Tag: M.W=150-200

Houbion, J. A. published the artcileThe synthesis of unambiguously substituted 3-hydroxyphthalides, Quality Control of 52010-22-7, the main research area is phthalide hydroxy; hydroxyphthalide; toluate bromination cyclization; formylphenyloxazoline hydrolysis cyclization; oxazolinylbenzaldehyde hydrolysis cyclization.

Hydroxyphthalides I (R = 4-, 6-, 7-Cl; 4-, 6-MeO) were obtained in 61-98% yield by photochem. bromination of II followed by hydrolysis. II (R = 4-MeO, 6-NO2) were obtained from R-2-MeC6H3CO2H by successive bromination and cyclization. I (R = 5-Cl, 5-MeO) were obtained in 63-71% yield by hydrolysis of III. III were obtained by ortho metalation-formylation of para substituted 2-aryloxazolines.

Organic Preparations and Procedures International published new progress about phthalide hydroxy; hydroxyphthalide; toluate bromination cyclization; formylphenyloxazoline hydrolysis cyclization; oxazolinylbenzaldehyde hydrolysis cyclization. 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

Darling, Stephen D. published the artcileLithium-ammonia reduction of benzofurans, Recommanded Product: 5-Methoxy-2-methylbenzofuran, the main research area is FURAN BENZO REDN; BENZO FURAN REDN; BENZOFURANS LITHIUM AMMONIA REDN.

The reduction of 5-methoxy-2-methylbenzofuran (I), 5-methoxybenzofuran (II), 2,3- dihydro – 5 – methoxy – 2 – methylbenzofuran (III), and 2,3-dihydro-5-methoxybenzofuran (IV) with Li-NH3 systems is described. Furan ring opening was observed in the reduction of I or II when a limited amount of alc. was present in the NH3 solution With excess alc., the corresponding 5-methoxy-2,3,4,7-tetrahydrobenzofuran was formed from each substrate. A side product from the reduction of III was 2,3,4,5,6,7-hexahydro-2-methylbenzofuran (V). 21 references.

Journal of Organic Chemistry published new progress about FURAN BENZO REDN; BENZO FURAN REDN; BENZOFURANS LITHIUM AMMONIA REDN. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Recommanded Product: 5-Methoxy-2-methylbenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ni, Yang published the artcileIron-catalyzed cross-dehydrogenative C-H amidation of benzofurans and benzothiophenes with anilines, Computed Properties of 13391-27-0, the main research area is diarylamine preparation; benzofuran aniline cross dehydrogenative amidation iron catalyst; benzothiophene aniline cross dehydrogenative amidation iron catalyst.

An efficient iron-catalyzed cross-dehydrogenative aromatic C-H amidation using DDQ as an oxidant under mild conditions was reported, providing a straightforward access to structurally diverse diarylamines 4-MeC6H4SO2NRR1 [R = 2-butylbenzofuran-3-yl, benzothiophen-3-yl, 4-MeOC6H4, etc.; R1 = 4-MeOC6H4, 3-F-4-MeOC6H3, 4-MeSC6H4, etc.] incorporating benzofuran/benzothiophene motifs. Mechanistic studies indicated that a nitrogen-centered anilino radical was involved in the C-N bond formation.

Organic Chemistry Frontiers published new progress about Amidation. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Computed Properties of 13391-27-0.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

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

Rehan, Mohammad published the artcileSynthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols, Synthetic Route of 13391-27-0, the main research area is cinnamyl phenol palladium oxidative cyclization catalyst; benzofuran benzyl preparation.

Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans I (R1 = 5-Me, 5-OMe, 5-Ph, 4,6-diMe, etc.; R2 = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4, H, Me, etc.; Ar = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4, 1-naphthyl, etc.) via a regioselective 5-exo-trig intramol. oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcs. catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.

Journal of Organic Chemistry published new progress about Alkenylation, cinnamylation. 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

Anderson, Wayne K. published the artcileUse of 2,3-dichloropropene and 1,3-dichlorobut-2-ene as synthons for heterocyclic compounds. Synthesis of 2-methylbenzo[b]furans, 2-methylbenzo[b]thiophenes, and 4-methyl-2H-chromene, Category: benzofurans, the main research area is phenol condensation chloro alkene; thiophenol condensation chloro alkene; cyclization propene arylthio chloro; Claisen rearrangement aryloxychloropropene; benzofuran methyl; benzothiophene methyl; chromene methyl.

Addnl. data considered in indexing and abstracting are available from a source cited in the original document. The ethers I (X = O, R = H, p-Me, p-OMe, p-Cl, o-Me, o-OMe, o-Cl), prepared by condensation of the appropriate phenol with CH2:CClCH2Cl (II), underwent Claisen rearrangement to give the phenols III, acid-catalyzed cyclization of which gave 28-77% benzofurans IV (X = O). The thio ether I (X = S, R = H, p-Me, p-OMe, p-Cl, o-Me), similarly prepared from the appropriate thiophenol and II, cyclized directly on heating in PhNEt2 to give 54-80% benzothiophenes IV (X = S). Condensation of PhOH with MeCCl:CHCH2Cl gave 78% 3-chloro-1-phenoxybut-2-ene, which thermally cyclized to give 64% 4-methyl-2H-chromene.

Journal of the Chemical Society, Perkin Transactions 2: Organic and Bio-Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Category: benzofurans.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem