766-40-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 1371, 1964 DOI: 10.1021/jo01029a024

InChI:InChI=1/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H

Upstream product

• 88-14-2 2-furanoic acid 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 15341-59-0 3,4-dichlorofuran 
• 7697-37-2 nitric acid 
• 117869-21-3 C₁₀H₅BrCl₂O₂S 
• 2892-56-0 cis-α-H-Tetrachlorcrotonylchlorid 
• 40636-99-5 4-chloro-5-hydroxy-<5H>-furan-2-one 
• 3200-96-2 2,3,4,4-tetrachloro-cyclobut-2-en-1-one 
• 98-01-1 furfural 

Downstream Products

• 933-76-6 4,5-dichloro-2-methyl-3(2H)-pyridazinone 
• 83074-09-3 2,3-Dichlor-4,4-bis(4-isopropylphenyl)-2-butensaeure 
• 17180-94-8 5-chloropyrimidine 
• 137257-36-4 7,8-Dichloro-3-phenyl-1,8a-dihydro-2H-pyrrolo[1,2-b][1,2,4,5]tetrazin-6-one 
• 137257-38-6 7,8-Dichloro-2-methyl-3-phenyl-1,8a-dihydro-2H-pyrrolo[1,2-b][1,2,4,5]tetrazin-6-one 
• 137257-39-7 7,8-Dichloro-3-(4-chloro-phenyl)-2-methyl-1,8a-dihydro-2H-pyrrolo[1,2-b][1,2,4,5]tetrazin-6-one 
• 1698-53-9 4,5-dichloro-1-phenylpyridazin-6-one 
• 29814-12-8 3,4-dichloro-5-isopropyloxy-2(5H)-furanone 
• 72857-85-3 α,β-dichloro-γ-phenyl-Δ^α,β-crotonolactone 
• 66980-34-5 2,3-Dichlor-4,4-diphenyl-2-butensaeure 
• 64-18-6 formic acid 

Relevant academic research and scientific papers

Aquaculture used for preventing fouling organisms are attached to and of the ketone derivative and its preparation method

The invention belongs to the technical field of medicine and provides furanone derivatives as shown in a formula (I) described in the specification or pharmaceutically acceptable salts thereof. The invention further provides a preparation method and application of the furanone derivatives or pharmaceutically acceptable salts thereof which are used as main active ingredients for inhibiting diseases and insect pests of marine products and biofouling.

Sulfides, sulfones, and sulfoxides of the furan-2(5H)-one series. synthesis and structure

A number of 4- and 5-R-sulfanylfuran-2(5H)-one derivatives were synthesized, and their oxidation with various reagents was studied. The corresponding sulfones were obtained using hydrogen peroxide in acetic acid. 4-R-sulfanyl derivatives were selectively oxidized to sulfoxides with m-chloroperoxybenzoic acid. The molecular and crystal structures of some new sulfones and sulfoxides were determined by X-ray analysis.

Preparation and biodistribution of [18F]FP2OP as myocardial perfusion imaging agent for positron emission tomography

Myocardial extractions of pyridaben, a mitochondrial complex I (MC-I) inhibitor, is well correlated with blood flow. Based on the synthesis and characterization of pyridaben analogue 2-tert-butyl-5-[2-(2-[18F]fluroethoxy)ethoxy]benzyloxy]-4-chloro-2H-pyridazin-3-one ([18F]FP2OP), this study assessed its potential to be developed as myocardial perfusion imaging (MPI) agent. Methods: The tosylate labeling precursor 2-(2-(4-(tert-butyl-5-chloro-6-oxo-1,6-dihydro-pyridazin-4-yloxymethyl)benzyloxy)ethoxy)ethyl ester (OTs-P2OP) and the nonradioactive 2-tert-butyl-5-[2-(2-[19F]fluroethoxy)ethoxy]benzyloxy]-4-chloro-2H-pyridazin-3-one ([19F]FP2OP) were synthesized and characterized by IR, 1H NMR, 13C NMR and MS analysis. By substituting tosyl of precursor OTs-P2OP with 18F, the radiolabeled complex [18F]FP2OP was prepared and further evaluated for its in vitro physicochemical properties, in vivo biodistribution, the metabolic stability in mice, ex vivo autoradiography and cardiac PET/CT imaging. Results: Starting with [18F]F- Kryptofix 2.2.2./K2CO3 solution, the total reaction time for [18F]FP2OP was about 100 min, with final high-performance liquid chromatography purification included. Typical decay-corrected radiochemical yield stayed at 41 ± 5.3%, the radiochemical purity, 98% or more. Biodistribution in mice showed that the heart uptake of [18F]FP2OP was 41.90 ± 4.52%ID/g at 2 min post-injection time, when the ratio of heart/liver, heart/lung and heart/blood reached 6.83, 9.49 and 35.74, respectively. Lipophilic molecule was further produced by metabolized [18F]FP2OP in blood and urine at 30 min. Ex vivo autoradiography demonstrates that [18F]FP2OP may have high affinity with MC-I and that can be blocked by [19F]FP2OP or rotenone (a known MC-I inhibitor). Cardiac PET images were obtained in a Chinese mini-swine at 5, 15, 30 and 60 min post-injection time with high quality. Conclusion: [18F]FP2OP was synthesized with high radiochemical yield. The promising biological properties of [18F]FP2OP suggest high potential as MPI agent for positron emission tomography in the future.

Electron transfer and subsequent reactions during electrochemical oxidation of aryl- and alkylthio derivatives of mucochloric acid

The electrochemical oxidation of aryl- and alkylthio derivatives of mucochloric acid (3,4-dichloro-5-hydroxyfuran-2(5H)-one) in MeCN-Bu 4NBF4 (0.1 mol L-1) was investigated. It was shown that all sulfides are electrochemically active, from one to five oxidation steps of sulfur-containing groups were observed for them. The ease and direction of oxidation of the thio group depend on its nature and position in the furanone ring. 3-Substituted 2(5H)-furanones possess the lowest oxidation potential. 4-Substituted 2(5H)-furanones are predominantly oxidized to sulfoxides, 5-aryl- and -alkylthio derivatives undergo fragmentation to give mucochloric acid, and 3-arylthio derivative gives complex unidentified mixture of products. In the case of 3,4-bis(4-methylphenylthio) derivative, the oxidation product of the arylthio group at the 3 position to the corresponding sulfoxide was isolated. Based on the data from cyclic voltammetry with different concentrations of a substrate and water added, the results of preparative electrolysis and quantum chemical calculations, possible mechanisms of electrochemical oxidation of mucochloric acid-derived sulfides are discussed. The initial common step is a reversible single-electron transfer from the substrate molecule to form highly reactive radical cation.

Synthesis of chlorinated 5-hydroxy 4-methyl-2(5H)-furanones and mucochloric acid

An improved procedure for the synthesis of chlorinated 5-hydroxy-4-methyl-2(5H)-furanones is described. By this method also carbon-labelled (13C and 14C at C-3) hydroxyfuranones, including mucochloric acid, can be prepared. Each step of the method was examined in an effort to optimize both the yield and the purity of the compounds.