888329-88-2

Basic information

• Product Name: 3-(2-phenylethynyl)oxazolidin-2-one
• Synonyms: 3-(2-phenylethynyl)oxazolidin-2-one
• CAS NO: 888329-88-2
• Molecular Weight: 187.198
• Mol File: 888329-88-2.mol
• Article Data: 58

Chemical Properties

• CAS DataBase Reference: 3-(2-phenylethynyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-phenylethynyl)oxazolidin-2-one(888329-88-2)
• EPA Substance Registry System: 3-(2-phenylethynyl)oxazolidin-2-one(888329-88-2)

Safety Data

• Hazardous Substances Data: 888329-88-2(Hazardous Substances Data)

Usage

Description

3-(2-phenylethynyl)oxazolidin-2-one is a nitrogen-substituted alkyne that is highly reactive and strongly polarized. It serves as a versatile building block in organic synthesis and has been utilized in the design of numerous chemical transformations.

Uses

Used in Organic Synthesis:
3-(2-phenylethynyl)oxazolidin-2-one is used as a building block for the synthesis of various organic compounds due to its high reactivity and strong polarization.
Used in Asymmetric Synthesis:
3-(2-phenylethynyl)oxazolidin-2-one is used as a useful reagent in asymmetric synthesis, enabling the selective formation of enantiomerically pure compounds.
Used in the Preparation of Highly Reactive Keteniminium Ions:
3-(2-phenylethynyl)oxazolidin-2-one serves as a precursor for the generation of highly reactive keteniminium ions, which are valuable intermediates in organic chemistry for the synthesis of a wide range of target molecules.

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 536-74-3 phenylacetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 71-43-2 benzene 
• 1483-82-5 phenylethynyl chloride 
• 58723-96-9 (Z)-1,2-dichloro-2-phenylethylene 
• 100-52-7 benzaldehyde 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 1258403-15-4 1-((Z)-2-bromo-1-iodovinyl)benzene 
• 7436-90-0 2,2-dibromostyrene 
• 637-44-5 phenylpropyolic acid 
• 768-60-5 4-methoxyphenylacetylen 

Downstream Products

• 1085526-73-3 3,3'-(2-phenylethene-1,1-diyl)dioxazolidin-2-one 
• 1134172-72-7 3-[(Z)-1-(4-nitrophenyl)-2-phenylbut-1-enyl]oxazolidin-2-one 
• 1134172-74-9 methyl (2E,4Z)-4-(2-oxooxazolidin-3-yl)-5-phenylhepta-2,4-dienoate 
• 1134172-63-6 3-[(Z)-2-phenylbuta-1,3-dienyl]oxazolidin-2-one 
• 478918-54-6 3-[(1Z)-2-phenylprop-1-en-1-yl]-1,3-oxazolidin-2-one 
• 1134172-46-5 3-[(1Z)-2-phenylbut-1-en-1-yl]-1,3-oxazolidin-2-one 
• 1134172-70-5 3-[(Z)-1-benzoyl-2-phenylbut-1-enyl]oxazolidin-2-one 
• 1268824-73-2 1-(2-oxooxazolidin-3-yl)-2-phenylethane-1,2-dione 
• 1356545-28-2 1-(2-oxo-oxazolidin-3-yl)-2-phenylpentane-1,3-dione 
• 1356545-12-4 (E)-1-(2-oxo-1,3-oxazolidin-3-yl)-2-phenylethenyl 2-{[(tertbutoxy)carbonyl]amino}-3-methylbutanoate 
• 1356545-17-9 (E)-3-phenylacrylic acid (E)-1-(2-oxo-oxazolidin-3-yl)-2-phenylvinyl ester 
• 1356545-09-9 propionic acid (E)-1-(2-oxo-oxazolidin-3-yl)-2-phenylvinyl ester 
• 1356545-14-6 3,5-dimethoxybenzoic acid (E)-1-(2-oxo-oxazolidin-3-yl)-2-phenylvinyl ester 
• 1356545-11-3 isobutyric acid (E)-1-(2-oxo-oxazolidin-3-yl)-2-phenylvinyl ester 

Relevant articles and documents

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Synthesis of dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline through Cu(OTf)2-catalyzed reactions of N-acyliminium ions with ynamides

An efficient approach to access functionalized dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline skeletons has been developed through the addition-cyclization process of ynamides 8 with N-acyliminium ions generated from N,O-acetals 6,7. The reactions were conducted under the catalysis of Cu(OTf)2, and a number of functionalized dihydro-[1,3]oxazino[4,3-a] isoindoles 9a-9y and tetrahydroisoquinolines 10a-10g, 11a-11p were generated in 48–98% yields. When chiral ynamides 8n-8u were used, optically pure products 11a-11p could be obtained with good to excellent yields and diastereoselectivities.

One-pot synthesis of alkynylthiocyanates by phase-transfer reagent

Thiocyano-group widely exist in natural products and drug structures. A novel one-pot synthesis of alkynylthiocyanates from terminal alkynes, [hydroxy(tosyloxy)iodo]benzene and potassium thiocyanate by phase-transfer reagent involving the hypervalent iodine intermediates in transition metal-free conditions was developed. The internal alkynylthiocyanates could be used to synthesize some important compounds such as 5-thiocyanato-1,2,3-triazoles and (Z)-α-thiocyanato-vinyl trifluoromethanesulfonate.