38871-41-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-Dihydro-1,4-benzodioxine-5-carbonyl chloride is used as a reagent for the synthesis of pharmaceutical compounds and other biologically active molecules. Its ability to form carbon-carbon and carbon-heteroatom bonds makes it a key component in the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3-Dihydro-1,4-benzodioxine-5-carbonyl chloride is used as a versatile reagent for the formation of various chemical bonds. Its mild reaction conditions and compatibility with a wide range of substrates contribute to its popularity in the synthesis of complex organic molecules.
Used in Drug Discovery and Development:
2,3-Dihydro-1,4-benzodioxine-5-carbonyl chloride is employed as a reagent in drug discovery and development processes. Its potential applications in the synthesis of novel compounds with therapeutic properties make it a valuable asset in the search for new treatments and medications.
Used in Chemical Research:
In chemical research, 2,3-Dihydro-1,4-benzodioxine-5-carbonyl chloride is utilized for studying the properties and reactions of chlorinated carbonyl compounds. Its unique structure and reactivity provide insights into the development of new synthetic methods and strategies in organic chemistry.

InChI:InChI=1/C9H7ClO3/c10-9(11)6-2-1-3-7-8(6)13-5-4-12-7/h1-3H,4-5H2

Upstream product

• 4442-53-9 2,3-dihydro-1,4-benzodioxine-5-carboxylic acid 
• 214894-91-4 2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid methyl ester 
• 2411-83-8 methyl-2,3-dihydroxybenzoate 
• 303-38-8 2,3-Dihydroxybenzoic acid 

Downstream Products

• 349550-81-8 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide 
• 148703-14-4 2,3-dihydro-benzo[1,4]dioxin-5-carbonitrile 
• 66411-50-5 N-(1-ethyl-2-pyrrolidylmethyl)-1,4-benzodioxane-5-carboxamide hydrochloride 
• 66411-12-9 N-(1-benzyl-4-piperidyl)-1,4-benzodioxane-5-carboxamide hydrochloride 
• 532391-79-0 C₂₂H₂₆N₂O₄ 
• 1400250-82-9 C₂₃H₁₇BrN₄O₃ 
• 1400250-84-1 C₂₃H₁₇ClN₄O₃ 
• 274910-20-2 2-(2,3-dihydro-1,4-benzodioxin-5-yl)acetic acid 
• 1092477-62-7 (+/-)-N'-[3,5-bis(trifluoromethyl)phenyl]-2-(2,3-dihydro-1,4-benzodioxin-5-yl)-2-(4-methyl-1-piperazinyl)acetohydrazide 
• 1092476-37-3 (R)-N'-[3,5-bis(trifluoromethyl)phenyl]-2-(2,3-dihydro-1,4-benzodioxin-5-yl)-2-(4-methyl-1-piperazinyl)acetohydrazide 
• 1092476-36-2 (S)-N'-[3,5-bis(trifluoromethyl)phenyl]-2-(2,3-dihydro-1,4-benzodioxin-5-yl)-2-(4-methyl-1-piperazinyl)acetohydrazide 
• 1609584-26-0 2-((Z)-2-styryl-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydro-1,4-benzodioxine-5-carboxylate 
• 1609584-24-8 2-((Z)-2-(2-fluoro-6-chlorostyryl)-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydro-1,4-benzodioxine-5-carboxylate 
• 1609584-23-7 2-((Z)-2-(4-methoxystyryl)-5-nitro-1H-imidazol-1-yl)ethyl 2,3-dihydro-1,4-benzodioxine-5-carboxylate 

Relevant academic research and scientific papers

Heterocyclic compound and preparation and application thereof

The invention relates to bromodomain inhibitors, and provides a compound represented by a general formula I, a pharmaceutically acceptable salt, an enantiomer, a diastereoisomer, an atropisomer, a racemate, a polymorph, a solvate or an isotope-labeled compound (including deuterium substitution) thereof, a preparation method thereof, a pharmaceutical composition containing the same, and applicationthereof in pharmacy.

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.

Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent

The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.

