5809-92-7

Basic information

• Product Name: (5E)-5-(2,5-dimethoxybenzylidene)-1-phenylpyrimidine-2,4,6(1H,3H,5H)-trione
• CAS NO: 5809-92-7
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 352.3407
• Mol File: 5809-92-7.mol
• Article Data: 4

Chemical Properties

• Density: 1.339g/cm³
• Refractive Index: 1.635
• CAS DataBase Reference: (5E)-5-(2,5-dimethoxybenzylidene)-1-phenylpyrimidine-2,4,6(1H,3H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-5-(2,5-dimethoxybenzylidene)-1-phenylpyrimidine-2,4,6(1H,3H,5H)-trione(5809-92-7)
• EPA Substance Registry System: (5E)-5-(2,5-dimethoxybenzylidene)-1-phenylpyrimidine-2,4,6(1H,3H,5H)-trione(5809-92-7)

Safety Data

• Hazardous Substances Data: 5809-92-7(Hazardous Substances Data)

Upstream product

• 109-99-9 tetrahydrofuran 
• 20452-67-9 phenylethylketene 
• 675825-21-5 Lithium enolate of the acetaldehyde 
• 108-05-4 vinyl acetate 
• 90-27-7 2-Phenylbutyric acid 
• 105-38-4 vinyl propionate 

Downstream Products

• 75-07-0 acetaldehyde 

Relevant articles and documents

Model Studies on the Enzyme-Regulated Stereodivergent Cascade Passerini Reaction

The synthesis of chiral α-acyloxy carboxamides containing two stereogenic centers continues to be a challenging field of organic chemistry. Herein, we have proposed and proved the feasibility of an enzyme regulated-cascade reaction, which using the same substrates enables the formation of individual stereoisomers of α-acyloxy carboxamides with up to 99 % ee. The access to the individual stereoisomeric products has been achieved by a combination of the enzymatic kinetic resolution of racemic vinyl esters, subsequent Passerini reaction, and enzymatic kinetic resolution of formed α-acyloxy carboxamides. The presented studies are promising in exploratory proof-of-concept of enzyme-controlled stereodivergent cascade to form an important class of chiral compounds for medicinal chemistry.

Nucleophilic Additions to Ketenes by (Trimethylsilyl)lithium and by Enolates

Reaction of t-Bu2C=C=O (5) with Me3SiLi at -78 deg C followed by trapping of the intermediate enolate with Ac2O gave t-Bu2C=C(OAc)SiMe3 (9).Other ketenes gave similar products.Reaction of ketenes PhCR=C=O (R = Me, 13; R = Et, 3) with enolates CH2=C(OLi)R1 (R1 = H, Me, t-Bu, Ph) at -78 deg C followed by warming to 25 deg C and hydrolysis gave vinyl esters PhCHRCO2C(R1)=CH2, along with 10 percent PhCHMeCOCH2COPh for R = Me, R1 = Ph.Under the same conditions the ketenes PhCR=C=O with enolates CH2=C(OK)R1 (R1 = Me, t-Bu, Ph) gave only 1,3-diketones PhCHRCOCH2COR1, but vinyl esters were the major products if the reactions were quenched at -78 deg C.It is proposed that enolates undergo preferential O-acylation by ketenes in a kinetically favored process, but that these intermediates can revert to thermodynamically more stable C-acylated products.