1006-33-3

Usage

Uses

Used in Chemical Synthesis:
2'-BROMO-5'-FLUOROACETOPHENONE is used as a synthetic intermediate for the production of oxabicyclic compounds. Its unique structure allows for the formation of these complex molecules, which have potential applications in various fields, including pharmaceuticals and materials science.
Additionally, 2'-BROMO-5'-FLUOROACETOPHENONE is used as a key component in the enantioselective synthesis of chiral 3-aryl-1-indanone molecules. These chiral molecules are important in the development of enantiomerically pure compounds, which are crucial for various applications, such as pharmaceuticals, agrochemicals, and fragrances. The enantioselective synthesis of these molecules using 2'-BROMO-5'-FLUOROACETOPHENONE allows for the creation of optically active compounds with specific biological activities and properties.

Upstream product

• 676-58-4 methylmagnesium chloride 
• 57381-39-2 2-bromo-5-fluorobenzonitrile 
• 394-28-5 2-Bromo-5-fluorobenzoic acid 
• 94569-84-3 2-bromo-5-fluorobenzaldehyde 
• 906673-56-1 1-(2′-bromo-5′-fluorophenyl)ethan-1-ol 
• 1246078-73-8 methyl 3-(2-bromo-5-fluorophenyl)-3-oxopropionate 
• 75-16-1 methylmagnesium bromide 
• 313547-14-7 2-bromo-5-fluoro-N-methoxy-N-methylbenzamide 

Downstream Products

• 1246078-71-6 1-(2-bromo-5-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one 
• 1427446-94-3 2-bromo-1-(2-bromo-5-fluorophenyl)ethan-1-one 
• 1422961-02-1 (E)-3-(4-chlorophenyl)-1-(5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)prop-2-en-1-one 
• 1422961-15-6 (3S)-3-(4-chlorophenyl)-6-fluoroindan-1-one 
• 1379534-72-1 C₁₆H₂₅FOSi₂ 
• 1374227-76-5 5-fluoro-3-methyl-1-phenyl-1H-indazole 
• 1380424-26-9 6-fluoro-1,2-diphenylquinolin-4(1H)-one 
• 1350844-26-6 1-(5-fluoro-2-(pent-1-ynyl)phenyl)ethanone 
• 1232403-39-2 (R)-1-(2-bromo-5-fluorophenyl)ethan-1-ol 

Relevant academic research and scientific papers

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis

A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.

Intramolecular One-Carbon Homologation of Unstrained Ketones via C-C Activation-Enabled 1,1-Insertion of Alkenes

Here, we describe the development of a Rh-catalyzed intramolecular one-carbon homologation of unstrained aryl ketones through a formal 1,1-insertion process of olefins, enabled by temporary directing group (TDG)-aided C-C activation. The reaction provides a distinct approach to access various substituted 1-indanones. Computational mechanistic studies reveal that the formal 1,1-insertion is realized by a selective C(sp2)-C(sp3) activation and turnover limiting 2,1-insertion into the alkene, followed by a facile β-H elimination and reinsertion process.

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations

A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).

NOVEL INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)

The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.

Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization

We describe a copper-catalyzed intramolecular reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst undergo isomerization and selective intramolecular allylation of the (E)-allylcopper form of the major product through a six-membered boatlike transition state. The resulting products were further transformed to fully saturated naphthalene-1-ols by reactions of the olefin moiety.

6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)

The present invention relates generally to antiviral agents. Specifically, the present invention relates to compounds of formula I which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.

NOVEL 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)

The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for mating the compounds.

NOVEL OXALYL PIPERAZINES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)

The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.