Heterocyclic Building Block-benzofuran

Bohn, Irene published the artcileThe essential root oil of Pimpinella major, Synthetic Route of 13391-27-0, the main research area is Pimpinella root oil composition; sesquiterpene Pimpinella root oil.

The composition of essential oil of P. major roots from 2 different sources in Italy was analyzed and shown to contain trans-epoxypseudoisoeugenyl tiglate as the major constituent (37.34 and 19.54%) along with such minor constituents as pseudoisoeugenyl tiglate and epoxypseudoisoeugenyl 2-methylbutyrate. Other sesqui- and trinorsesquiterpenoids (C12 hydrocarbons) were present in appreciable amounts, while monoterpenoids were found only in traces. The typical oil composition enables the delimitation of this plant from several other European Pimpinella species and is a valuable tool for evaluating the com. drug Radix pimpinellae. The detection of germacrene C is significant because this is the 1st report of its occurrence in the oil of an umbelliferous plant.

Planta Medica published new progress about Aldehydes. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Synthetic Route of 13391-27-0.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Kayser, Margaret M. published the artcileThe internal steric push-effect: its consequences on the reactivity of carbonyl functions in 3-substituted phthalic anhydrides, Recommanded Product: 4-Chlorophthalide, the main research area is NMR phthalic anhydride; regioselectivity nucleophilic addition; mol mechanic phthalic anhydride.

The 13C NMR for a number of 3-substituted phthalic anhydrides and corresponding lactones were measured. Substituent effects were discussed. MM2 calculations for several 3-substituted phthalic anhydrides predict that the substituent and the neighboring carbonyl group remain coplanar and within the plane of the aromatic ring. To alleviate the imposed crowding, there is an in-plane distortion of the bond angle of the substituent and the carbonyl function. The observed angle of distortion increases with increasing steric demand of the substituent, in agreement with repulsive van der Waals interaction between those two groups. Diminished reactivity of the ortho carbonyl groups vis-a-vis nucleophiles in 3-substituted phthalic anhydrides may be linked to the internal steric push-effect which causes the displacement of electrons in the CO bond from O to C.

Spectroscopy Letters published new progress about Bond angle. 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Recommanded Product: 4-Chlorophthalide.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Pan, Yu-Liang published the artcileEnantioselective Allylation of Oxocarbenium Ions Catalyzed by Bi(OAc)3/Chiral Phosphoric Acid, Quality Control of 52010-22-7, the main research area is alkenylborate hydroxyisobenzofuranone allylation bismuth chiral phosphoric acid; allylisobenzofuranone enantioselective preparation; bismuth chiral phosphoric acid enantioselective allylation catalyst.

Phthalides as the crucial core skeletons are found extensively in natural products and biol. active mols. Disclosed an asym. allylation of 3-hydroxyisobenzofuran-1(3H)-ones with boron allylation reagents to construct chiral phthalide derivatives The simple Bi(OAc)3/chiral phosphoric acid catalytic system proves to be efficient in this method, delivering the desired chiral 3-allylisobenzofuran-1(3H)-ones in good yields (up to 99%) and high enantioselectivities (up to 99.5:0.5 e.r.) under mild conditions. The large-scale reaction and diverse transformations of products to various scaffolds with potential biol. activities render it more attractive. Moreover, the mechanism was preliminarily explored by control reactions, mass spectrometry, deuterium experiment, and DFT calculations

ACS Catalysis published new progress about Allylation. 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Quality Control of 52010-22-7.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ota, Tomomi published the artcileSelective preparation and cyclization of 2-(2-hydroxyphenyl)-2-(isopropylthio)ethanols. New Synthesis of 1-benzofurans, Product Details of C10H10O2, the main research area is benzofuran; acetoxyisopropylthioethylphenol regioselective preparation cyclization; phenol alkylation isopropylthioethyl acetate.

Reaction of 2,4-R(R1)C6H3OH (R = H, R1 = H, Ph, Me, MeO, Cl, cyclohexyl, etc.; R = Me, MeO, Cl, R1 = H) with Me2CHSCH2CH2OMe activated by SO2Cl2 afforded 2-[2-acetoxy-1-(isopropylthio)ethyl]phenols I (R, R1 = as above) regioselectively, via [2,3]sigmatropic rearrangement of phenoxysulfonium ylides. The ortho-alkylated phenols thus obtained were cyclized with concentrate HCl in MeOCH2CH2OH to 1-benzofuran II (R, R1 = as above). 2-Methyl- and 2-phenyl-1-benzofuran were prepared similarly.

Journal of the Chemical Society, Perkin Transactions 3: Organic and Bio-Organic Chemistry published new progress about Alkylation. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Product Details of C10H10O2.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Tabanca, Nurhayat published the artcileEssential Oil Composition of Pimpinella cypria and its Insecticidal, Cytotoxic, and Antimicrobial Activity, Name: 5-Methoxy-2-methylbenzofuran, the main research area is Pimpinella essential oil insecticidal antimicrobial.

