55628-85-8

Basic information

• Product Name: 1-Imidazol-1-yl-5-phenyl-pentan-1-one
• Synonyms: 1-Imidazol-1-yl-5-phenyl-pentan-1-one
• CAS NO: 55628-85-8
• Molecular Weight: 228.294
• Mol File: 55628-85-8.mol

Chemical Properties

• CAS DataBase Reference: 1-Imidazol-1-yl-5-phenyl-pentan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Imidazol-1-yl-5-phenyl-pentan-1-one(55628-85-8)
• EPA Substance Registry System: 1-Imidazol-1-yl-5-phenyl-pentan-1-one(55628-85-8)

Safety Data

• Hazardous Substances Data: 55628-85-8(Hazardous Substances Data)

Upstream product

• 2270-20-4 5-Phenylpentanoic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1086277-70-4 N₁-(5-phenylpentanoyl)-N₂-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine 
• 235087-22-6 7-phenyl-3-trifluoromethanesulfonyloxy-hept-2-enoic acid tert-butyl ester 
• 100848-88-2 6-Phenyl-1-hexyne 
• 189030-32-8 tert-butyl 3-oxo-7-phenylheptanoate 

Relevant articles and documents

Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes

Direct synthetic routes to amidines are desired, as they are widely present in many biologically active compounds and organometallic complexes. N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper-catalyzed three-component reaction of aryl acetylenes, amines, and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO2 as the only byproduct. Transformation of the dioxazolones on the Cu catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu-C bond rather than undergoing an undesired Curtius rearrangement. For nonaromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 min. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple copper(I) iodide (CuI) as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol %. The herein reported procedure not only provides a new, practical, and direct route to N-acyl amidines but also represents a new type of C-N bond formation.

Development of New Benzylpiperazine Derivatives as σ1Receptor Ligands with in Vivo Antinociceptive and Anti-Allodynic Effects

σ-1 receptors (σ1R) modulate nociceptive signaling, driving the search for selective antagonists to take advantage of this promising target to treat pain. In this study, a new series of benzylpiperazinyl derivatives has been designed, synthesized, and characterized for their affinities toward σ1R and selectivity over the σ-2 receptor (σ2R). Notably, 3-cyclohexyl-1-{4-[(4-methoxyphenyl)methyl]piperazin-1-yl}propan-1-one (15) showed the highest σ1R receptor affinity (Ki σ1 = 1.6 nM) among the series with a significant improvement of the σ1R selectivity (Ki σ2/Ki σ1 = 886) compared to the lead compound 8 (Ki σ2/Ki σ1 = 432). Compound 15 was further tested in a mouse formalin assay of inflammatory pain and chronic nerve constriction injury (CCI) of neuropathic pain, where it produced dose-dependent (3-60 mg/kg, i.p.) antinociception and anti-allodynic effects. Moreover, compound 15 demonstrated no significant effects in a rotarod assay, suggesting that this σ1R antagonist did not produce sedation or impair locomotor responses. Overall, these results encourage the further development of our benzylpiperazine-based σ1R antagonists as potential therapeutics for chronic pain.

Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones

Single-electron N-heterocyclic carbene (NHC) catalysis has gained attention recently for the synthesis of C?C bonds. Guided by density functional theory and mechanistic analyses, we report the light-driven synthesis of aliphatic and α-amino ketones using single-electron NHC operators. Computational and experimental results reveal that the reactivity of the key radical intermediate is substrate-dependent and can be modulated through steric and electronic parameters of the NHC. Catalyst potential is harnessed in the visible-light driven generation of an acyl azolium radical species that undergoes selective coupling with various radical partners to afford diverse ketone products. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine h2 receptor agonists

N1-Aryl(heteroaryl)alkyl-N2-[3-(1H-imidazol-4-yl) propyl]guanidines are potent histamine H2-receptor (H2R) agonists, but their applicability is compromised by the lack of oral bioavailability and CNS penetration. To improve pharmacokinetics, we introduced carbonyl instead of methylene adjacent to the guanidine moiety, decreasing the basicity of the novel H2R agonists by 4-5 orders of magnitude. Some acylguanidines with one phenyl ring were even more potent than their diaryl analogues. As demonstrated by HPLC-MS, the acylguanidines (bioisosteres of the alkylguanidines) were absorbed from the gut of mice and detected in brain. In GTPase assays using recombinant receptors, acylguanidines were more potent at the guinea pig than at the human H2R. At the hH1R and hH3R, the compounds were weak to moderate antagonists or partial agonists. Moreover, potent partial hH4R agonists were identified. Receptor subtype selectivity depends on the imidazolylpropylguanidine moiety (privileged structure), opening an avenue to distinct pharmacological tools including potent H4R agonists.

Decarboxylative elimination of enol triflates as a general synthesis of acetylenes

Decarboxylative elimination of a range of enol triflates of β-keto esters gives acetylenes.

Xanthene derived potent nonpeptidic inhibitors of recombinant human calpain I

Novel and potent, xanthene derived reversible aldehyde (7c) and α- ketocarboxamide (10a), and irreversible fluoromethyl ketone (10b) inhibitors of recombinant human calpain I are described.