583-05-1

Usage

Uses

1-Phenyl-1,4-pentanedione is used as an organic chemical synthesis intermediate.

Synthesis Reference(s)

Chemistry Letters, 25, p. 633, 1996The Journal of Organic Chemistry, 48, p. 2608, 1983 DOI: 10.1021/jo00163a040

InChI:InChI=1/C11H12O2/c1-9(12)7-8-11(13)10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

Upstream product

• 52313-43-6 3-acetyl-1-phenyl-pentane-1,4-dione 
• 58193-48-9 1-phenyl-1-hydroxy-pentane-4-one 
• 130850-70-3 2-acetyl-4-oxo-4-phenyl-butyric acid 
• 99853-91-5 4-chloro-1-phenyl-pent-3-en-1-one 
• 123-76-2 levulinic acid 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 53626-81-6 4-Chloro-1-phenyl-pent-4-en-1-one 
• 56418-13-4 4-bromo-1-phenylpent-4-en-1-one 
• 141-97-9 ethyl acetoacetate 
• 70-11-1 α-bromoacetophenone 
• 100-52-7 benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 2543-57-9 1-Dimethylamino-3-butanon 

Downstream Products

• 33553-32-1 4-methyl-1-phenyl-carbazole 
• 3810-26-2 3-phenyl-2-cyclopenten-1-one 
• 7063-98-1 3-acetyl-5-phenyl-isoxazole 
• 34671-15-3 3-benzoyl-5-methylisoxazole 
• 34721-89-6 2-methyl-5-phenyl-furan 
• 132726-49-9 1-(3-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole 
• 132726-50-2 1-(2-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole 
• 132726-51-3 1-(4-methoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole 
• 26180-27-8 1-<2-Carboxy-phenyl>-2-methyl-5-phenyl-pyrrol 
• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 
• 146204-41-3 2-methyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrrole 
• 3771-57-1 2-methyl-1,5-diphenyl-1H-pyrrole 
• 93315-44-7 2-(2-methyl-5-phenyl-pyrrol-1-yl)-phenol 
• 108979-47-1 3-(2-methyl-5-phenyl-pyrrol-1-yl)-phenol 

Relevant academic research and scientific papers

Photoredox-Catalyzed Generation of Acetonyl Radical in Flow: Theoretical Investigation and Synthetic Applications

A hydrogen atom transfer (HAT) step from acetone allowed the smooth generation of acetonyl radical that was then exploited as synthon in the mild formation of C-C bonds under flow conditions. The process was promoted by aryl radicals photocatalytically generated via single-electron transfer (SET) reduction of arenediazonium salts. The mechanism has been investigated by a combined experimental and computational approach and further supported by deuterium labeling experiments.

Study on the interaction of 1,5-diaryl pyrrole derivatives with αglucosidase; synthesis, molecular docking, and kinetic study

Background: The delaying of absorption of glucose is one of the principal therapeutic approaches of type 2 diabetes. α-glucosidase inhibitors compete with the α-glucosidase enzyme activity, which helps to reduce the conversion of carbohydrates into glucose and thereby control the postprandial hyperglycemia incidence. Objective: The aim of this study was to synthesize a series of novel 1,5-diphenyl pyrrole derivatives and evaluate their in vitro α-glucosidase inhibitory activities. Methods: Compounds were synthesized through a multistep reaction and were evaluated for αglucosidase inhibitory activities. Molecular docking and kinetic studies were carried out to predict the mode of binding and mechanism of inhibition for the most active compounds, 5g and 5b, against α-glucosidase. Results: Synthesized compounds showed good in vitro α-glucosidase inhibitory activity with IC50 values in the range of (117.5 ± 3.8 to 426.0 ± 10.2 μM) as compared to acarbose, the standard drug, (750 ± 8.7 μM). Compound 5g (117.5 ± 3.8 μM) ascertained as the most potent inhibitor of α-glucosidase in a competitive mode. The binding energies of compounds 5g and 5b (119.0 ± 7.5 μM), as observed from the best docking conformations, indicate that they have a lower free binding energy (-3.26 kcal/mol and-3.0 kcal/mol, respectively) than acarbose (2.47 kcal/mol). Conclusion: The results of our study revealed that the synthesized compounds are a potential candidate for α-glucosidase inhibitors for the management of postprandial hyperglycemia for further investigation.

Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction

Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

Dibromo-BODIPY as an Organic Photocatalyst for Radical-Ionic Sequences

A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)3Cl2, one of the most common photocatalysts in a known radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the generated oxonium ion is trapped by an internal nucleophile were developed using this BODIPY photocatalyst. These new sequences allowed the straightforward preparation of ?3-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans. This new catalyst, the methodology, and the forged functional groups could be important tools in organic synthesis.

Synthesis and biological evaluation of 2-(2-methyl-1H-pyrrol-3-yl)-2-oxo-N-(pyridine-3-yl) acetamide derivatives: in vitro α-glucosidase inhibition, and kinetic and molecular docking study

One of the therapeutic approaches in the management of type 2 diabetes is delaying the glucose absorption through α-glucosidase enzyme inhibition, which can reduce the occurrence of postprandial hyperglycemia. Based on this thought, a series of novel chloro-substituted 2-(2-methyl-1-phenyl-1H-pyrrol-3-yl)-2-oxo-N-(pyridin-3-yl) acetamide derivatives 5a–i were synthesized and their α-glucosidase inhibitory activities were evaluated. All the synthesized compounds have shown moderate to excellent in vitro α-glucosidase inhibitory activity with IC50 values in the range of 111–673?μM) as compared to acarbose, the standard drug (750 ± 9?μM). Compound 5e (111 ± 12?μM), among the series, was the most potent inhibitor of α-glucosidase in a competitive mode of action based on the kinetic study. The molecular docking study of compounds 5e and 5a revealed that they have a lower free binding energy (? 4.27?kcal/mol and ? 3.17?kcal/mol, respectively) than acarbose (? 2.47?kcal/mol), which indicates that the target compound binds more easily to the enzyme than acarbose does. The outcomes from the molecular docking studies supported the results obtained from the in vitro assay. In conclusion, the overall results of our study reveal that the synthesized compounds could be a potential candidate in the search for novel α-glucosidase inhibitors to manage postprandial hyperglycemia incidence.

Design, synthesis and in-vitro anti-cancer evaluation of novel derivatives of 2-(2-methyl-1,5-diaryl-1h-pyrrol-3-yl)-2-oxo-n-(pyridin-3-yl)acetamide

Objective: Several anti-tubulin agents were introduced for the cancer treatment so far. Despite successes in the treatment of cancer, these agents cause toxic side effects, including peripheral neuropathy. Comparing anti-tubulin agents, indibulin seemed to cause minimal peripheral neuropathy, but its poor aqueous solubility and other potential clinical problems have led to its remaining in a preclinical stage. Methods: Herein, indibulin analogues were synthesized and evaluated for their in vitro anti-cancer activity using MTT assay (on the MCF-7, T47-D, MDA-MB231 and NIH-3T3 cell lines), annexin V/PI staining assay, cell cycle analysis, anti-tubulin assay and caspase 3/7 activation assay. Results: One of the compounds, 4a, showed good anti-proliferative activity against MCF-7 cells (IC50: 7.5 μM) and low toxicity on a normal cell line (IC50 > 100μM). All of the tested compounds showed lower cytotoxicity on normal cell line in comparison to reference compound, indibulin. In the annexin V/PI staining assay, induction of apoptosis in the MCF-7 cell line was observed. Cell cycle analysis illustrated an increasing proportion of cells in the sub-G-1 phase, consistent with an increasing proportion of apoptotic cells. No increase in G2/M cells was observed, consistent with the absence of anti-tubulin activity. A caspase 3/7 assay protocol showed that apoptosis induction by more potent compounds was due to activation of caspase 3. Conclusion: newly synthesized compounds exerted acceptable anticancer activity and further investigation of current scaffold would be beneficial.

A fluorescent target-guided Paal-Knorr reaction

It has become increasingly apparent that high-diversity chemical reactions play a significant role in the discovery of bioactive small molecules. Here, we describe an expanse of this paradigm, combining a ‘target-guided synthesis’ concept with Paal-Knorr chemistry applied to the preparation of fluorescent ligands for human prostaglandin-endoperoxide synthase (COX-2).