146896-52-8

Basic information

• Product Name: 2-phenyl-5-methylene-4,5-dihydrooxazole
• Synonyms: 2-phenyl-5-methylene-4,5-dihydrooxazole
• CAS NO: 146896-52-8
• Molecular Weight: 159.188
• Mol File: 146896-52-8.mol
• Article Data: 79

Chemical Properties

• CAS DataBase Reference: 2-phenyl-5-methylene-4,5-dihydrooxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-5-methylene-4,5-dihydrooxazole(146896-52-8)
• EPA Substance Registry System: 2-phenyl-5-methylene-4,5-dihydrooxazole(146896-52-8)

Safety Data

• Hazardous Substances Data: 146896-52-8(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 2450-71-7 Propargylamine 
• 65-85-0 benzoic acid 
• 1464-98-8 N-(prop-2-yn-1-yl)benzamide 
• 455-14-1 4-trifluoromethylphenylamine 
• 7648-30-8 ethyl 2,2-difluoro-2-iodoacetate 
• 1373942-84-7 tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate 
• 5221-67-0 5-methyl-2-phenyloxazole 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 123883-85-2 2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrooxazole 

Downstream Products

• 5221-67-0 5-methyl-2-phenyloxazole 
• 1214922-06-1 5-(iodomethyl)-2-phenyloxazole 
• 80281-50-1 5-(bromomethyl)-2-phenyloxazole 
• 1391708-74-9 5-(hydroperoxymethyl)-2-phenyloxazole 
• 238433-75-5 2-phenyl-5-(hydroxymethyl)oxazole 
• 1616777-92-4 2-hydroxy-1-(3-nitrophenyl)-3-(2-phenyloxazol-5-yl)propan-1-one 
• 1616777-93-5 2-hydroxy-1-(4-nitrophenyl)-3-(2-phenyloxazol-5-yl)propan-1-one 
• 1616777-94-6 2-hydroxy-3-(2-phenyloxazol-5-yl)-1-(4-(trifluoromethyl)phenyl)propan-1-one 
• 1616777-95-7 4-(2-hydroxy-3-(2-phenyloxazol-5-yl)propanoyl)benzonitrile 
• 1616777-96-8 2-hydroxy-1-(naphthalen-1-yl)-3-(2-phenyloxazol-5-yl)propan-1-one 
• 1616777-97-9 2-hydroxy-1-(naphthalen-2-yl)-3-(2-phenyloxazol-5-yl)propan-1-one 
• 1616777-98-0 2-hydroxy-3-(2-phenyloxazol-5-yl)-1-(thiophen-2-yl)propan-1-one 
• 1616777-99-1 1-cyclohexyl-2-hydroxy-3-(2-phenyloxazol-5-yl)propan-1-one 
• 1616778-00-7 3-hydroxy-4-(2-phenyloxazol-5-yl)butan-2-one 

Relevant articles and documents

Synthesis of Oxazoles by Tandem Cycloisomerization/Allylic Alkylation of Propargyl Amides with Allylic Alcohols: Zn(OTf)2 as π Acid and σ Acid Catalyst

A Zn(OTf)2-catalyzed tandem cycloisomerization/allylic alkylation of N-(propargyl)arylamides and allylic alcohols to produce oxazole derivatives has been successfully developed. The zinc catalyst served as π acid and also σ acid in this reaction. The target allylic oxazoles have been transformed into multisubstituted diene structures, which are potential aggregation-induced emission active optical materials.

The core of the matter-arene substitution determines the coordination and catalytic behaviour of tris(1-phosphanyl-1′-ferrocenylene)arene gold(i) complexes

Changing the aromatic core of C3-symmetric tris(ferrocenyl)arene-based tris-phosphanes has profound effects on their coordination behaviour towards gold(i). Depending on the arene (s-triazine, benzene, or trifluorobenzene), four different coordination modes can be distinguished and their preference has been rationalised using computational methods. The corresponding 1 : 1 ligand-to-metal complexes, studied by variable-temperature NMR spectroscopy, revealed fluctional behaviour in solution. Given the presence of up to three or six ferrocenylene spacers per complex, their electrochemistry was investigated. The redox-responsive nature of the complexes can be advantageously exploited in the catalytic ring-closing isomerisation of N-(2-propyn-1-yl)benzamide, where the benzene-based 2 : 3 ligand-to-metal complex has been shown to display multiple activity states depending on the degree of (reversible) oxidation in a preliminary trial.

Gold-Catalyzed One-Pot Synthesis of Polyfluoroalkylated Oxazoles from N-Propargylamides Under Visible-Light Irradiation

A gold-catalyzed synthesis of polyfluoroalkylated oxazoles from N-propargylamides under visible-light irradiation has been developed. These reactions display excellent compatibility of radicals and gold catalysts under visible-light irradiation. Mechanistic experiments indicate that polyfluoroalkyl iodides play a dual role in enhanced compatibility of radicals and gold catalysts through assisted protodeauration of vinyl gold and reactivated the gold catalyst. In addition, PPh3AuNTf2 not only activates N-propargylamide to generate vinyl gold intermediate, but also greatly promotes homolysis of polyfluoroalkyl iodides under blue light irradiation.

