17559-27-2

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 300-57-2 allylbenzene 
• 160879-62-9 methyl 1-phenylprop-2-enyl carbonate 

Downstream Products

• 133609-18-4 O-cinnamylhydroxylamine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 162365-58-4 N-benzyl-N-(1-phenyl-2-propenyl)hydroxylamine 
• 161330-98-9 (E)-N-benzyl-O-(3-phenylallyl)hydroxylamine 

Relevant academic research and scientific papers

Organocatalytic Radical Involved Oxidative Cross-Coupling of N-Hydroxyphthalimide with Benzylic and Allylic Hydrocarbons

The cross-coupling reaction between N-hydroxyphthalimide and various benzylic and allylic hydrocarbons was realized through an organocatalytic radical-mediated process involving C(sp3)-O bond formation using tert-butyl hydroperoxide (t-BuOOH) as an oxidant and tetra-n-butylammonium iodide [(n-Bu]4NI] as a catalyst, during which the phthalimide N-oxyl (PINO) radical and benzylic and allylic radicals were generated in situ and underwent the selective radical/radical cross-coupling reaction. This novel method provides a convenient metal-free approach to the synthesis of O-alkylated hydroxy imides under mild reaction conditions.

Cu-facilitated C-O bond formation using N-hydroxyphthalimide: Efficient and selective functionalization of benzyl and allylic C-H bonds

A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and PhI(OAc)2 in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals. Copyright

Hydroxylamines as oxygen atom nucleophiles in transition-metal-catalyzed allylic substitution

(Chemical Equation Presented) The viability of hydroxylamines as nucleophiles in transition-metal-catalyzed allylic substitutions was examined. We have found that the oxygen atom of hydroxylamines having an N-electron-withdrawing substituent (also known a

Probing the 'active site' of diamine oxidase: Structure-activity relations for histamine potentiation by O-alkylhydroxylamines on colonic epithelium

The responses of the canine colonic epithelium to histamine are potentiated by O-alkylhydroxylamines. A study of a series of such compounds suggested that active compounds had the structure R-O-NH2, substitution of a nitrogen led to total loss of activity. The locus of the potentiation effect was traced to the inhibition of diamine oxidase. A new series of aliphatic and aromatic O-alkylhydroxylamines were synthesized to explore further the structure-activity relations of this effect. The potentiating effects of these compounds were determined by examining the changes in short circuit current (I(sc)) produced by histamine and from the activity of a soluble preparation of diamine oxidase. We found that 1) branched compounds are less active than their straight chain counterparts, 2) greater steric bulk of the aliphatic substituent decreased activity, 3) the presence of a double bond had no significant effect though a triple bond reduced activity, 4) longer straight chain compounds were less active than the shorter chain derivatives and 5) all benzylic compounds were less active than the straight chain aliphatics. O-1-benzyl was inactive however the meta or para oxygen substituted compounds as well as the O-(1-E-Cinnamyl) derivative were active. A current model for the action of diamine oxidase proposes a crucial role for a trihydroxyphenylalanine quinone cofactor as part of the active site together with a copper atom. Using molecular modeling based on our inhibition data we are able to define the region of space that is just beyond the reactive carbonyl of the trihydroxyphenylalanine residue at the active site of diamine oxidase. We suggest that a negatively charged species, such as an aspartate or a glutamate, resides in a trough about 7 to 8 A from the trihydroxyphenylalanine carbonyl carbon and this species aids in the strong selective binding of substrates such as putrescine and histamine.

Facile generation of alkoxy radicals from N-alkoxyphthalimides

N-Alkoxyphthalimides, stable and readily accessible from alcohols and alkyl halides, are found to be very efficient alkoxy radical precursors.