128947-01-3

Basic information

• Product Name: (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone
• Synonyms: (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone
• CAS NO: 128947-01-3
• Molecular Weight: 258.32
• Mol File: 128947-01-3.mol

Chemical Properties

• CAS DataBase Reference: (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone(128947-01-3)
• EPA Substance Registry System: (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone(128947-01-3)

Safety Data

• Hazardous Substances Data: 128947-01-3(Hazardous Substances Data)

Upstream product

• 24221-86-1 (+)-(1S,2R)-ephedrine hydrochloride 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 10487-71-5 crotonyl chloride 
• 625-35-4 trans-chrotonyl chloride 

Downstream Products

• 128863-72-9 (4R,5S)-1,5-Dimethyl-3-((R)-3-methyl-hex-5-enoyl)-4-phenyl-imidazolidin-2-one 
• 183074-26-2 (4R,5S)-1,5-Dimethyl-3-((2S,3R)-3-methyl-aziridine-2-carbonyl)-4-phenyl-imidazolidin-2-one 
• 176791-95-0 (4R,5S)-1,5-Dimethyl-3-((2R,3S)-3-methyl-aziridine-2-carbonyl)-4-phenyl-imidazolidin-2-one 
• 331283-98-8 (4R,5S)-1,5-dimethyl-3-[(1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-en-2-ylcarbonyl]-4-phenyl-2-imidazolidinone 
• 139962-49-5 (4R,5S)-1,5-Dimethyl-4-phenyl-3-((S)-3-p-tolyl-butyryl)-imidazolidin-2-one 
• 113675-84-6 (4R,5S)-1,5-Dimethyl-4-phenyl-3-((S)-3-phenyl-butyryl)-imidazolidin-2-one 
• 113675-86-8 (4R,5S)-1,5-Dimethyl-4-phenyl-3-((R)-3-phenyl-butyryl)-imidazolidin-2-one 
• 139962-60-0 (4S,5R)-1-((S)-3,5-Dimethyl-hex-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 139962-60-0 (4S,5R)-1-((R)-3,5-Dimethyl-hex-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 139962-59-7 (4S,5R)-1-((S)-3,4-Dimethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 139962-59-7 (4S,5R)-1-((R)-3,4-Dimethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 139962-66-6 (4R,5S)-1,5-Dimethyl-3-((S)-3-methyl-pent-4-enoyl)-4-phenyl-imidazolidin-2-one 
• 139962-58-6 (4R,5S)-1,5-Dimethyl-3-((R)-3-methyl-pent-4-enoyl)-4-phenyl-imidazolidin-2-one 
• 139962-52-0 (4R,5S)-1,5-Dimethyl-3-((R)-3-methyl-hexanoyl)-4-phenyl-imidazolidin-2-one 

Relevant articles and documents

A novel method for the N-acylation of (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one

An efficient synthesis of N-Acylimidazolidinones derived from α,β-unsaturated acid chlorides using DABCO as the base is described.

N-Alkenoylimidazolidin-2-ones as chiral dienophiles in Diels-Alder cycloaddition reactions

Homochiral N-enoylimidazolidin-2-ones 5-8 are readily accessible, practical, and highly diastereoselective dienophiles in dialkylaluminium-promoted Diels-Alder reactions. Acrylate, methacrylate, and (E)-crotonate derivatives bearing ephedrine-based imidaz

Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral α,β-unsaturated N-acyl imidazolidinones

The organocopper-Lewis acid system, RCu-TMEDA-Bu2BOTf, is useful for conjugate addition to highly constrained chiral α,β-unsaturated N-acyl imidazolidinones. In comparison with the corresponding TMSCl-activated reagents, Bu2BOTf exhi

Asymmetric 1,4-addition of Grignard reagents to chiral α,β-unsaturated imides in the presence of Lewis acids

The asymmetric 1,4 addition of PhMgCl, MeMgBr and allylMgBr to chiral imides 1 has been studied under various conditions. The presence of a Lewis acid, as AlMe2Cl, affords an enhanced diastereoselectivity favouring the formation of the product derived from the attack on the re face. The 1,4 addition of allyl diisopropoxyborate to imides 1 has also been analysed.

Diastereoselective additions of alkyl, akenyl, aryl and allyl cuprates to unsaturated chiral imides

Some diastereoselective conjugate additions of cuprates to chiral unsaturated imides bearing an imidazolidinyl group (from ephedrine and urea) show an impressive stereoselectivity. The chiral (internal auxiliary dependent) group is easily broken and recyc

Imidazolidin-2-ones as Practical, Efficient Chiral Auxiliaries in Diels-Alder Reactions

The readily prepared (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one and its 4-cyclohexyl analogue proved to be very powerful face-selective auxiliaries in catalysed Diels-Alder cycloadditions of their α,β-unsaturated N-acyl dienophile derivatives.