1838-44-4Relevant academic research and scientific papers
Synthesis of 1,1-diarylethylenes
Chang, Meng-Yang,Huang, Yi-Hsuan,Wang, Heui-Sin
, p. 3022 - 3031 (2016/05/19)
A facile route toward 1,1-diarylethylenes 6 has been developed in good yields via mCPBA-promoted oxidation of β-hydroxysulfides 2, BF3·OEt2-mediated Friedel-Crafts reaction of the resulting β-hydroxysulfoxides 3 with oxygenated benze
Synthesis of 2-phenylbenzofuran derivatives and selective binding activities on estrogen receptor
Zhang, Ping,Yang, Yewei,Zheng, Xiaoliang,Huang, Wenhai,Ma, Zhen,Shen, Zhengrong
, p. 270 - 274 (2012/03/11)
An improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a-g and the intermediate diols 4a-g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vitro. Among these fourteen tested compounds, 4g and 5g showed higher binding affinity on ER subtypes, ERα and ERβ. Compound 4g exhibited preferable ERα binding, while 5g was more estrogen selective for ERβ. The molecular docking was also performed to explore the detailed interactive interface between ER and the compounds.
2-substituted benzo[b]furans from (E)-1,2-dichlorovinyl ethers and organoboron reagents: Scope and mechanistic investigations into the one-pot Suzuki coupling/direct arylation
Geary, Laina M.,Hultin, Philip G.
supporting information; experimental part, p. 5563 - 5573 (2010/12/29)
2-Substituted benzo[b]furans can easily be assembled from simple phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid synthesis of many analogues using essentially the same chemistry, of particular value in drug development. Results of kinetic isotope effect studies and investigations into the regioselectivity of the process indicate that the direct arylation step most likely does not involve an electrophilic palladation. The most likely mechanism lies somewhere on the continuum between a C-H bond metathesis and an assisted palladation or concerted metallation-deprotonation pathway. A very efficient modular approach to the construction of benzo[b]furans using trichloroethylene as a scaffold is described. This method gives easy access to highlysubstituted heterocycles in only two synthetic operations, and is especially suitable for rapid construction of compound libraries.
Modular construction of 2-substituted benzo[b]furans from 1,2-Dichlorovinyl ethers
Geary, Laina M.,Hultin, Philip G.
supporting information; experimental part, p. 5478 - 5481 (2010/02/27)
"Chemical Equation Presented" (E)-1,2-Dichlorovinyl ethers and amides are easily accessible from trichloroethylene via nucleophilic addition across in situ synthesized dlchloroacetylene. A one-pot, sequential Suzukl-Miyaura coupling/intramolecular direct
Benzofuran compounds, compositions, and methods
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, (2008/06/13)
The present invention provides novel compound of the formula: wherein Rais —OH or —O—(C1-C4alkyl); R1ais —OH or —O—(C1-C4alkyl); n is 2 or 3; R2and R3are each independ
Structure-activity relationship of antiestrogens: A study using triarylbutenone, benzofuran, and triarylfuran analogues as models for triarylethylenes and triarylpropenones
Durani,Jain,Saeed,Dikshit,Durani,Kapil
, p. 1700 - 1707 (2007/10/02)
In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constra
The Oxidation of (E)-α-Phenylcinnamic Acids with Manganese(III) Acetate
Oishi, Kazuki,Kurosawa, Kazu
, p. 179 - 184 (2007/10/02)
The oxidation of eight (E)-α-phenylcinnamic acids with manganese(III) acetate in boiling acetic acid containing acetic anhydride gave 3-phenylcoumarins, 3-phenyl-1-oxaspirodeca-3,7,9-triene-2,6-diones, 2-phenylbenzofurans, 3-(acetoxymethyl)-2-phenylbenzofurans, 3-formyl-2-phenylbenzofuran, 2-acetoxy-2-phenyl-3(2H)-benzofuranones, (Z)-Α-acetoxystilbenes, 2-acetoxy-1,2-diphenylethanones, 5-acetoxy-4,5-diphenyl-2(5H)-furanones, and diphenylacetylene.Tha reaction pathways are discussed.