A water-distilled essential oil (EO) from the aerial parts of Pimpinella cypria Boiss. (Apiaceae), an endemic species in northern Cyprus, was analyzed by GC-FID and GC-MS. Forty-five compounds were identified in the oil, which comprised 81.7% of the total composition The compound classes in the oil were oxygenated sesquiterpenes (33.9%), sesquiterpenes (22.0%), monoterpenes (11.4%), oxygenated monoterpenes (2.6%), and phenylpropanoids (7.5%). The main components of the oil were (Z)-β-farnesene (6.0%), spathulenol (5.9%), ar-curcumene (4.3%), and 1,5-epoxy-salvial(4)14-ene (3.8%). The P. cypria EO deterred yellow fever mosquitoes (Aedes aegypti) from biting at a concentration of 10 μg/cm2 in in vitro bioassays. The oil was tested for repellency in assays using human volunteers. The oil had a min. effective dosage (MED) for repellency of 47 ± 41 μg/cm2 against Ae. aegypti, which was less efficacious than the pos. control N,N-diethyl-3-methylbenzamide (DEET). In larval bioassays, P. cypria EO showed an LC50 value of 28.3 ppm against 1st instar Ae. aegypti larvae. P. cypria EO demonstrated dose dependent repellency against nymphs of the lone star tick, Amblyomma americanum. Between 45.0% and 85.0% repellency was observed at concentrations ranging from 26 to 208 μg/cm2. However, P. cypria EO was less effective compared with DEET in the tick bioassays. Cytotoxicity assays showed that the P. cypria EO did not exhibit significant effects up to the maximum treatment concentration of 50 μg/mL on HEK293, PC3, U87MG, and MCF cells. P. cypria EO also demonstrated moderate antimicrobial activity against Gram-neg. and -pos. bacteria with MICs ranging from 15.6 to 62.5 μg/mL, except for Candida albicans, which showed the same MIC value of 7.8 μg/mL as the pos. control, flucytosine. This is the first report on the chem. composition of P. cypria EO and its insecticidal, toxicant, cytotoxic, and antimicrobial activity.

Natural Product Communications published new progress about Aedes aegypti. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Name: 5-Methoxy-2-methylbenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Okuyama, Tadashi published the artcileSubstituent effects in the benzofuran system. III. Cationic polymerization, Recommanded Product: 6-Methoxybenzofuran, the main research area is benzofuran polymerization substituent effect.

Cationic copolymerization of pairs of benzofuran derivatives have been carried out in CH2Cl2 using SnCl4-CCl3CO2H (2:1) as catalyst at 0°. Effects of 2- and 3-Me substitutions on the monomer reactivity ratio suggested that the polymeric cation added at the 2-C of benzofuran. Anal. of the effects of 5- and 6-substituents on the reactivity revealed that the transmission efficiency of electronic effects through the two paths, the bonds 8-3 and 9-1-2, was comparable in magnitude. The transition state of the propagation step resembled a bridged carbonium ion intermediate.

Bulletin of the Chemical Society of Japan published new progress about Polymerization. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Recommanded Product: 6-Methoxybenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Song, Shu-Yong published the artcileAn improved and scale-up synthesis of 6-hydroxybenzofuran, Synthetic Route of 50551-63-8, the main research area is hydroxybenzofuran green synthesis scale up.

An optimized process for the preparation of 6-hydroxybenzofuran is described. This process consists of three steps: the reaction of 2-hydroxy-4-methoxybenzaldehyde with chloroacetic acid, the formation of the 6-methoxybenzofuran in acetic anhydride, and the demethylation with sodium 1-dodecanethiolate to afford the desired product. The entire process is safe, cost effective, environmentally benign, and scalable. A production scale of over 2.6 kg product was achieved in good overall yield.

Research on Chemical Intermediates published new progress about Green chemistry. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Synthetic Route of 50551-63-8.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Martin-Santamaria, Sonsoles published the artcileNew scaffolds for the design of selective estrogen receptor modulators, Recommanded Product: 6-Methoxybenzofuran, the main research area is estrogen receptor modulator antitumor pancreatic cancer.

In the present work we report the synthesis of four new ER ligands which can be used as scaffolds for the introduction of the basic side chains necessary for antiestrogenic activity. Affinities and agonist/antagonist characterization of the ligands for both ERα and ERβ have been determined in a competitive radioligand assay, and in an in vitro coactivator recruitment functional assay, resp. Mol. modeling techniques have been used in order to rationalize the exptl. results. Compound 2 is reported as a novel ERβ-agonist/ERα-antagonist. Two compounds show an interesting antitumor profile towards two pancreatic cancer cell lines and have been selected for in vivo assays.

Organic & Biomolecular Chemistry published new progress about Antitumor agents. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Recommanded Product: 6-Methoxybenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Fabian, Walter published the artcileInterpretation of the influence of substituents on the UV spectra of benzofurans, Application In Synthesis of 50551-63-8, the main research area is UV benzofuran derivative substituent effect.

The electronic excitation energies of 12 isometric methoxy- and nitrobenzofuran were calculated by means of PPP and CNDO/S-CI method. Based on the results of a configuration anal., a simple mols.-in-mol.-type model is proposed which in a semiquant. manner completely accounts for the characteristic dependence of the UV spectra of these compounds on the position of the substituent.

Zeitschrift fuer Naturforschung, Teil A: Physik, Physikalische Chemie, Kosmophysik published new progress about Quantum chemistry. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Application In Synthesis of 50551-63-8.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Clough, John M. published the artcileTransition metal-mediated organic synthesis: synthesis of moracin M, Category: benzofurans, the main research area is halobenzofuran metalloresorcinol chromium carbonyl coupling; metallobenzofuran haloresorcinol chromium carbonyl coupling; coupling benzofuran resorcinol palladium catalyst; moracin M.

The Pd-catalyzed cross-coupling of 2-halo- or 2-metallobenzofurans with both 5-metallo- or 5-haloresorcinol tricarbonyl chromium(0) complexes or with the uncomplexed resorcinols, has been evaluated and in consequence, moracin M (I) has been synthesized in good yield by the cross-coupling of 6-(tert-butyldiphenylsiloxy)-2-trimethylstannylbenzofuran with 5-iodoresorcinol bis(triisopropylsilyl) ether and fluoride ion deprotection of the product.

Tetrahedron Letters published new progress about Coupling reaction. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Category: benzofurans.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem