Category: 19301-35-0

The important role of C8H6OS

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Addition Reactions of Benzothiophen. Part 4. Reactions of Some Acetoxy- and Hydroxy-benzothiophens with Benzene or Toluene

Heating acetoxybenzothiophens with AlCl3-benzene can give the normal Fries-rearranged products (for the 4-OAc and 7-OAc isomers); these sometimes react further to give their 2,3-dihydro- (for 4-OAc and 7-OAc) or 2-phenyl derivatives (for 6-OAc).Alternatively, benzene can add across the 2,3-double bond of the acetoxy-compound, to give the 2- (for 6-OAc) or 3-phenyl-2,3-dihydrobenzothiophens (for 7-Oac).With AlCl3 in dichloromethane, 6-acetoxybenzothiophen undergoes intermolecular transfer of an acetyl group to give a mixture of 6-acetoxy-2- and 3-acetylbenzothiophens and 6-hydroxybenzothiophen.With AlCl3 in benzene at room temperature, 4-acetoxybenzothiophen gives a rearranged product, 4,5-dihydro-2,4-diphenylbenzothiophen-7(6H)-one (3a) (17percent).In the presence of AlCl3 for 0.5 h, 4-, 5-, 6-, and 7-hydroxybenzothiophens undergo addition of benzene or toluene, to give the appropriate 2-aryl-2,3-dihydrohydroxybenzothiophens (1).Yields are high for the 4- and 6-hydroxy-isomers (80-85percent), but lower for the 5- (55percent) and 7-isomers (10percent).In each of these reactions the starting hydroxybenzothiophen is partly converted into its 2,3-dihydro-derivative. 5- and 7-Hydroxybenzothiophen also each give the same 4,5-dihydro-2,4-diarylbenzothiophen-7(6H)-one (3) (25percent) in this reaction.When the reaction period with benzene or toluene is extended to 5 days, the amount of solvent addition product (1) decreases, but all four hydroxy-isomers now give the same rearranged product (3).The mechanism of this unusual rearrangement is discussed in terms of a spiro-intermediate.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Extracurricular laboratory:new discovery of Benzo[b]thiophen-5-ol

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Chemistry is traditionally divided into organic and inorganic chemistry. Computed Properties of C8H6OS, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent，Which mentioned a new discovery about 19301-35-0

Synthesis and biological evaluation of 3-heteroaryloxy-4-phenyl-2(5H)-furanones as selective COX-2 inhibitors

A series of 3-heteroaryloxy-4-phenyl-2-(5H)-furanones were prepared and evaluated for their potency and selectivity as COX-2 inhibitors. This led to the identification of L-778,736 as a potent, orally active and selective inhibitor of the COX-2 enzyme.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Simple exploration of C8H6OS

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Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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GPR119 AGONIST

A compound represented by the formula (II) is a GPR119 agonist, and is used as an agent for treating diabetes: wherein each of R23, R24, and R25 is hydrogen, halogen, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylsulfonyl, or the like; each of Q0 and T0 is CH2 or the like, or Q0 and T0 are combined to form CH=CH or the like; A0 is (CH2)p, C(O), or a bond; B0 is a bond or the like; one of U0 and V0 is N, and the other is CR31 or the like; each of X0 and Y0 is CH2CH2 or the like; Z0 is C(O)OR32 or the like; and each of R21 and R22 is hydrogen, a halogen atom, hydroxyl, C1-8 alkyl, or the like.

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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

The important role of 19301-35-0

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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. The reactant in an enzyme-catalyzed reaction is called a substrate. category: benzothiophene, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 19301-35-0, Name is Benzo[b]thiophen-5-ol, molecular formula is C8H6OS

4-Benzofuranyloxynicotinamide derivatives are novel potent and orally available TGR5 agonists

A series of 4-benzofuranyloxynicotinamide derivatives were identified to be novel, potent, and orally available TGR5 agonists. Among them, compound 9r had the highest potency in vitro (hTGR5 EC50 = 0.28 nM, mTGR5 EC 50 = 0.92 nM). Further in vivo studies disclosed that 9r could effectively lower the blood glucose, but meantime caused an increase in the gallbladder volume of mice. Subsequent research toward eliminating the gallbladder toxicity resulted in compound 19 with low permeability. Although the EC50 of mTGR5 of 19 was larger one order than that of 9r, it still had good glucose-lowing activity. Nevertheless, 19 also caused the adverse effects to the gallbladder. The drug levels detection disclosed that the concentration of 19 was only lower than that of 9r in plasma but was higher in bile and gallbladder tissue. This result indicated that low exposure in plasma could not guarantee low exposure in bile and gallbladder tissue, and thus resulting in the gallbladder toxicity of 19.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

