608130-31-0

Basic information

• Product Name: (R)-2-(N-phenyl-aminooxy)-pent-4-en-1-ol
• Synonyms: (R)-2-(N-phenyl-aminooxy)-pent-4-en-1-ol
• CAS NO: 608130-31-0
• Molecular Weight: 193.246
• Mol File: 608130-31-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (R)-2-(N-phenyl-aminooxy)-pent-4-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(N-phenyl-aminooxy)-pent-4-en-1-ol(608130-31-0)
• EPA Substance Registry System: (R)-2-(N-phenyl-aminooxy)-pent-4-en-1-ol(608130-31-0)

Safety Data

• Hazardous Substances Data: 608130-31-0(Hazardous Substances Data)

Upstream product

• 2100-17-6 4-pentenal 
• 147-85-3 L-proline 
• 586-96-9 Nitrosobenzene 
• 771476-40-5 2-(N-phenyl-aminooxy)-pent-4-enal 

Downstream Products

• 127793-64-0 (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 
• 445289-97-4 (R)-1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl acrylate 
• 548483-77-8 (E)-(R)-7-((4S,6S)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-hepta-1,5-dien-4-ol 

Relevant articles and documents

Prolinate Salts as Catalysts for α-Aminoxylation of Aldehyde and Associated Mechanistic Insights

Potassium and tetrabutylammonium prolinate salts are efficient catalysts in the α-aminoxylation reaction of aldehydes and nitrosobenzene, to afford synthetically useful chiral α-aminoxylated aldehydes in nearly enantiomerically pure form. This is the first reaction in which prolinate is more reactive and enantioselective than proline. Because of its higher reactivity, the catalyst loading can be reduced. A reaction mechanism involving the activation of nitrosobenzene through N-protonation of a hydrogen-bonded water molecule is proposed.

PROCESSES OF ENANTIOSELECTIVELY FORMING AN AMINOXY COMPOUND AND AN 1,2-OXAZINE COMPOUND

Disclosed is a process of enantioselectively forming an aminoxy compound of Formula (3) In formula (3) R1 is one of an aliphatic group and an alicyclic group. R2 is one of hydrogen, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group and an arylalicyclic group. R3 is one of hydrogen, halogen, hydroxyl, and an aliphatic group with a main chain having 1 to about 10 carbon atoms. The respective aliphatic, alicyclic, aromatic, arylaliphatic or arylalicyclic groups of R1, R2, and R3 comprise 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. The process includes contacting a carbonyl compound of Formula (1) and a nitroso compound of Formula (2) in the presence of a chiral catalyst. The chiral catalyst is a compound of Formula (IX)

Use of bifunctional ureas to increase the rate of proline-catalyzed α-aminoxylations

The rate of the proline-catalyzed α-aminoxylation of aldehydes is significantly increased in the presence of a bifunctional urea. Structure-activity relationship data indicate that both an amine and a urea are crucial for rate enhancement. The evidence pr