T-Shaped Gold→Stiborane Complexes as Carbophilic Catalysts: Influence of the Peripheral Substituents

As part of our efforts toward the discovery of new late transition metal catalysts, we synthesized [(o-(Ph2P)C6H4)2(o-C6Cl4O2)SbPh)Au]+ (3+) and [(o-(iPrsu

Novel zwitterionic complexes arising from the coordination of an ambiphilic phosphorus-aluminum ligand to gold

Coordination of Mes2PC(CHPh)AltBu2 to metal chlorides has been studied. Bridging P→M-Cl→Al coordinations were observed with Rh and Pd fragments, while chloride abstraction systematically occurred with gold. The resulting zwitterionic

Catalytic ring-closing reactions of gold compounds containing bis(phosphino)ferrocene ligands

The efficiency of various gold compounds containing bis(phosphino)ferrocene ligands for catalyzing ring-closing reactions was examined. Six commercially available bis(phosphino)ferrocene ligands: 1,1′-bis(ditert-butylphosphino)ferrocene (dtbpf), 1,1′-bis(

Synthesis and Properties of Hydrazino Amino Acyclic Carbenes of Gold(I), Platinum(II), Palladium(II) and Rhodium(III)

The nucleophilic addition of protected and substituted hydrazine derivatives to isonitrile complexes of gold(I), platinum(II), palladium(II) and rhodium(III) provides the corresponding hydrazino amino acyclic carbene complexes. These are characterized by

Metal Confinement through N-(9-Alkyl)fluorenyl-Substituted N-Heterocyclic Carbenes and Its Consequences in Gold-Catalysed Reactions Involving Enynes

A series of gold(I) and gold(III) complexes containing bulky bis-N,N′-(9-alkylfluorenyl) heterocyclic carbene (RF-NHC) ligands have been prepared in high yields from appropriate imidazolinium, imidazolium and benzimidazolium salts. In all complexes, the carbene ligand provides high steric protection of the Au?X bond trans to the carbenic C atom. Irrespective of the metal oxidation state, the complexes showed high efficiency in a tandem 3,3-rearrangement/Nazarov reaction of an enynyl acetate. One of the AuIII complexes, [AuCl3(RF-NHC)], was further found to be suitable for the efficient cyclisation of a propargylcarboxamide. Furthermore, unlike related NHC–gold(I) complexes based on conventional bulky N-heterocyclic carbenes (notably, 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr), 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) and 1,3-(bis-tert-butyl)imidazol-2-ylidene (ItBu)), the studied [AuICl(RF-NHC)] complexes catalysed the conversion of a 1,6-enyne in the presence of indole into a single product; this arises from the embracing character of the ligand, which prevents indole addition on one of the catalytic intermediates. A structure/selectivity relationship was established for all carbenes tested that took into account percent buried volumes and topographic steric maps. The results illustrate the high potential of confining NHCs in organic synthesis.

Triple the fun: Tris(ferrocenyl)arene-based gold(i) complexes for redox-switchable catalysis

The modular syntheses of C3-symmetric tris(ferrocenyl)arene-based tris-phosphanes and their homotrinuclear gold(i) complexes are reported. Choosing the arene core allows fine-tuning of the exact oxidation potentials and thus tailoring of the electrochemical response. The tris[chloridogold(i)] complexes were investigated in the catalytic ring-closing isomerisation of N-(2-propyn-1-yl)benzamide, showing cooperative behaviour vs. a mononuclear chloridogold(i) complex. Adding one, two, or three equivalents of 1,1'-diacetylferrocenium[tetrakis(perfluoro-tert-butoxy)aluminate] as an oxidant during the catalytic reaction (in situ) resulted in a distinct, stepwise influence on the resulting catalytic rates. Isolation of the oxidised species is possible, and using them as (pre-)catalysts (ex situ oxidation) confirmed the activity trend. Proving the intactness of the P-Au-Cl motif during oxidation, the tri-oxidised benzene-based complex has been structurally characterised. This journal is

Bicyclic (amino)(borata)carbene derived from diazadiborinine and isonitrile

The reaction of 1,4,2,5-diazadiborinine (1) with two equivalents of an aryl isonitrile afforded a bicyclic product containing an indole unit (2) or ketenimine moiety (3), suggesting the generation of a B,N-carbene intermediate formed via a [4+2] cycloaddi

The Power of Ferrocene, Mesoionic Carbenes, and Gold: Redox-Switchable Catalysis

Catalysis with gold(I) complexes is a useful route for synthesizing a variety of important heterocycles. Often, silver(I) additives are necessary to increase the Lewis acidity at the gold(I) center and to make them catalytically active. We present here a

Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis

Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).

Asymmetric Allylation by Chiral Organocatalyst-Promoted Formal Hetero-Ene Reactions of Alkylgold Intermediates

An unprecedented catalytic asymmetric allylation of isatins and isatin-derived ketimines is reported enabled by a gold and chiral organocatalyst cooperative catalysis strategy. This method offers expeditious access to chiral 2,5-disubsituted alkylideneoxazolines containing vicinal stereogenic centers, mainly in optically pure form, and which are otherwise impossible to access. Mechanistic evidence reveals the presence of an alkylgold intermediate, and an X-ray crystal structure of the allylgold species illuminates its unique stability and reactivity. An asymmetric formal hetero-ene reaction of this gold intermediate, involving a dearomatization process, is enabled with assistance of a quinine-derived squaramide catalyst. This novel discovery extends the synthetic applications of gold complexes and the versatility of gold catalysis.