627546-31-0

Basic information

• Product Name: 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone
• Synonyms: 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone
• CAS NO: 627546-31-0
• Molecular Weight: 369.403
• Mol File: 627546-31-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone(627546-31-0)
• EPA Substance Registry System: 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone(627546-31-0)

Safety Data

• Hazardous Substances Data: 627546-31-0(Hazardous Substances Data)

Upstream product

• 54582-33-1 1,1'-carbonyldiimidazole 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 19493-09-5 Methylenetriphenylphosphorane 
• 603-35-0 triphenylphosphine 
• 95525-44-3 N-chloroacetyl pyrrole 

Downstream Products

• 1021867-76-4 (2E,4E)-5-phenyl-1-(1H-pyrrol-1-yl)penta-2,4-dien-1-one 
• 1021867-77-5 (2E)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-pyrrol-1-yl-2-propen-1-one 
• 1201761-99-0 C₁₄H₁₃NO₂ 
• 1448857-55-3 (S)-1-(1H-pyrrol-1-yl)-3-(p-tolyl)butan-1-one 
• 1448857-54-2 3-(3-isopropylphenyl)-1-(1H-pyrrol-1-yl)butan-1-one 
• 1448857-53-1 (E)-3-(3-isopropylphenyl)-1-(1H-pyrrol-1-yl)prop-2-en-1-one 
• 627546-39-8 (2S,3R)-trans-2,3-epoxy-5-(4-methoxybenzyloxy)-1-pyrrol-1-yl-pentan-1-one 
• 627546-50-3 (R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one 

Relevant articles and documents

α,β-unsaturated N-Acylpyrrole peptidyl derivatives: New proteasome inhibitors

Because of the encouraging results obtained using vinyl ester derivatives, we synthesized and tested a novel series of peptide-based proteasome inhibitors bearing a new pharmacophore unit at the C-terminal. N-Acylpyrrole moiety is a potential substrate for Michael addition by catalytic threonine. Several analogues have demonstrated a selective inhibition of the multicatalytic complex β1 subunits, the capacity to permeate cellular membrane, and good pharmacokinetics properties.

Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors

Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors is described. A Sm(O-i-Pr)3/(R)-H8-BINOL complex promoted the epoxidation reaction to afford products in high yield (up to quant) and high enantiomeric excess (up to >99.5% ee). Reaction proceeded smoothly using cumene hydroperoxide (CMHP) with low explosive hazard, and completed within 0.2-0.5 h with 5 mol % catalyst. Catalyst loading was successfully reduced to as little as 0.02 mol %. The N-acylpyrrole properties as well as efficient synthesis of α,β-unsaturated N-acylpyrroles are also described.

Sequential Wittig olefination-catalytic asymmetric epoxidation with reuse of waste Ph3P(O): Application of α,β-unsaturated N-Acyl pyrroles as ester surrogates

Waste not, want not: Efficient one-pot access to optically active epoxides with 96 to 99.5% ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by-product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated N-acyl pyrrole Wittig product (see scheme). The N-acyl pyrrole functionality is key to the high reactivity and selectivity observed. R = alkyl, aryl, vinyl.