55038-01-2

Usage

InChI:InChI=1/C9H8O2/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-5,10H,6H2

Upstream product

• 62452-62-4 benzofuran-2-ylmethyl acetate 
• 4265-16-1 2-formylbenzo[b]furan 
• 533-58-4 2-Iodophenol 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 3199-61-9 ethyl coumarilate 
• 271-89-6 1-benzofurane 
• 32865-61-5 2-iodophenyl acetate 
• 680220-89-7 2-(1-methoxycarbonyloxy-2-propynyl)phenol 
• 184368-89-6 1-iodo-2-(tert-butyldimethylsilyloxy)benzene 
• 853296-76-1 3-(2-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-yn-1-ol 
• 90-02-8 salicylaldehyde 
• 107-19-7 propargyl alcohol 
• 680221-20-9 2-benzofuranylmethyl methyl malonate 
• 1646-27-1 methyl benzofuran-2-carboxylate 

Downstream Products

• 116004-82-1 <(1-Benzofuran-2-yl)methyl>triphenylphosphoniumbromid 
• 4265-16-1 2-formylbenzo[b]furan 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 1454785-18-2 1-((benzofuran-2-yl)methyl)-3-(2-(4-bromophenyl)-2-oxoethyl)-1H-imidazol-3-ium bromide 
• 1454785-20-6 1-((benzofuran-2-yl)methyl)-3-(2-(2-bromobenzyl))-1H-imidazol-3-ium bromide 
• 1454785-23-9 1-((benzofuran-2-yl)methyl)-3-(2-oxo-2-phenylethyl)-1H-benzo[d]imidazol-3-ium bromide 
• 1454785-24-0 C₂₅H₂₁N₂O₃⁽¹⁺⁾*Br^(1-) 
• 1454785-25-1 1-((benzofuran-2-yl)methyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-1H-benzo[d]imidazol-3-ium bromide 
• 1454785-26-2 1-((benzofuran-2-yl)methyl)-3-(2-(4-bromophenyl)-2-oxoethyl)-1H-benzo[d]imidazol-3-ium bromide 
• 1454785-28-4 1-((benzofuran-2-yl)methyl)-3-(2-oxo-1,2-diphenylethyl)-1H-benzo[d]imidazol-3-ium bromide 
• 1454785-29-5 1-((benzofuran-2-yl)methyl)-3-(2-(2-bromobenzyl))-1H-benzo[d]imidazol-3-ium bromide 
• 1454785-31-9 1-((benzofuran-2-yl)methyl)-3-(2-oxo-2-phenylethyl)-2-methyl-1H-imidazol-3-ium bromide 
• 1454785-32-0 1-((benzofuran-2-yl)methyl)-3-(2-(4-methoxyphenyl)-2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide 
• 1454785-33-1 1-((benzofuran-2-yl)methyl)-3-(2-(4-hydroxyphenyl)-2-oxoethyl)-2-methyl-1H-imidazol-3-ium bromide 

Relevant academic research and scientific papers

COMPOUND FOR INHIBITING PGE2/EP4 SIGNALING TRANSDUCTION INHIBITING, PREPARATION METHOD THEREFOR, AND MEDICAL USES THEREOF

A compound of formula (I), a preparation method therefor, a pharmaceutical composition containing a derivative thereof, and the therapeutic uses thereof, especially inhibiting PGE2/EP4 signalling transduction and the uses thereof for treating cancer, acute or chronic pain, migraine, osteoarthritis, rheumatoid arthritis, gout, bursitis, ankylosing spondylitis, primary dysmenorrhea, tumour or arteriosclerosis.

Immunomodulator

The invention discloses an immunomodulator, and particularly relates to compounds for inhibiting IL-17A and application of the compounds serving as the immunomodulator in preparation of drugs. The invention discloses an application of a compound shown as a formula I or a stereoisomer thereof in preparing medicines for inhibiting IL-17A, and provides a new choice for clinically screening and/or preparing medicines for treating diseases related to IL-17A activity.

Immunomodulator

The invention discloses an immunomodulator, and particularly relates to a compound shown as a formula I, or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. Experiments prove that the compound has good IL-17A inhibitory activity, can be used for preparing an IL-17A inhibitor and drugs for preventing and/or treating IL-17A mediated diseases (such as inflammation, autoimmune diseases, infectious diseases, cancers and precancerous syndromes), and provides a new medical possibility for clinical treatment of diseases related to abnormal IL-17A activity.

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions

Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Nickel-Catalyzed Amination of α-Aryl Methyl Ethers

α-Aryl amines are prevalent in pharmaceutically active compounds and natural products. Herein, we describe a Ni-catalyzed protocol for their synthesis from readily available α-aryl ethers. While α-aryl ethers have been used as electrophiles in Ni-catalyzed C-C bond formations, their use in C-heteroatom bond formation is much less prevalent. Preliminary mechanistic insight suggests that oxidative addition is facilitated by an anionic ligand and that reductive elimination is a reversible process.

Palladium-catalyzed Tsuji-Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles

The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the η3-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans. This journal is

Bulky N-Heterocyclic-Carbene-Coordinated Palladium Catalysts for 1,2-Addition of Arylboron Compounds to Carbonyl Compounds

The synthesis of primary, secondary, and tertiary alcohols by the 1,2-addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N-heterocyclic carbene (NHC)-coordinated 2,6-di(pentan-3-yl)aniline (IPent)-based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS-IPent-CYP-catalyzed reactions are efficient at low catalyst loadings (0.02–0.3 mol% Pd), and the exceptional catalytic activity for 1,2-addition is attributed to the steric bulk of the NHC ligand. These reactions can yield a wide range of functionalized benzylic alcohols that are difficult to synthesize by classical protocols using highly active organomagnesium or lithium reagents.

Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine

Facile reduction of aryl halides with a combination of 5% Pd/C, B2(OH)4, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B2(OD)4 was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed and increased in slower reactions. 4-Methylmorpholine was identified as a possible source of H atoms in this, but a combination of only 4-methylmorpholine and Pd/C did not result in reduction. Hydrogen gas has been observed to form with this reagent combination. Experiments aimed at understanding the chemistry led to the proposal of a plausible mechanism and to the identification of N,N-bis(methyl-d3)pyridin-4-amine (DMAP-d6) and B2(OD)4 as an effective combination for full aromatic deuteriation. (Figure presented.).