86217-38-1

Usage

Chemical Properties

mp 130-132°C

InChI:InChI=1/C9H9NO2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m1/s1

Upstream product

• 124143-63-1 3-hydroxy-2-phenyl-propionic acid hydrazide 
• 79624-36-5 3-nitroso-4-phenyl-2-oxazolidinone 
• 14441-94-2 4-methoxy-1,3-oxazolidin-2-one 
• 591-51-5 phenyllithium 
• 80639-71-0 2-phenylethyl azidocarbonate 
• 124-38-9 carbon dioxide 
• 20989-17-7 Phenylglycinol 
• 144-55-8 sodium hydrogencarbonate 
• 105-58-8 Diethyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124718-93-0 2-azido-2-phenylethanol 
• 97678-52-9 (2-hydroxy-1-phenylethyl)urea 
• 25070-24-0 α-hydroxyacetophenone oxime 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 79624-36-5 3-nitroso-4-phenyl-2-oxazolidinone 
• 20989-17-7 Phenylglycinol 
• 86217-50-7 N-<(R)-1-(1-Naphthyl)ethyl>-(4S)-phenyl-2-oxazolidone-3-carboxamide 
• 86217-51-8 N-<(R)-1-(1-Naphthyl)ethyl>-(4R)-phenyl-2-oxazolidone-3-carboxamide 
• 142673-43-6 (S)-3-((1S,2R,4R)-2-Methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-4-phenyl-oxazolidin-2-one 
• 142673-33-4 (R)-3-((1S,2R,4R)-2-Methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-4-phenyl-oxazolidin-2-one 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 199387-45-6 4-phenyl-3-((E)-3-phenylacryloyl)oxazolidin-2-one 
• 17539-82-1 3-butyl-4-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions

Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: Theoretical evidence for an asynchronous concerted pathway

The one-pot reaction of chlorosulfonyl isocyanate (CSI) with epoxides having phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained in ratios close to 1:1 in the cyclization reactions. The best yields of these compounds were obtained in dichloromethane (DCM). Together with 16 known compounds, two novel oxazolidinone derivatives and two novel cyclic carbonates were synthesized with an efficient and straightforward method. Compared to the existing methods, the synthetic approach presented here provides the following distinct advantageous: being a one-pot reaction with metal-free reagent, having shorter reaction times, good yields and a very simple purification method. Moreover, using the density functional theory (DFT) method at the M06-2X/6-31+G(d,p) level of theory the mechanism of the cycloaddition reactions has been elucidated. The further investigation of the potential energy surfaces associated with two possible channels leading to oxazolidinones and five-membered cyclic carbonates disclosed that the cycloaddition reaction proceeds via an asynchronous concerted mechanism in gas phase and in DCM.

Synthesis of Chiral 5-Aryl-2-oxazolidinones via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Ring-Opening of Styrene Oxides

An efficient biocatalytic approach for enantio- and regioselective ring-opening of styrene oxides with cyanate was developed by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, generating the corresponding chiral 5-aryl-2-oxazoli

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

Cycloaddition of Aziridine with CO2/CS2 Catalyzed by Amidato Divalent Lanthanide Complexes

This is the first time that the amidato lanthanide amides ({LnLn[N(SiMe3)2]THF}2 (n = 1, Ln = Eu (1); n = 2, Ln = Eu (3), Yb (4); HL1 = tBuC6H4CONHC6H3(iPr)2; HL2 = C6H5CONHC6H3(iPr)2) and {L3Eu[N(SiMe3)2]THF}{L32Eu(THF)2} (2) (HL3 = ClC6H4CONHC6H3(iPr)2)) were applied in the cycloaddition reactions of aziridines with carbon dioxide (CO2) or carbon disulfide (CS2) under mild conditions. The corresponding oxazolidinones and thiazolidine-2-thiones were obtained in good to excellent yields with good functional group tolerance.

