58635-82-8

Basic information

• Product Name: (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline
• Synonyms: (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline
• CAS NO: 58635-82-8
• Molecular Weight: 281.354
• Mol File: 58635-82-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline(58635-82-8)
• EPA Substance Registry System: (S,S)-2-benzyl-4-methoxymethyl-5-phenyl-2-oxazoline(58635-82-8)

Safety Data

• Hazardous Substances Data: 58635-82-8(Hazardous Substances Data)

Upstream product

• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 52075-14-6 (4S,5S)-(-)-4,5-dihydro-4-methoxymethyl-2-methyl-5-phenyloxazole 
• 53732-41-5 (4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole 
• 51594-34-4 (1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol 
• 5442-34-2 ethyl 2-phenylacetimidate hydrochloride 

Downstream Products

• 63007-17-0 (S)-1-((4S)-4r-methoxymethyl-5t-phenyl-4,5-dihydro-oxazol-2-yl)-1-phenyl-ethanol 
• 63007-16-9 (R)-1-((4S)-4r-methoxymethyl-5t-phenyl-4,5-dihydro-oxazol-2-yl)-1-phenyl-ethanol 
• 73697-99-1 ((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-(4-methoxy-phenyl)-phenyl-methanol 
• 73698-03-0 ((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl-thiophen-2-yl-methanol 
• 73697-97-9 ((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl-p-tolyl-methanol 
• 73697-95-7 1-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-3-methyl-1-phenyl-butan-1-ol 
• 73697-92-4 1-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-1-phenyl-butan-1-ol 
• 73697-94-6 1-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1-phenyl-propan-1-ol 
• 69766-02-5 1-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-1-phenyl-propan-1-ol 
• 63007-16-9 1-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-1-phenyl-ethanol 
• 115156-63-3 (R)-Hydroxy-naphthalen-1-yl-phenyl-acetic acid 
• 73698-08-5 (S)-Hydroxy-naphthalen-1-yl-phenyl-acetic acid 
• 64471-38-1 (S)-Hydroxy-phenyl-thiophen-2-yl-acetic acid 
• 320348-18-3 (+)-hydroxy(phenyl)2-thienylacetic acid 

Relevant articles and documents

Effect of chain length on radical to carbanion cyclo-coupling of bromoaryl alkyl-linked oxazolines: 1,3-Areneotropic migration of oxazolines

(Chemical Equation Presented) 2-Halophenylalkyl-2-oxazolines with alkyl chain spacers of two to six C atoms (n = 0-4) were prepared and their S RN1-type reactions with several base systems examined. The best conditions to promote cyclocoupling to the corresponding benzocycloalkane derivatives involved use of LDA in THF. The precursors with 3-C-atom and 4-C-atom spacers gave good yields of 2-(1′-phenylindan-1′-yl)-2- oxazolines and 2-(1-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)-2-oxazoline, respectively. The major products from the precursor with a 5-C-atom spacer were derivatives of benzocycloheptane in which the oxazoline group had undergone a novel areneotropic migration from the end of the spacer to the benzo ring. The product from reaction of the corresponding 2-C-atom precursor was a 9-oxazolinophenanthrene derivative. EPR spectroscopy showed the intermediates of the LDA-promoted reactions to be radical anions of the product benzocycloalkanes. This supported an SRN1-type chain mechanism involving initial production of aryl radicals connected to azaenolate ions via the spacer groups. Intramolecular radical to carbanion coupling then generated ring-closed benzocycloalkane radical anions that transferred an electron to more precursor. Diastereoselective radical to carbanion cyclo-coupling reactions were carried out with 2-bromophenylpropyl precursors containing chiral 2-oxazolines. The diastereoselectivity achievable was modest, but the product diastereoisomeric Indane derivatives were easily separable by chromatography.