22422-16-8

Upstream product

• 19753-68-5 3-Bromo-2-oxopropylidenetriphenylphosphorane 
• 100-52-7 benzaldehyde 
• 73400-25-6 {(1E)-3-[(trimethylsilyl)oxy]buta-1,3-dien-1-yl}benzene 
• 4192-77-2 ethyl cinnamate 
• 74-95-3 1,1-dibromomethane 
• 211996-14-4 acetic acid (E)-1-methylene-3-phenyl-allyl ester 
• 100573-50-0 (E)-4-phenyl-2-(trimethylsiloxy)but-3-enenitrile 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 17157-48-1 bromoacetaldehyde 
• 104516-09-8 1-phenylbuta-2,3-dien-1-ol 
• 80783-99-9 N-methoxy-N-methylcinnamamide 
• 1896-62-4 (E)-benzalacetone 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 78600-92-7 Triphenyl-cinnamoylmethyl-phosphonium 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 112894-69-6 (E)-1-(2,6-Dimethyl-pyran-4-ylidene)-4-phenyl-but-3-en-2-one 
• 69342-62-7 2-(α-hydroxycinnamylidene)-4,5-dimethylcyclopent-4-ene-1,3-dione 
• 78600-80-3 methyl 3-methoxy-8-phenyl-4,6-dioxo-octa-2,7-dienoate 
• 78600-82-5 3,4-Dimethyl-5-[(E)-2-oxo-4-phenyl-but-3-en-(E)-ylidene]-5H-furan-2-one 
• 78600-81-4 Z-4-cinnamoylmethylidene-2,3-dimethylbut-2-en-4-olide 
• 78600-79-0 Z-cinnamoylmethylidene-3-methoxybut-2-en-4-olide 
• 13527-03-2 cinnamoylmethylenetriphenylphosphorane 
• 1338577-19-7 3-O-[(E)-(2-oxo-4-phenylbut-3-en-1-yl)]kaempferol 
• 848312-31-2 (E)-dimethyl 2-(but-2-ynyl)-2-(2-oxo-4-phenylbut-3-enyl)malonate 

Relevant academic research and scientific papers

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

Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions

A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.

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.

Vanadium-Catalyzed Coupling of Allenols with Electrophilic Halide Sources for the Formation of α-Halo-α′,β′-unsaturated Ketones

A vanadium-catalyzed coupling of allenylic alcohols with electrophilic halide sources to form α-halo-α′,β′-unsaturated ketones is described. The process proceeds through a metal enolate formed from the 1,3-transposition of an allenol that is initiated by

Alkoxybromination of olefins using ammonium bromide and oxone

A mild, efficient, and highly regio- and stereoselective method for the methoxy and ethoxy bromination of olefins has been developed using NH 4Br as a bromine source and Oxone as an oxidant. Various kinds of olefins (aromatic, linear, and cyclic olefins) afforded the corresponding alkoxy brominated products in moderate to excellent yields. Taylor & Francis Group, LLC.

FLAVONE DERIVATIVES AND THEIR PREPARATIVE METHOD AND MEDICAL USE

Flavone derivatives, preparative method of the derivatives and use thereof as medicaments for treating diabetes. The structure of the derivatives is presented by formula 1: In the structure, R1 and R2, which are identical or not, represent hydrogen atom, halogen, cyano, hydroxyl, trifluoromethyl, thio-methyl, benzyloxy, C1-C8 linear chain or branch chain alkyl, C1-C8 linear chain or branch chain alkoxy. The pharmacological test indicates that the flavone derivatives can significantly increase the glucose consumption of Hep-G2 cell with insulin resistance activity, promote translocation of glucose transporter 4 of skeletal muscle cells (L6GLUT4myc) at different level, and significantly increase glucose intake and utilization by cells. The test proves the fact for the first time that the flavone derivatives can significantly promote translocation of glucose transporter 4 of skeletal muscle cells, and one of the mechanisms for treating diabetes is activating the cell AMPK phosphorylation and phosphorylating the downstream ACC.

Synthesis of α,β-unsaturated α′-haloketones through the chemoselective addition of halomethyllithiums to Weinreb amides

A straightforward synthesis of variously functionalized α,β-unsaturated α′-haloketones has been achieved through the chemoselective addition of halomethyllithium carbenoids to Weinreb amides at -78 C. A comparative study employing the corresponding esters under the same reaction conditions pointed out that the instability of the tetrahedral intermediate formed from the latter is responsible for the observed formation of carbinols instead of the desired haloketones.

Tungsten(0)- and rhenium(I)-catalyzed tandem cyclization of acetylenic dienol silyl ethers based on geminal carbo-functionalization of alkynes

Tungsten(0)- and rhenium(I)-catalyzed reactions of acetylenic dienol silyl ethers based on the concept of geminal carbo-functionalization of alkynes are reported. Treatment of 3-siloxy-1,3-diene-7-ynes with catalytic amounts of [W(CO)6] or [ReCl(CO)5] under photoirradiation conditions gives synthetically useful bicyclo[3.3.0]octane derivatives in good yields. Extremely high catalytic activity is noted for the rhenium(I) complex. The reaction has been extended to substrates containing a nitrogen atom in their tethers. In this case, two kinds of synthetically useful heterocyclic compounds-the 2-azabicyclo[3.3.0]octane derivatives 9 and the monocyclic dihydropyrroles 10, with allenyl substituents-are obtained, and selective preparation of either product can be achieved through the use of an appropriate combination of the nitrogen substituent and the type of the rhenium(I) catalyst. The 2-azabicyclo[3.3.0]octane derivatives 9 are obtained selectively by carrying out treatment of N-Ns derivatives in the presence of [ReCl(CO) 4(PPh3)], whereas the dihydropyrrole derivatives 10 are obtained by treatment of N-Mbs derivatives with [ReCl(CO)5]/ AgSbF6. Finally, we have applied this geminal carbo-functionalization to one-carbon-elongated substrates containing N-Ts moieties in their tethers. Selective 5-exo cyclization is achieved in the presence of gold(I) or rhenium(I) catalysts, whereas 6-endo cyclization is observed on use of [W(CO) 6]. Geminal carbo-functionalization of 3-siloxy-1,3-dien-7-ynes leading to bicyclo[3.3.0]octane derivatives is achieved through electrophilic activation of alkynes by tungsten(0) and rhenium(I) catalysts (see graphic). Extremely high activity is noted for rhenium(I) catalysts. Furthermore, selective preparation of two different classes of heterocyclic compounds from 5-aza-3-siloxy-1,3-dien-7-ynes is also achieved by appropriate choice of the rhenium(I) catalyst and the protecting group on the nitrogen. Copyright

Synthesis and biological activity of novel tiliroside derivants

A series of new tiliroside derivatives were synthesized and characterized by analytical 1H NMR, 13C NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5′-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes.

Synthetic studies on and mechanistic insight into [W(CO) 5(L)]-catalyzed stereoselective construction of functionalized bicyclo[5.3.0]decane frameworks

Stereoselective preparation of a variety of synthetically useful functionalized bicyclo[5.3.0]decane derivatives was achieved by tandem cyclization of 3-siloxy-1,3,9-triene-7-yne derivatives based on the electrophilic activation of alkynes catalyzed by [W(CO)5(L)], The reaction proceeded smoothly under photoirradiation, and various substrates were cyclized to give the corresponding bicyclic compounds with up to four chiral centers stereospecifically. Reactions of siloxydienes with a silyl substituent as an equivalent of a hydroxyl group also proceeded with wide generality to afford silyl-substituted bicyclo[5.3.0]decanes, which were highly useful as synthetic intermediates. Stereochemical studies concerning the silyl enol ether moiety suggested that two types of reaction path way for the formation of seven-membered rings were present. The reaction of (Z)-enol silyl ethers proceeded through Cope rearrangement of cis-divinylcyclopropane intermediates, and that of (E)-enol silyl ethers by 1,4-addition of the dienyl tungsten species at the position δ to the metal atom. In the reactions of siloxydiene derivatives with silyl substituents, all possible diastereomers could be synthesized stereoselectively by changing the geometry of the silyl enol ether and enyne moieties.