Synthesis method and application of chiral 2-carbonyl oxazoline

The invention discloses a synthesis method of a chiral compound with a structural formula. According to the synthesis method, 50 mol% zinc chloride is used as a catalyst, 20.0 mmol of dicyandiamide and 10.5335 g of D-phenylglycinol are added, 50 mL of chlorobenzene is taken as a solvent, after a reflux reaction is carried out for 3 days, column chromatography isolation is conducted, petroleum ether/dichloromethane (1/9) is utilized for elution, collected second component points are naturally volatilized, and then monocrystal(R)-4-phenyloxazoline-2-ketone is obtained. According to application of the chiral compound crystal (I), a good catalysis effect is shown in a Henry reaction of ethyl pyruvate and nitromethane, and the conversion rate of the ethyl pyruvate and nitromethane reaches 95%.

Regioselective Ring-Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4-Aryloxazolidinones

A biocatalytic approach towards a range of 4-aryloxazolidinones is developed using a halohydrin dehalogenase from Ilumatobacter coccineus (HheG) as biocatalyst. The method is based on the HheG-catalyzed α-position regioselective ring-opening of styrene oxide derivatives with cyanate as a nucleophile, producing the corresponding 4-aryloxazolidinones in moderate to good yields. Synthesis of enantiopure 4-aryloxazolidinones is also achievable using chiral epoxide materials. (Figure presented.).

Method of biocatalytically synthesizing 4-substituted oxazolidinone compound

The invention discloses a biocatalytic technology of synthesizing a 4-substituted oxazolidinone compound by carrying out a reaction on a halohydrin dehalogenase catalyzed epoxy compound and cyanate. The reaction takes the epoxy compound as a primer, cyanate as a nucleophilic ring opening reagent and halohydrin dehalogenase which is originated from an Ilumatobacter coccineus strain and has high alpha-offensive ring opening area selectivity as a biocatalyst. The reaction is carried out in a water phase and is mild in reaction condition. The invention is the biocatalytic method of catalyzing theepoxy compound to synthesize the 4-substituted oxazolidinone compound by using the halohydrin dehalogenase for the first time. The method has a wide application prospect in design of an oxazolidinonedrug and green manufacturing aspect thereof.

Oxazoline metal compound, preparation method thereof and application of oxazoline metal compound as catalyst

The invention provides an oxazoline metal compound which has a structure shown as a formula (I), wherein n is 2 or 3, R1 is -OCH3 or -N(CH3)2, R2 is one of an alkyl group and a phenyl group, and M isMg or Zn. The oxazoline metal compound provided by the invention has high-activity silazane-based metal center; compared with a catalyst with a zinc alkyl or aluminum alkyl center in the prior art, the oxazoline metal compound provided by the invention has very high activity when catalyzing lactide or caprolactone to perform ring-opening polymerization, can realize monomer polymerization at room temperature, has equivalent selectivity to racemic lactide and improves the regularity of the microscopic chain structure of a polymerization product. Shown by experimental results, for polylactic acidprepared with the method, the conversion rate can reach 98 percent, the stereoscopic regularity (Pm) of the obtained polylactic acid can reach 0.53, and the conversion rate of polycaprolactone can reach 99 percent.

Synthesis of oxazolidinones: Rhodium-catalyzed C-H amination of: N -mesyloxycarbamates

N-Mesyloxycarbamates undergo intramolecular C-H amination reactions to afford oxazolidinones in good to excellent yields in the presence of rhodium(ii) carboxylate catalysts. The reaction is performed under green conditions and potassium carbonate is used, forming biodegradable potassium mesylate as a reaction by-product. This method enables the production of electron-rich, electron-deficient, aromatic and heteroaromatic oxazolidinones in good to excellent yields. Conformationally restricted cyclic secondary N-mesyloxycarbamates furnish cis-oxazolidinones in high yields and selectivity; DFT calculations are provided to account for the observed selectivity. trans-Oxazolidinones were prepared from acyclic secondary N-mesyloxycarbamates using Rh2(oct)4. The selectivity was reverted with a cytoxazone N-mesyloxycarbamate precursor using large chiral rhodium(ii) carboxylate complexes, affording the corresponding cis-oxazolidinone. This orthogonal selectivity was used to achieve the formal synthesis of (-)-cytoxazone.