227752-25-2

Usage

Chemical Class

Benzofuran

Explanation

1-Benzofuran-6-yl trifluoromethanesulfonate belongs to the class of organic compounds known as benzofurans, which are compounds containing a benzene ring fused to a furan ring.

Explanation

The molecular formula represents the number of atoms of each element present in a molecule of the compound.

Explanation

The compound contains the trifluoromethanesulfonyl (CF3SO2-) functional group, which is a type of ester.

Explanation

1-Benzofuran-6-yl trifluoromethanesulfonate is commonly used as a reagent in organic synthesis, which involves the formation of new chemical compounds from simpler substances.

Explanation

Trifluoromethanesulfonate esters are often used as protecting groups for alcohols, which means they can be added to an alcohol molecule to prevent it from reacting in certain situations.

Explanation

In nucleophilic substitution reactions, the trifluoromethanesulfonate group can act as a leaving group, meaning it can be replaced by a nucleophile to form a new compound.

Explanation

1-Benzofuran-6-yl trifluoromethanesulfonate is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, which are chemicals used in the medical and agricultural industries, respectively.

Explanation

The compound has various other applications in the field of chemistry, including research and development, material science, and chemical engineering.

Functional Group

Trifluoromethanesulfonate ester

Use as a Reagent

Organic synthesis

Protecting Groups

Alcohols

Leaving Groups

Nucleophilic substitution reactions

Applications

Pharmaceutical and agrochemical synthesis

Other Applications

Various fields in chemistry

Upstream product

• 13196-11-7 6-hydroxybenzofuran 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 299912-77-9 6-(tert-butyl-dimethylsilanyloxy)-[2H]-benzofuran-3-one 
• 1056942-29-0 3-hydroxy-6-silyloxy-[2,3]dihydrobenzofuran 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1020947-92-5 6-hydroxy-2,3-dihydrobenzofuran-3-ol 

Downstream Products

• 123297-88-1 benzofuran-6-carboxaldehyde 
• 527679-33-0 2-benzofuran-6-yl-3-benzyloxyamino-propionic acid ethyl ester 
• 204452-96-0 (S)-3-Benzofuran-6-yl-3-[benzyl-((R)-1-phenyl-ethyl)-amino]-propionic acid ethyl ester 
• 588703-29-1 methyl benzofuran-6-carboxylate 
• 77095-51-3 benzofuran-6-carboxylic acid 
• 1332331-21-1 4-[4-(1-benzofuran-6-yl)phenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1194550-67-8 ((S)-benzyl 2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-methylsulfonyl)phenyl)propanoate 
• 1025967-78-5 (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid 
• 17450-68-9 benzo[b]furan-6-carbonitrile 
• 1083168-69-7 (2,3-dihydrobenzofuran-6-yl)methanol 

Relevant academic research and scientific papers

Concise synthesis of 6-cyanobenzo[ b ]furan, a useful building block

A new three-step synthesis of 6-cyanobenzo[b]furan (6) was developed, starting from commercially available 6-hydroxybenzo[b]furan-3-one (18). Key steps in this process were the first step, which was the reductive dehydration of 18 to produce 6-hydroxybenzo[b]furan (19), and the last step, which converted the aryl triflate 20 to the aryl cyanide 6 in a palladium-catalyzed cross-coupling protocol. Overall yield for this new synthesis was 49%.

LFA-1 INHIBITOR AND POLYMORPH THEREOF

Methods of preparation and purification of a compound, intermediates thereof, a polymorph thereof, and related compounds are disclosed. Formulations and uses thereof in the treatment of LFA -1 mediated diseases are also disclosed.

Discovery and development of potent LFA-1/ICAM-1 antagonist SAR 1118 as an ophthalmic solution for treating dry eye

LFA-1/ICAM-1 interaction is essential in support of inflammatory and specific T-cell regulated immune responses by mediating cell adhesion, leukocyte extravasation, migration, antigen presentation, formation of immunological synapse, and augmentation of T-cell receptor signaling. The increase of ICAM-1 expression levels in conjunctival epithelial cells and acinar cells was observed in animal models and patients diagnosed with dry eye. Therefore, it has been hypothesized that small molecule LFA-1/ICAM-1 antagonists could be an effective topical treatment for dry eye. In this letter, we describe the discovery of a potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonist (SAR 1118) and its development as an ophthalmic solution for treating dry eye.

MODULATORS OF CFTR

Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette ("ABC") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator ("CFTR"). The present invention also relates to methods of treating CFTR mediated diseases using compounds of the present invention.

MODULATORS OF CELLULAR ADHESION

The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

Nonpeptide alphavbeta3 antagonists. Part 11: discovery and preclinical evaluation of potent alphavbeta3 antagonists for the prevention and treatment of osteoporosis.

3-(S)-Pyrimidin-5-yl-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid (5e) and 3-(S)-(methylpyrimidin-5-yl)-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid (5f) were identified as potent and selective antagonists of the alpha(v)beta(3) receptor. These compounds have excellent in vitro profiles (IC(50) = 0.07 and 0.08 nM, respectively), significant unbound fractions in human plasma (6 and 4%), and good pharmacokinetics in rat, dog, and rhesus monkey. On the basis of the efficacy shown in an in vivo model of bone turnover following once-daily oral administration, these two compounds were selected for clinical development for the treatment of osteoporosis.

Syntheses of 5- and 6-[2,3]-dihydrobenzofuran β-amino acids

Efficient stereoselective syntheses of 5- and 6-[2,3]-dihydrobenzofuran β-amino acids are described. These 3-aryl β-amino acids are aspartic acid mimetics that are structurally related to known benzodioxole systems. In many cases, the benzodioxole can inhibit and induce cytochrome P-450; neither of these dihydrobenzofuran β-amino esters is a potent inhibitor of several human P-450 enzymes. (C) 2000 Elsevier Science Ltd.