95530-58-8

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C6H11NO2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m0/s1

Upstream product

• 75-44-5 phosgene 
• 16369-05-4 valinol 
• 14441-94-2 4-methoxy-1,3-oxazolidin-2-one 
• 920-39-8 isopropylmagnesium bromide 
• 201230-82-2 carbon monoxide 
• 103723-69-9 3-hydroxy-4-isopropyloxazolidin-2-one 
• 105-58-8 Diethyl carbonate 
• 13639-42-4 2-isopropyl-aziridine 
• 124-38-9 carbon dioxide 
• 2026-48-4 (S)-valinol 
• 13893-45-3 valine ethyl ester 
• 57-13-6 urea 
• 17016-83-0 4-isopropyloxazolidin-2-one 
• 79069-14-0 tert-butyl [(1R)-1-(hydroxymethyl)-2-methylpropyl]carbamate 

Downstream Products

• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 16369-05-4 valinol 
• 214492-01-0 (4S,2'S)-4-isopropyl-3-(2'-phenylpropanoyl)oxazolidin-2-one 
• 311310-18-6 (4S,2'R)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one 
• 96837-44-4 (R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one 
• 136436-80-1 (4S)-3-<(s'S)-2'-(4-isobutylphenyl)propanoyl>-4-(1-methylethyl)-2-oxazolidinone 
• 914222-93-8 3-(4-acetylphenyl)-4-isopropyloxazolidin-2-one 

Relevant academic research and scientific papers

Simple preparation method of N-acyl compound

The invention relates to a simple preparation method of an N-acyl compound. The simple preparation method comprises the specific steps that an amine compound and R-OCF3 are mixed in a solvent and react for 1 min-48 h at -80-100 DEG C, after the reaction is completed, water is added for quenching, and column separation and purification or recrystallization and purification are carried out to obtainthe N-acyl compound. According to the simple preparation method of the N-acyl compound, the characteristic that a substance containing trifluorooxygen groups can be decomposed in situ to produce fluorophosgene is utilized, and the substance directly reacts with the amine compound to achieve rapid N-carbonylation of an amines substrate and efficiently prepare a urea derivative and a carbamyl fluoride compound. The simple preparation method of the N-acyl compound has the advantages that the operation is simple, the reaction time is short, the application range of the substrate is wide, no catalysts or additives need to be used, the raw materials are easy to obtain, the product yield is high, the purification is easy, and the required compound can be obtained by using a column chromatographyisolation method or recrystallization.

Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3

Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.

Synthetic method and application of chiral compound

The invention relates to a synthetic method of a chiral compound. The synthetic method comprises the following steps: taking 0.2720g of zinc chloride as a catalyst under water-free and oxygen-free conditions, weighing 2.0449g of acetylurea and 8.1397g of

Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: Synthesis of (+)-1,4-dideoxyallonojirimycin

Room temperature E1cB N-N cleavage of oxazolidinone hydrazides via N-alkylation with diethyl bromomalonate and potassium or caesium carbonate as base in acetonitrile is presented. The new method has a much improved chemoselectivity, which is illustrated by a concise total synthesis of the piperidine iminosugar (+)-1,4-dideoxyallonojirimycin.

Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates

Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100°C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.

Synthesis of salicylic acid-based 1,3,4-oxadiazole derivatives coupled with chiral oxazolidinones: Novel hybrid heterocycles as antitumor agents

A series of novel salicylic acid-based 1,3,4-oxadiazoles derivatives coupled with chiral oxazolidinones were synthesized to screen for their in vitro antitumor activity against five human cancer cell lines. Some of these compounds showed good antitumor activities with IC50values ranging from 31.19-57.21 μM. Among the tested compounds 11, 15, 19,23,24, and 34 showed broad-spectrum antitumor activity against all the cell lines. In particular, compound 19 revealed remarkable antitumor activity with IC50 = 31.19-41.87 μM. A431 was the most sensitive cell line against all the compounds studied, followed by HeLa, MCF-7, A549 and HepG2. Structures of newly synthesized compounds were confirmed by IR,1 H NMR, 13C NMR and HRMS spectral data

An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular schmidt/bischler-napieralski/imine-reduction cascade sequence

A novel enantioselective strategy for the total synthesis of (S)-tylophorine was developed in an overall yield of 48% with more than 99% ee from readily avaliable azido acid and phenanthryl alcohol. This route features an Evans stereoselective alkylation and an unprecedented one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence, in which three new bonds and two rings formed in 84% yield. The intramolecular Schmidt rearrangement of the azido aldehyde was proved to be racemization-free.

Dehydrative synthesis of chiral oxazolidinones catalyzed by alkali metal carbonates under low pressure of CO2

Dehydrative synthesis of oxazolidinones from amino alcohols and CO 2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO 2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process.

Synthesis of some 2-Oxazolidinones in mild conditions

One step efficient protocol for the synthesis of 2-oxazolidinones in paste chemical medium is described under microwave activation with 80 % yield.

On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one

The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory {[α]D26 = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory {[α]D26 = - 16.1 (c 5.2, EtOH)}.