19312-06-2

Usage

Uses

Used in Chemical Synthesis:
4,4-Dimethyl-2-phenyl-2-oxazoline is used as a ligand in the Suzuki coupling reaction for the formation of ester-ammonium salts via the rupture of the oxazoline ring. This application is significant in the synthesis of various organic compounds and materials.
Used in Coordination Chemistry:
In coordination chemistry, 4,4-Dimethyl-2-phenyl-2-oxazoline is used to form complexes with zinc halides, such as [ZnX2(ox)2] (ox = 4,4-Dimethyl-2-phenyl-2-oxazoline), where X = Cl, Br, or I. These complexes are of interest in studying the coordination properties and potential applications of zinc halide complexes.

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2032, 1960 DOI: 10.1021/ja01493a045Tetrahedron Letters, 27, p. 5269, 1986 DOI: 10.1016/S0040-4039(00)85187-4

InChI:InChI=1/C11H13NO/c1-11(2)8-13-10(12-11)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3

Upstream product

• 19312-05-1 N-(2-hydroxyl-1,1-dimethylethyl) benzamide 
• 40186-36-5 N-(chloro-tert-butyl)-benzamide 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 65-85-0 benzoic acid 
• 53244-68-1 2-(methylthio)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 109-72-8 n-butyllithium 
• 80762-49-8 2-(m-chlorophenyl)-4,4-dimethyl-4,5-dihydrooxazole 
• 30093-99-3 4,4-dimethyl-2-oxazoline 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 118559-32-3 4,4-dimethyl-2-(tri-n-butylstannyl)-2-oxazoline 
• 129665-83-4 Li(4,4-dimethyl-2-oxazolinyl) 
• 598-30-1 sec.-butyllithium 

Downstream Products

• 42449-39-8 8,8-dichloro-5-dichloromethylene-3,3-dimethyl-8a-phenyl-tetrahydro-oxazolo[3,2-c][1,3]oxazin-7-one 
• 13758-35-5 3,4,4-trimethyl-2-phenyl-4,5-dihydro-oxazolium; iodide 
• 56446-24-3 N-tert-butyl-2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-benzamide 
• 709-25-1 N-(2-methylallyl)benzamide 
• 83656-90-0 1-Benzo[b]thiophen-2-yl-1-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-ethanol 
• 107400-32-8 methyl 2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzoate 
• 130131-76-9 Bis-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-methanone 
• 129819-16-5 2-n-butyl-4,4-dimethyl-2-phenyloxazolidine 
• 1009-14-9 phenyl butyl ketone 
• 92592-46-6 2-[3,3-Diphenyl-3H-isobenzofuran-(1E)-ylideneamino]-2-methyl-propan-1-ol 
• 57629-47-7 2-(2-Butylphenyl)-4,4-dimethyl-2-oxazoline 
• 87643-00-3 4-dibenzothienyl-2-(4,4-dimethyl-2-oxazolin-2-yl)phenylmethanol 
• 133341-93-2 4,4-dimethyl-2-[2-(prop-2-enyl)]phenyl-2-oxazoline 
• 75704-08-4 1-difluoromethyl-1-trifluoromethyl-2-benzofuran-3(1H)-one 

Relevant academic research and scientific papers

Arylation of Heterocycles via Rhodium-Catalyzed C-H Bond Functionalization

(Equation presented) A new method for the rhodium-catalyzed arylation of a variety of heterocycles has been developed. The reaction provided moderate to good yields of the arylated products. A preliminary mechanistic investigation of this reaction revealed the intermediacy of an isolable N-heterocyclic carbene complex.

Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates

A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.

Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

Insights into the antiproliferative mechanism of (C^N)-chelated half-sandwich iridium complexes

Transition metal-based anticancer compounds, as an alternative to platinum derivatives, are raising scientific interest as they may present distinct although poorly understood mechanisms of action. We used a structure-activity relationship-based methodology to investigate the chemical and biological features of a series of ten (C^N)-chelated half-sandwich iridiumIII complexes of the general formula [IrCp?(phox)Cl], where (phox) is a 2-phenyloxazoline ligand forming a 5-membered metallacycle. This series of compounds undergoes a fast exchange of their chlorido ligand once solubilised in DMSO. They were cytotoxic to HeLa cells with IC50 values in the micromolar range and induced a rapid activation of caspase-3, an apoptosis marker. In vitro, the oxidative power of all the complexes towards NADH was highlighted but only the complexes bearing substituents on the oxazoline ring were able to produce H2O2 at the micromolar range. However, we demonstrated using a powerful HyPer protein redox sensor-based flow cytometry assay that most complexes rapidly raised intracellular levels of H2O2. Hence, this study shows that oxidative stress can partly explain the cytotoxicity of these complexes on the HeLa cell line and gives a first entry to their mechanism of action. This journal is

Nickel-catalyzed reductive defunctionalization of esters in the absence of an external reductant: Activation of C-O bonds

The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C-O bond in O-Alkyl esters is reported. Various groups, such as N-containing heterocycles, esters, amides, and even arene rings can function as a directing group.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates: Facile synthesis of 1,2-amino alcohols

A new radical-mediated intramolecular β-C(sp3)-H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alcohol starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcohols. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)-H functionalization of alcohols. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative.

Catalytic Alkene Difunctionalization via Imidate Radicals

The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands

C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides