119460-70-7

Upstream product

• 119460-71-8 (Z)-3-benzylidene-3H-benzofuran-2-one 
• 553-86-6 benzofuran-2(3H)-one 
• 100-52-7 benzaldehyde 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 865082-24-2 2-iodophenyl propiolate 
• 98-80-6 phenylboronic acid 
• 1115095-78-7 (Z)-2-(2-methoxymethoxyphenyl)-3-phenylacrylic acid 
• 4279-76-9 phenoxyacetylene 
• 201024-81-9 C,N-diphenylnitrone 
• 73406-74-3 3-benzyl-3H-benzofuran-2-one 
• 91-47-4 2,3-diphenylacrylic acid 
• 119460-67-2 Z-2-(o-methoxyphenyl)-3-phenyl propenoic acid 
• 93435-11-1 2-hydroxy-2-(2-methoxy-phenyl)-3-phenyl-propionic acid 
• 1657-65-4 (E)-2-(2-methoxyphenyl)-3-phenylpropenoic acid 

Downstream Products

• 1262424-35-0 C₂₅H₂₀O₃ 
• 119460-71-8 (Z)-3-benzylidene-3H-benzofuran-2-one 
• 1262424-27-0 C₂₇H₂₂O₃ 

Relevant academic research and scientific papers

Inhibitory activities against topoisomerase I and II by isoaurostatin derivatives and their structure-activity relationships

Isoaurostatin A (IAS-A) isolated from Thermomonospora alba showed weak inhibition against topoisomerase (topo) I (IC50 = 307 μM). To get more strong inhibition, derivatives of IAS-A were prepared and their structure-activity relationships against topo I and II were investigated. The addition of hydroxyl group on aromatic rings increased the activities, 3-(3,4,5-trihydroxybenzylidene)-5-hydroxy-3H-benzofuran-2-one (IAS-9) showed strong inhibition (IC50 = 3 μM) against topo I. And also, the increasing of hydroxyl group increased growth inhibition against a variety of cancer cells, and IAS-9 showed most potent inhibition. Unlike camptothecin and etoposide, IAS-9 neither stabilized DNA-topo cleavable complex nor intercalated into DNA, and it inhibited topo I and II noncompetitively. The inhibitory activities also increased by opening of lactone ring in the molecule of IAS-9.

P-Spiro phosphonium salts catalyzed asymmetric fluorination of 3-substituted benzofuran-2(3H)-ones

Abstract Asymmetric electrophilic fluorination of 3-substituted benzofuran-2(3H)-ones was realized under liquid-liquid phase-transfer catalysis with 2 mol% of chiral phosphonium salts to afford the fluorinated products with up to 96% yield and 56% ee.

A new and efficient synthesis of pyridazin-3(2H)-ones via 1,3-dipolar cycloaddition

3-Arylidenebenzofuran-2(3H)-ones are obtained by condensation of aldehydes Ar1CHO with benzofuran-2(3H)-one. A mixture of stereoisomers (Z) and (E) was isolated. The reaction of diarylnitrilimines with the Z+E mixture or with each stereoisomer leads regio- and and stereoselectively to cycloadducts which give, after acidic treatment, the same 5,6-diaryl-4-(0-hydroxyphenyl)pyridazin-3(2H)-one 6, irrespective of the double bond geometry of the starting olefin.

Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity

The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.

Pd(II)-catalyzed enantioselective C-H activation/C-O bond formation: Synthesis of chiral benzofuranones

Pd(II)-catalyzed enantioselective C-H activation of phenylacetic acids followed by an intramolecular C-O bond formation afforded chiral benzofuranones. This reaction provides the first example of enantioselecctive C-H functionalizations through Pd(II)/Pd(IV) redox catalysis.

Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions

We have developed efficient catalytic methods for the stereoselective and diversity synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles and 3-alkylidene-benzofuran-2-ones via palladium-catalyzed Heck/Suzuki-Miyaura, Heck/Heck, and Hec

ALKYL (E)- AND (Z)-2,3-DIBROMOPROPENOATES AS PRECURSORS TO 3-SUBSTITUTED ALKYL (E)- AND (Z)-2-BROMOPROPENOATES, 2,3-DISUBSTITUTED ALKYL (Z)- AND (E)-PROPENOATES AND SOME HETEROCYCLIC COMPOUNDS

3-(1-alkynyl)- and 3-aryl-substituted alkyl (Z)- and (E)-2-bromopropenoates have been stereospecifically and regioselectively synthesized by Pd-catalyzed cross-coupling reactions between 1-alkynylzinc chlorides, arylzinc chlorides or aryltributylstannanes and alkyl (Z)- and (E)-2,3-dibromopropenoates, (Z)- and (E)-2, respectively.The catalyst precursor consisting of a mixture of Pd on carbon and 3.9 equivalents of AsPh3 as well as that obtained by treatment of Pd(OAc)2 with 4 equivalents of AsPh3 in THF at 60 deg C can conveniently replace Pd(PPh3)4 in the reactions between (Z)- or (E)-2 and aryl or 1-alkynylzinc halides.On the other hand, a representative alkyl (Z)-3-alkyl-2-bromopropenoate has been prepared by reaction of a 9-alkyl-9-BBN derivative with (Z)-2a in DMF solution, in the presence of K2CO3 and a catalytic quantity of PdCl2(dppf).Some applications demonstrate the synthetic utility of 3-aryl-substituted alkyl (Z)- and (E)-propenoates, (Z)- and (E)-4.Thus, ethyl (E)-2-bromo-3-propenoate, (E)-4e, represents a direct precursor to 3-bromocoumarin, 7, and compound (Z)-8, which is obtained by acidic hydrolysis of (Z)-4e, undergoes a Pd-catalyzed intramolecular carbonylation reaction, which affords 3-ethoxycarbonylcoumarin, 9, in high yield.Moreover, treatment of compounds (Z)- and (E)-4 with organozinc or organotin derivatives, in the presence of catalytic amounts of a suitable Pd catalyst, affords, stereospecifically and in satisfactory to excellent yields, trisubstituted α,β-unsaturated esters, (E)- and (Z)-10, respectively, which cannot be easily prepared in stereoisomerically pure form by classical procedures.One of these esters, i.e. compound (E)-10c, represents a direct precursor to an isoaurone, i.e. (E)-3- benzylidenebenzofuran-2-one, (E)-11.Finally, a representative stereodefined unsymmetrically 2,3-diaryl-disubstituted alkyl propenoate has been synthesized by a one-pot procedure involving two sequential palladium-catalyzed arylations of (Z)-2a.

ACID CATALYZED ISOMERIZATION OF Z-α-PHENYLCINNAMIC ACIDS AND THEIR CONVERSION TO ISOMERIC ISOAURONES

E(4') and Z(4)-α-phenylcinnamic acids were synthesized.These were been converted into isoaurones.The stereochemistry of these were determined by 1H NMR and Lanthanide induced shift (LIS) studies.