30625-58-2

Basic information

• Product Name: (E)-4-(4-dimethylaminophenyl)but-3-en-2-one
• Synonyms: (E)-4-(4-dimethylaminophenyl)but-3-en-2-one;4-(4-(Dimethylamino)phenyl)-3-buten-2-one
• CAS NO: 30625-58-2
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.2536
• Mol File: 30625-58-2.mol

Chemical Properties

• Melting Point: 134 °C(Solv: benzene (71-43-2); methanol (67-56-1)(95:5))
• Boiling Point: 340.6°Cat760mmHg
• Flash Point: 132.6°C
• Appearance: /
• Density: 1.039g/cm³
• PKA: 4.88±0.24(Predicted)
• CAS DataBase Reference: (E)-4-(4-dimethylaminophenyl)but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(4-dimethylaminophenyl)but-3-en-2-one(30625-58-2)
• EPA Substance Registry System: (E)-4-(4-dimethylaminophenyl)but-3-en-2-one(30625-58-2)

Safety Data

• Hazardous Substances Data: 30625-58-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 3073, 1948 DOI: 10.1021/ja01189a069

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 4743-82-2 4-oxo-2-pentenoic acid 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 

Downstream Products

• 69045-27-8 7t-phenyl-1t-(4-dimethylamino-phenyl)-heptatrien-(1.4t.6)-one-⁽³⁾ 
• 34292-27-8 4t-(4-dimethylamino-phenyl)-but-3-en-2-one-phenylhydrazone 
• 101717-70-8 4-(4-(dimethylamino)phenyl)-4-phenylbutan-2-one 
• 120049-61-8 4-(4'-dimethylaminophenyl)-2-butanol 
• 55420-64-9 3-bromo-4-(4-dimethylamino-phenyl)-but-3-en-2-one 
• 29208-42-2 (E)-1-Diazo-4-(4-dimethylamino-phenyl)-but-3-en-2-one 
• 932022-17-8 6-[2-(4-N,N-dimethylaminophenyl)vinyl]-4-methylthio-2-oxo-2H-pyran-3-carbonitrile 

Relevant articles and documents

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.

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

Enantioselective NiH/Pmrox-Catalyzed 1,2-Reduction of α,β-Unsaturated Ketones

The enantioselective 1,2-reduction of α,β-unsaturated ketones was achieved using a NiH catalyst in the presence of pinacolborane. This mild process represents a general method to access a wide variety of structurally diverse α-chiral allylic alcohols in excellent yields and enantioselectivity, as well as very high levels of ambidoselectivity for 1,2- over 1,4-reduction. Furthermore, for reactions on a 10 mmol scale, catalyst loadings as low as 0.5 mol % could be employed to deliver product without any detrimental effect on the yield, enantio-, or ambidoselectivity.

Br?nsted Acid Catalyzed Homoconjugate Addition of Organotrifluoroborates to Arylated Cyclopropyl Ketones

A novel and practical homoconjugate addition of alkenyl, alkynyl, heteroaryl, and aryl trifluoroborates to arylated cyclopropyl ketones to synthesize γ,γ-disubstituted ketones is reported. A preliminary mechanistic proposal involving ketone protonation, a

A promiscuous de Novo retro-aldolase catalyzes asymmetric michael additions via Schiff base intermediates

Recent advances in computational design have enabled the development of primitive enzymes for a range of mechanistically distinct reactions. Here we show that the rudimentary active sites of these catalysts can give rise to useful chemical promiscuity. Sp

Palladium-catalyzed conjugate addition of arylsulfonyl hydrazides to α,β-unsaturated ketones

A palladium-catalyzed desulfitative-denitrogenative conjugate addition of arylsulfonyl hydrazides to α,β-unsaturated ketones is described. The reaction showed very good selectivity and tolerated a wide range of functionalities under an atmosphere of oxygen with or without the aid of a metal co-oxidant. The Royal Society of Chemistry 2013.

Palladium-catalyzed decarboxylative arylation of benzoylacrylic acids toward the synthesis of chalcones

It has been found that readily available 3-benzoylacrylic acids undergo palladium-catalyzed decarboxylative arylation with arylboronic acids in the presence of a copper salt oxidant to produce chalcone derivatives. The decarboxylative arylation could also be achieved using aryl halides as the alternative aryl source to expand the applicable scope.

Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas

A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

First bovine serum albumin-promoted synthesis of enones, cinnamic acids and coumarins in ionic liquid: An insight into the role of protein impurities in porcine pancreas lipase for olefinic bond formation

During studies on exploiting the catalytic promiscuity of crude porcine pancreas lipase (PPL) in ionic liquid for C=C bond formations, bovine serum albumin (BSA) was found to be competing for these reactions. After a detailed investigation, we establish that these transformations are possible by unspecific protein catalysis rather than catalytic promiscuity of "PPL" - a first insight into the role of protein impurities in crude enzyme. Thus, a novel and highly efficient, environmentally friendly approach involving synergistic catalysis by bovine serum albumin-1-butyl-3- methylimidazolium bromide (BSA-[bmim]Br) has been developed for the synthesis of (E)-α,β-unsaturated compounds including a one-pot cascade synthesis of cinnamic acids and coumarins via aldol, Knoevenagel and Knoevenagel-Doebner condensations.

Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for ?-Amyloid Plaques

A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A1-42 aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two 18F fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity for A1-42 aggregates (Ki ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for β-amyloid imaging probes.