76588-89-1

Basic information

• Product Name: 2-Oxazolemethanol, 4,5-dihydro-4,4-dimethyl-a-phenyl-
• CAS NO: 76588-89-1
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.257
• Mol File: 76588-89-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Oxazolemethanol, 4,5-dihydro-4,4-dimethyl-a-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolemethanol, 4,5-dihydro-4,4-dimethyl-a-phenyl-(76588-89-1)
• EPA Substance Registry System: 2-Oxazolemethanol, 4,5-dihydro-4,4-dimethyl-a-phenyl-(76588-89-1)

Safety Data

• Hazardous Substances Data: 76588-89-1(Hazardous Substances Data)

Upstream product

• 124-68-5 2-Amino-2-methyl-1-propanol 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 60031-37-0 (4,4-dimethyl-2-oxazolin-2-yl)phenylketone 
• 563-79-1 2,3-Dimethyl-2-butene 

Downstream Products

• 86353-68-6 (3,5-Dichloro-phenyl)-carbamic acid (4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl-methyl ester 

Relevant articles and documents

Synthesis, Reactivity, and Application as Chiral Auxiliaries of the Novel (3R)- and (3S)-4,5-Dihydro-3-hydroxy-4,4,5,5-tetramethyl-3-phenylfuran-2(3H)-ones in the Paterno-Buechi Reaction

Both enantiomers of the novel α-hydroxy-γ-lactone (+/-)-3 (4,5-dihydro-3-hydroxy-4,4,5,5-tetramethyl-3-phenyfuran-2(3H)-one) have been synthesized via hydrolysis of the oxetanes 2 derived from the photochemical cycloaddition of the ketones 1 and 2,3-dimethylbut-2-ene (Paterno-Buechi reaction) involving conventional separation of diastereisomers (Schemes 2 and 3).The absolute configuration of (R)- and (S)-3 and of the corresponding oxetane precursors could be assigned on the basis of an X-ray structural analysis of the (-)-(1S,4R)-camphanoyl derivative (3'S)-5 of (S)-3.O-acylation of (S)- and (+/-)-3 to yield a variety of derivatives ((3'S)- and (3'RS)-5 and (+/-)-7, (+/-)-8, (+/-)-9) was accomplished by deprotonation with BuLi at room temperature and subsequent quenching of the Li alcoholate with acyl chlorides or acid anhydrides, demonstrating the extraordinary chemical stability of 3.Additionally, the course of the temperature-dependent diastereoselective Paterno-Buechi reaction of 2,3-dimethylbut-2-ene to the benzoylformate (S)-7 ( = (S)-1d; obtained from (S)-3) was shown to proceed with 58 percent de at 60 deg C, leading to a decrease of enantiomeric purity in the hydrolysis product 3.

Electron-Transfer Chemistry of the Merostabilized 3,5,5-Trimethyl-2-morpholinon-3-yl Radical

Reductions of 5,6-dihydro-5,5-dimethyl-3-phenyl-1,4-oxazin-2-one (6) to 5,5-dimethyl-3-phenyl-2-morpholinone (8), 2-benzoyl-4,4-dimethyl-2-oxazoline (9) to 2-(hydroxyphenylmethyl)-4,4-dimethyl-2-oxazoline (10), 4-(diphenylmethylene)-2,5-cyclohexadienone (12a) to diphenyl(p-hydroxyphenyl)methane (14a), 4--2,5-cyclohexadienone (12b) to tris(p-hydroxyphenyl)methane (14b), benzil (17) to benzoin, and substituted benzils (17a-c) to substituted benzoins by 3,5,5-trimethyl-2-morpholinon-3-yl radical are described.Intermediate radicals 5,5-dimethyl-3-phenyl-2-morpholinon-3-yl (7), diphenyl(p-hydroxyphenyl)methyl (13a), and tris(p-hydroxyphenyl)methyl (13b) are characterized by EPR spectroscopy.Kinetic analyses of the reductions of 6, 9, 17, and 17a-c are described, and mechanisms and rate laws are shown in Schemes II, III, and VII.Reduction reactions most likely occur by electron transfer.Evidence for electron transfer includes an isotope effect for disproportionation of 1 equal to 1.10 +/- 0.09, correlation of the logarithm of the relative rates of reduction of benzils with ?+ with a ρ of 1.7 +/- 0.1, and observation of electron transfer from 1 to tetracyanoethylene, dianisyloxoammonium perchlorate (21), and paraquat (20).