Demonstrating In-Cell Target Engagement Using a Pirin Protein Degradation Probe (CCT367766)

Demonstrating intracellular protein target engagement is an essential step in the development and progression of new chemical probes and potential small molecule therapeutics. However, this can be particularly challenging for poorly studied and noncatalyt

Discovery of a Chemical Probe Bisamide (CCT251236): An Orally Bioavailable Efficacious Pirin Ligand from a Heat Shock Transcription Factor 1 (HSF1) Phenotypic Screen

Phenotypic screens, which focus on measuring and quantifying discrete cellular changes rather than affinity for individual recombinant proteins, have recently attracted renewed interest as an efficient strategy for drug discovery. In this article, we describe the discovery of a new chemical probe, bisamide (CCT251236), identified using an unbiased phenotypic screen to detect inhibitors of the HSF1 stress pathway. The chemical probe is orally bioavailable and displays efficacy in a human ovarian carcinoma xenograft model. By developing cell-based SAR and using chemical proteomics, we identified pirin as a high affinity molecular target, which was confirmed by SPR and crystallography.

Cobalt-Catalyzed C(sp2)?H Methylation by using Dicumyl Peroxide as both the Methylating Reagent and Hydrogen Acceptor

The first cobalt-catalyzed direct methylation of a C(sp2)?H bond using dicumyl peroxide (DCP) as both the methylating reagent and hydrogen acceptor has been established. The reaction proceeded without the use of any additives, and was proven to be applicable to various amides bearing a 2-pyridinylisopropyl (PIP) directing group, providing an efficient access to o-methyl aryl amides with high functional-group tolerance. Preliminary mechanistic studies suggest a radical process would be involved in the catalytic process.

Synthesis, biological evaluation, and molecular docking studies of novel 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxan moiety as FAK inhibitors with anticancer activity

A series of 2-styryl-5-nitroimidazole derivatives containing 1,4-benzodioxan moiety (3a-3r) has been designed, synthesized and their biological activities were also evaluated as potential antiproliferation and focal adhesion kinase (FAK) inhibitors. Among all the compounds, 3p showed the most potent activity in vitro which inhibited the growth of A549 with IC 50 value of 3.11 μM and Hela with IC50 value of 2.54 μM respectively. Compound 3p also exhibited significant FAK inhibitory activity (IC50 = 0.45 μM). Docking simulation was performed for compound 3p into the FAK structure active site to determine the probable binding model.

Discovery of agonists of cannabinoid receptor 1 with restricted central nervous system penetration aimed for treatment of gastroesophageal reflux disease

Agonists of the cannabinoid receptor 1 (CB1) have been suggested as possible treatments for a range of medical disorders including gastroesophageal reflux disease (GERD). While centrally acting cannabinoid agonists are known to produce psychotropic effects, it has been suggested that the CB1 receptors in the periphery could play a significant role in reducing reflux. A moderately potent and highly lipophilic series of 2-aminobenzamides was identified through focused screening of GPCR libraries. Development of this series focused on improving potency and efficacy at the CB1 receptor, reducing lipophilicity and limiting the central nervous system (CNS) exposure while maintaining good oral absorption. Improvement of the series led to compounds having excellent potency at the CB1 receptor and high levels of agonism, good physical and pharmacokinetic properties, and low penetration into the CNS. A range of compounds demonstrated a dose-dependent inhibition of transient lower esophageal sphincter relaxations in a dog model.

Discovery of 6-substituted 4-anilinoquinazolines with dioxygenated rings as novel EGFR tyrosine kinase inhibitors

It had been reported that some dioxygenated rings fusing with the quinazoline scaffold could lead to new EGFR inhibitors. Based on this, several kinds of oxygenated alkane quinazoline derivatives were synthetized and evaluated as EGFR inhibitors. Their antiproliferative activities were tested against four cancer cell lines: A431, MCF-7, A549, and B16-F10. Most derivatives could counteract EGF-induced EGFR phosphorylation, and their potency was comparable to the reference compound Erlotinib. The size of the fused dioxygenated ring was crucial for the biological activity and the heptatomic ring derivative 19 showed potent in vitro inhibitory activity in the enzymatic assay as well as in the cellular assay.

Synthesis, crystal structures, insecticidal activities, and structure-activity relationships of novel N ′- Tert -Butyl- N ′-substituted-benzoyl- N -[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1, 3]([1,4])dioxine}carbohydrazide derivatives

Several series of novel N′-tert-butyl-N′-substituted-benzoyl-N- [di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by 1H NMR spectra, HRMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N-tert-butyl-N,N′- diacylhydrazines show significant selectivities to different lepidopterous pests.