20766-36-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorobenzylideneacetone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties. Its presence in the molecular structure can influence the pharmacokinetics and pharmacodynamics of the final drug product, enhancing its efficacy and safety profile.
Used in Agrochemical Industry:
In the agrochemical sector, 3-chlorobenzylideneacetone is utilized as a building block in the creation of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the development of compounds that can effectively control pests and weeds, thereby improving crop yields and agricultural productivity.
Used in Fine Chemicals Production:
3-Chlorobenzylideneacetone is employed as a crucial component in the production of fine chemicals, which are high-purity chemicals used in various applications, including research, diagnostics, and the synthesis of other specialty chemicals. Its versatility and reactivity make it an essential precursor in the synthesis of complex organic molecules.
Used in Dyes and Pigments Industry:
This aromatic ketone is used as a building block in the manufacture of dyes and pigments, where its chemical structure contributes to the color and stability of the final product. Its presence in dye formulations can enhance colorfastness, brightness, and resistance to fading, making it suitable for various applications, such as textiles, plastics, and printing inks.
Used in Perfumery and Fragrance Industry:
3-Chlorobenzylideneacetone is utilized in the perfumery and fragrance industry as a component in the creation of unique and complex scents. Its chemical properties allow for the development of fragrances with distinct olfactory profiles, contributing to the overall sensory experience of perfumes, colognes, and other scented products.

InChI:InChI=1/C10H9ClO/c1-8(12)5-6-9-3-2-4-10(11)7-9/h2-7H,1H3/b6-5+

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 79-46-9 2-nitropropane 
• 141-97-9 ethyl acetoacetate 
• 108-42-9 3-chloro-aniline 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 78-94-4 methyl vinyl ketone 
• 1454271-81-8 C₁₀H₈ClFO 
• 3506-73-8 1-(3-chlorophenyl)butan-3-one 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 930769-45-2 (+/-)-4-(3-chlorophenyl)-2-azetidinone 
• 71-43-2 benzene 

Downstream Products

• 1055328-74-9 C₂₀H₂₁ClN₂O 
• 1055329-02-6 C₂₀H₂₁ClN₂O 
• 1055328-75-0 C₂₀H₂₁ClN₂O 
• 1194653-85-4 (1S,2S,6R)-6'-chloro-2-(3-chlorophenyl)-6-isobutylspiro[cyclohexane-1,3'-indoline]-2',4-dione 
• 1194653-92-3 (1S,2S,6R)-6'-chloro-2-(3-chlorophenyl)-6-ethylspiro[cyclohexane-1,3'-indoline]-2',4-dione 
• 1194653-93-4 (1R,2R,6S)-6'-chloro-2-(3-chlorophenyl)-6-ethylspiro[cyclohexane-1,3'-indoline]-2',4-dione 
• 132294-96-3 (R)-3-[1-(3-chlorophenyl)-3-oxobutyl]-4-hydroxy-chromen-2-one 
• 132295-91-1 (S)-3-[1-(3-chlorophenyl)-3-oxobutyl]-4-hydroxy-chromen-2-one 
• 1202448-03-0 (1S,6S,E)-tert-butyl 6-(3-chlorophenyl)-1-fluoro-4-oxo-2-styrylcyclohex-2-enecarboxylate 
• 1202448-30-3 C₂₅H₂₆ClFO₄ 
• 1201528-06-4 (R)-4-(3-chlorophenyl)-4-(4,7-dihydro-1H-indol-2-yl)butan-2-one 
• 21613-55-8 trans-1-<3-Chlor-phenyl>-but-1-en-3-on-β-oxim 
• 21613-54-7 trans-1-<3-Chlor-phenyl>-but-1-en-3-on-α-oxim 
• 1207477-75-5 ethyl 6-(3-chlorophenyl)-4-oxo-2-phenylcyclohex-2-enecarboxylate 

Relevant academic research and scientific papers

Reaction of 4-hydroxycoumarin with 2-acetyloxiranes

The reaction of 4-hydroxycoumarin with 2-acetyloxiranes in dimethylformamide in the presence of triethylamine gave 2,3-dihydro-4H-furo[3,2- c]chromen-4-ones which were converted into 4H-furo[3,2-c]-chromen-4-one derivatives as a result of dehydration or f

Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs

Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate

A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.

THIAZOLE DERIVATIVES AS PROTEIN SECRETION INHIBITORS

Provided herein are secretion inhibitors, such as inhibitors of Sec61, methods for their preparation, related pharmaceutical compositions, and methods for using the same, wherein the compound has a structure of Formula (I), (II), or (III).

Dehydrozingerone Inspired Discovery of Potential Broad-Spectrum Fungicidal Agents as Ergosterol Biosynthesis Inhibitors

A series of dehydrozingerone derivatives were synthesized, and their fungicidal activities and action mechanism against Colletotrichum musae were evaluated. The bioassay result showed that most compounds exhibited excellent fungicidal activity in vitro at 50 μg mL-1. Compounds 13, 16, 18, 19, and 27 exhibited broad-spectrum fungicidal activity; especially, compounds 19 and 27 were found to have more potent fungicidal activity than azoxystrobin. The EC50 values of compounds 19 and 27 against Rhizoctonia solani were 0.943 and 0.161 μg mL-1 respectively. Moreover, compound 27 exhibited significant in vitro bactericidal activity against Xanthomonas oryzae pv. oryzae, with an EC50 value of 11.386 μg mL-1, and its curative effect (49.64%) and protection effect (51.74%) on rice bacterial blight disease was equivalent to that of zhongshengmycin (42.90%, 40.80% respectively). Compound 27 could also effectively control gray mold (87.10%, 200 μg mL-1) and rice sheath blight (100%, 200 μg mL-1 82.89%, 100 μg mL-1) in vivo. Preliminary action mechanism study showed that compound 27 mainly acted on the cell membrane and significantly inhibited ergosterol biosynthesis in Colletotrichum musae.

Dehydrozingerone derivative and preparation method and application thereof

The invention provides a dehydrozingerone derivative as shown in the description. R-R are each independently selected from hydrogen or halogen or a nitro group or an alkyl group or a substitutedalkoxy group or an alkoxy group or a hydroxyl group; the substituent in the substituted alkoxy group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; R and R areeach independently selected from hydrogen or halogen or nitrogen-containing heterocycle; R is selected from an alkyl group or an alkoxy group or a substituted alkoxy group; the substituent in thesubstituted alkyl group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; X is selected from a hetero atom or a hydroxylamine group. The dehydrozingerone derivative hasbroad-spectrum activity against plant pathogenic fungi and bacteria, and has certain nematicidal activity, and is a lead compound with the broad biological activity.

Enantioselective Copper-Catalyzed 1,5-Cyanotrifluoromethylation of Vinylcyclopropanes

A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the in situ generated CF3 radical from Togni's reagent, this method offers a new solution for remote enantioselective bifunctionalization of alkenes and thus provides a straightforward way for the synthesis of chiral CF3-containing internal alkenylnitriles.

Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).

Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3-Diols

A chemo- and biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3-diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β-borylation of α,β-unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol compounds were then bioreduced by yeasts. The biotransformation set up with Rhodotorula rubra allowed (R)-keto–alcohols and (S,S)-diols to be obtained with up to 99 % ee and up to 99 % de in favor of the anti enantiomers.