The Absolute Best Science Experiment for Benzo[b]thiophen-5-ol

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Bismuth(III)-catalyzed dehydrative etherification and thioetherification of phenolic hydroxy groups

Use of a bismuth catalyst allowed efficient dehydrative substitution of phenolic hydroxy groups with alcohols and thiols to form C-O and C-S bonds. The reaction required equimolar amounts of two readily available substrates that generated H2O as the only byproduct. The relatively mild reaction conditions were compatible with the functional groups selected, and provided excellent chemoselectivity.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Final Thoughts on Chemistry for 19301-35-0

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Studies in Sulphur Heterocycles: Part III – Syntheses of Tricyclic Compounds with Condensed Thiophene Rings

Some members of the thieno<3,2-e><1>benzothiophene, <1>benzothieno<3,2-b>pyrrole, thieno<2,3-g>-1,2-benzisoxazole and thieno<2,3-g>indazole ring systems have been synthesized from 6,7-dihydrobenzothiophen-4(5H)-one derivatives.The unsaturated ethers of 4- and 5-hydroxybenzothiophenes undergo Claisen rearrangement followed by ring closure to give thieno<2,3-h><1>benzopyran and thieno<3,2-e><1>benzopyran ring systems.Syntheses of new thienobenzofurans from 4-hydroxybenzothiophene-5-carbaldehyde, its 2-methyl derivative and 5-hydroxybenzothiophene-4-carbaldehyde are also described.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Extracurricular laboratory:new discovery of Benzo[b]thiophen-5-ol

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Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst

A method for the hydroxylation of aryl and heteroaryl halides, promoted by a catalyst based on a biarylphosphine ligand tBuBrettPhos (L5) and its corresponding palladium precatalyst (1), is described. The reactions allow the cross-coupling of both potassium and cesium hydroxides with (hetero)aryl halides to afford a variety of phenols and hydroxylated heteroarenes in high to excellent yield.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

More research is needed about C8H6OS

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19301-35-0, Name is Benzo[b]thiophen-5-ol, belongs to benzothiophene compound, is a common compound. HPLC of Formula: C8H6OSIn an article, once mentioned the new application about 19301-35-0.

Synthesis and studies on spectroscopic as well as electron donating properties of the two alkoxy benzo[b]thiophenes

Synthesis, characterization, steady state and time resolved, using time correlated single photon counting as well as laser flash photolysis techniques, spectroscopic investigations were made for two alkoxy benzo[b]thiophene molecules: 5-methoxy benzo[b]thiophene (5MBT) and 5-methoxymethyl benzo[b]thiophene (5MMBT). In both non-polar n-heptane (NH) and polar acetonitrile (ACN) solvents and at ambient temperature the electronic absorption spectra of these thiophenes exhibit different band systems whose assignments were made from the measurements of the steady state excitation polarization spectra. Steady state fluorescence spectra of these molecules in the different polarity solvents show the presence of non-specific interactions. From the redox properties of the benzothiophenes, measured by cyclic voltammetry, their electron donating properties were observed in the presence of the well-known electron acceptor 9cyanoanthracene (9CNA). Further, detailed studies by laser flash photolysis techniques show that ion-recombination mechanism predominates after the initial excitation of the acceptor moiety using the third harmonic of Nd:YAG laser. This recombination together with the external heavy atom effect (the donor containing ‘sulphur’ atom) appears to be responsible for the formation of the triplet of the monomeric acceptor 9CNA. From the steady state experiments it is shown that both in non-polar NH and highly polar ACN the quenching in the fluorescence emission of 9CNA in the presence of the benzothiophene donors is brought about primarily by the external heavy atom effect and in ACN, although the presence of the photoinduced ET reaction is confirmed, this process seems, from the observed bimolecular dynamic quenching rate, kq, to be significantly masked by the external heavy atom effect.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Some scientific research about 19301-35-0

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New heteroaryl carbamates: Synthesis and biological screening in vitro and in mammalian cells of wild-type and mutant HIV-protease inhibitors

New heteroaryl HIV-protease inhibitors bearing a carbamoyl spacer were synthesized in few steps and high yield, from commercially available homochiral epoxides. Different substitution patterns were introduced onto a given isopropanoyl-sulfonamide core that can have either H or benzyl group. The in vitro inhibition activity against recombinant protease showed a general beneficial effect of both carbamoyl moiety and the benzyl group, ranging the IC50 values between 11 and 0.6 nM. In particular, benzofuryl and indolyl derivatives showed IC50 values among the best for such structurally simple inhibitors. Docking analysis allowed to identify the favorable situation of such derivatives in terms of number of interactions in the active site, supporting the experimental results. The inhibition activity was also confirmed in HEK293 mammalian cells and was maintained against protease mutants. Furthermore, the metabolic stability was comparable with that of the commercially available inhibitors.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem