy, a variety of structurally diverse chiral spiro and fused indoline derivatives bearing quaternary stereocenters and exocyclic C=C bonds are afforded in moderate to excellent yields and excellent enantioselectivities (up to 98 % ee). The classical ene-type enantioselective 1,5-enyne cycloisomerization of N-vinylpropiolamides is also developed to afford chiral 2-pyrrolones in good to excellent ee values.

Asymmetric Catalysis in Liquid Confinement: Probing the Performance of Novel Chiral Rhodium–Diene Complexes in Microemulsions and Conventional Solvents

The role of liquid confinement on the asymmetric Rh catalysis was studied using the 1,2-addition of phenylboroxine (2) to N-tosylimine 1 in the presence of [RhCl(C2H4)2]2 and chiral diene ligands as benchmark reaction. To get access to Rh complexes of different polarity, enantiomerically pure C2-symmetric p-substituted 3,6-diphenylbicyclo[3.3.0]octadienes 4 and diastereomerically enriched unsymmetric norbornadienes 5 and 6 carrying either the Evans or the SuperQuat auxiliary were synthesized. A microemulsion containing the equal amounts of H2O/KOH and toluene/reactants was formulated using the hydrophilic sugar surfactant n-octyl β-d-glucopyranoside (C8G1) to mediate the miscibility between the nonpolar reactants and KOH, needed to activate the Rh–diene complex. Prominent features of this organized reaction medium are its temperature insensitivity as well as the presence of water and toluene-rich compartments with a domain size of 55 ? confirmed by small-angle X-ray scattering (SAXS). Although bicyclooctadiene ligands 4 a,b,e performed equally well under homogeneous and microemulsion conditions, ligands 4 c,d gave a different chemoselectivity. For norbornadienes 5, 6, however, microemulsions markedly improved conversion and enantioselectivity as well as reaction rate, as was confirmed by kinetic studies using ligand 5 b.

Gold-catalyzed cyclization and subsequent arylidene group transfer of O-propioloyl oximes

Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 °C in the presence of Au(PPh3)NTf2 (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.

A new route to tricyclic 2-pyridone frameworks via formation of bicyclic N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization

A cationic gold(I)/PPh3 complex catalyzes cycloisomerizations of bicyclic N-alkenyl alkynylamides leading to tricyclic 2-pyridone derivatives at room temperature in good yields. The bicyclic N-alkenyl alkynylamides are readily prepared starting from commercially available 2-substituted cycloalkanones.

Synthesis-driven mapping of the dictyodendrin alkaloids

The dictyodendrin alkaloids have been described as the first telomerase inhibitors of marine origin. As such they represent interesting lead compounds in the quest for small molecule inhibitors of this tumor-marker enzyme. Described herein is the preparat

Convergent and rapid assembly of substituted 2-pyridones through formation of N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization

(Chemical Equation Presented) A new method for the convergent and rapid assembly of substituted 2-pyridones was developed through the formation of N-alkenyl alkynylamides (amide-linked 1,5-enynes) by N-acylation of !mines with alkynoyl chlorides and the subsequent cationic Au(l)/PPh3-catalyzed cycloisomerization.

An efficient synthesis of neoflavonoid antioxidants based on Montmorillonite K-10 catalysis

A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.

Unexpected thermal transformation of aryl 3-arylprop-2-ynoates: Formation of 3-(diarylmethylidene)-2,3-dihydrofuran-2-ones

A number of aryl 3-arylprop-2-ynoates 3 has been prepared (cf. Table 1 and Schemes 3-5). In contrast to aryl prop-2-ynoates and but-2-ynoates, 3-arylprop-2-ynoates 3 (with the exception of 3b) do not undergo, by flash vacuum pyrolysis (FVP), rearrangement to corresponding cyclohepta[b]furan-2(2H)-ones 2 (cf. Schemes 1 and 2). On melting, however, or in solution at temperatures >150% the compounds 3 are converted stereospecifically to the dimers 3-[(Z)-diarylmethylidene]-2,3-dihydrofuran-2-ones (Z)-11 and the cyclic anhydrides 12 of 1,4-diarylnaphthalene-2,3-dicarboxylic acids, which also represent dimers of 3, formed by loss of one molecule of the corresponding phenol from the aryloxy part (cf. Scheme 6). Small amounts of diaryl naphthalene-2,3-dicarboxylates 13 accompanied the product types (Z)-11 and 12, when the thermal transformation of 3 was performed in the molten state or at high concentration of 3 in solution (cf. Tables 2 and 4). The structure of the dihydrofuranone (Z)-11c was established by an X-ray crystal-structure analysis (Fig. 1). The structures of the dihydrofuranones 11 and the cyclic anhydrides 12 indicate that the 3-arylprop-2-ynoates 3, on heating, must undergo an aryl O → C(3) migration leading to a reactive intermediate, which attacks a second molecule of 3, finally under formation of (Z)-11 or 12. Formation of the diaryl dicarboxylates 13, on the other hand, are the result of the well-known thermal Diels-Alder-type dimerization of 3 without rearrangement (cf. Scheme 7). At low concentration of 3 in decalin, the decrease of 3 follows up to ca. 20% conversion first-order kinetics (cf. Table 5), which is in agreement with a monomolecular rearrangement of 3. Moreover, heating the highly reactive 2,4,6-trimethylphenyl 3-(4-nitrophenyl)prop-2-ynonate (3f) in the presence of a twofold molar amount of the much less reactive phenyl 3-(4-nitrophenyl)prop-2-ynonate (3g) led, beside (Z)-11f, to the cross products (Z)-11fg, and, due to subsequent thermal isomerization, (E)-11fg (cf. Scheme 10), the structures of which indicated that they were composed, as expected, of rearranged 3f and structurally unaltered 3g. Finally, thermal transposition of [17O]-3i with the 17O-label at the aryloxy group gave (Z)- and (E)-[17O2]-11i with the 17O-label of rearranged [17O]-3i specifically at the oxo group of the two isomeric dihydrofuranones (cf. Scheme 8), indicating a highly ordered cyclic transition state of the aryl O → C(3) migration (cf. Scheme 9).

2,5-diarylisothiazolone: Novel inhibitors of cytokine-induced cartilage destruction

A series of 2,5-diarylisothiazolones is reported that inhibit the IL-1β- induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, n

Flash Vacuum Pyrolysis of Stabilised Phosphorous Ylides. Part 4. Stepwise Construction of Terminal 1,3-Diynes, Conjugated Diacetylenic Esters and a Triacetylenic Ester

Thirteen examples of stabilised alkynol ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 deg C, to undergo extrusion of Ph3PO to give the diacetylenic esters 7 in moderate yield.At 750 deg C the same ylides afforded terminal 1,3-diynes 8 although often in poor yield.For R = 2-MeSC6H4 both 7 and 8 undergo secondary loss of Me* and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield.The first example of an alkadiynol ylide 11 has been prepared and is converted by FVP at 500 deg C into the triacetylenic ester 12.