1,5-DIHYDRO-PYRROL-2-ONE

Base Information

• Chemical Name: 1,5-DIHYDRO-PYRROL-2-ONE
• CAS No.: 4031-15-6
• Molecular Formula: C4H5 N O
• Molecular Weight: 83.0898
• Hs Code.: 2933990090
• Mol file: 4031-15-6.mol

Synonyms:3-Pyrrolin-2-one(6CI,7CI,8CI); 1H-Pyrrole-2(5H)-one; 2,5-Dihydropyrrol-2-one; 2-Butenoic acid,4-amino-, lactam

Chemical Property of 1,5-DIHYDRO-PYRROL-2-ONE

Chemical Property:

• Melting Point: 140 °C
• Boiling Point: 292.2±23.0 °C(Predicted)
• PKA: 14.35±0.20(Predicted)
• PSA: 29.10000
• Density: 1.114±0.06 g/cm3(Predicted)
• LogP: 0.00120
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-Pyrrolin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-Pyrrolin-2-one is an oxo analogue and oxidation product of pyrrole.

Technology Process of 1,5-DIHYDRO-PYRROL-2-ONE

There total 9 articles about 1,5-DIHYDRO-PYRROL-2-ONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

maleiimide (541-59-3,25721-74-8) → 3-pyrrolin-2-one (4031-15-6)

Guidance literature:

With trifluorormethanesulfonic acid; cyclohexane; antimony pentafluoride; at 25 ℃; for 0.166667h;

DOI:10.1002/ejoc.200600486

Reference yield: 80.0%

1-(perfluorobenzoyl)pyrrolidin-2-one → 3-pyrrolin-2-one (4031-15-6)

Guidance literature:

With palladium(II) trifluoroacetate; racemic methyl phenyl sulfoxide; di-n-butylboryl trifluoromethanesulfonate; 2,5-di-tert-butyl-p-benzoquinone; zinc(II) trifluoroacetate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; at 20 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.7b04722

Reference yield: 63.0%

C16H14N2O → 3-pyrrolin-2-one (4031-15-6)

Guidance literature:

In hexane; toluene; for 10h; Inert atmosphere; UV-irradiation;

DOI:10.1055/s-0029-1217759

upstream raw materials:

methyl (E)-4-(1,3-dioxoisoindolin-2-yl)but-2-enoate

pyrrole

maleiimide

N-(prop-2-en-1-yl)prop-2-enamide

Downstream raw materials:

(Z)-2,2'-pyrromethene-5<1H>-one

N-(tert-butoxycarbonyl)pyrrol-2(5H)-one

5-(2,6-Dihydroxy-4-pentylphenyl)pyrrolidin-2-one

5-(5-Benzyloxy-1H-indol-3-yl)pyrrolidin-2-one

Refernces

New ring expansion of cyclobutanones: Synthesis of pyrrolinones, pyrrolidines and pyrroles

10.1055/s-2004-822900

The research explores a novel method for expanding the ring structure of cyclobutanones to synthesize various five-membered azaheterocyclic compounds, including pyrrolinones, pyrrolidines, and pyrroles. The study aims to develop an efficient and high-yielding synthetic pathway for these heterocycles, which are known for their significant physiological and pharmacological properties. The researchers used 2,2-dichlorocyclobutanones as starting materials, reacting them with amines to induce ring opening, forming 4,4-dichlorobutanamides. These intermediates were then converted into enol ethers using sodium methoxide, which were subsequently cyclized to form 3-pyrrolin-2-ones by treatment with aqueous HCl. The synthesized pyrrolinones were further reduced to pyrrolidinones and pyrrolidines using hydrogen on palladium and LiAlH4, respectively. Additionally, the pyrrolinones were converted to pyrroles using 9-borabicyclo[3.3.1]nonane (9-BBN). The study concludes that this new ring expansion method provides an efficient and versatile route for synthesizing a variety of physiologically active azaheterocyclic compounds, offering good yields and scalability.