223526-93-0

Basic information

• Product Name: N-(2-hydroxymethylphenyl)-N-(2-propenyl)-4-toluenesulfonylamide
• Synonyms: N-(2-hydroxymethylphenyl)-N-(2-propenyl)-4-toluenesulfonylamide
• CAS NO: 223526-93-0
• Molecular Weight: 317.409
• Mol File: 223526-93-0.mol

Chemical Properties

• CAS DataBase Reference: N-(2-hydroxymethylphenyl)-N-(2-propenyl)-4-toluenesulfonylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxymethylphenyl)-N-(2-propenyl)-4-toluenesulfonylamide(223526-93-0)
• EPA Substance Registry System: N-(2-hydroxymethylphenyl)-N-(2-propenyl)-4-toluenesulfonylamide(223526-93-0)

Safety Data

• Hazardous Substances Data: 223526-93-0(Hazardous Substances Data)

Upstream product

• 223526-92-9 ethyl 2-(2-propenyl-4-toluenesulfonylamino)benzoate 
• 223526-78-1 ethyl 2-(4-methylphenylsulfonamido)benzoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 5344-90-1 2-Aminobenzyl alcohol 
• 90312-02-0 N-(2-hydroxymethylphenyl)-4-methylbenzenesulfonamide 
• 106-95-6 allyl bromide 
• 87-25-2 2-ethoxycarbonylaniline 

Downstream Products

• 223526-79-2 N-(2-formylphenyl)-N-(2-propenyl)-4-toluenesulfonylamide 

Relevant articles and documents

Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels-Alder Reaction

The Pd(II)-catalyzed reaction of N-allyl-2-aminophenols in the presence of PhI(OCOR)2 as the oxidant resulted in an alkoxyacyloxylation process, with the formation of functionalized dihydro-1,4-benzoxazines. The reaction performed in the absence of pallad

Observations concerning the synthesis of heteroatom-containing 9-membered benzo-fused rings by ring-closing metathesis

A set of benzo-fused dienes with a 1,9-relationship and containing a variety of nitrogen and oxygen heteroatoms was readily synthesized. These dienes were then treated with the Grubbs second generation catalyst with the aim of synthesizing the 9-membered benzannelated heterocycles containing two heteroatoms (either O,O, NR,NR or O,NR where R = Ts or Boc). As previously observed in the literature, many of the dienes did not give the expected ring-closed product. However, a number of the desired products did form, namely with the 1,2-dihydrobenzo[c][1,5]oxazonin-7(5H)-one, 5,7-dihydrobenzo[b][1,5]oxazonine-6(2H)-carboxylate and 2,5,6,7-tetrahydrobenzo[b][1,5]oxazonine cores, albeit in poor yields. Rather surprisingly, the N-allyl-N-(2-(N-allyl-4-methylphenylsulfonamido)benzyl)-4-methylbenzenesulfonamide scaffold gave the desired ring-closed 1,6-ditosyl-2,5,6,7-tetrahydro-1H-benzo[b][1,5]diazonine in a high yield. Furthermore, when treated with the catalyst [RuClH(CO)(PPh3)3] the alkene isomerized into conjugation only with the benzylic NTs group and not with the phenyl NTs group to afford the 1,6-ditosyl-2,3,6,7-tetrahydro-1H-benzo[b][1,5]diazonine structure.

Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Br?nsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles

A novel route to 1,3-oxazaheterocycles based on cooperative Ru-H/Br?nsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)3 complex allows for an efficient long distance chain-walking process while the Br?nsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst. (Chemical Equation Presented).

Dienamine and friedel-crafts one-pot synthesis, and antitumor evaluation of diheteroarylalkanals

An asymmetric synthesis of diheteroarylalkanals through one-pot dienamine and Friedel-Crafts reaction is presented. The reaction tolerates a large variety of substituents at different positions of the starting aldehyde and also in the indole nucleophile, and a range of diheterocyclic alkanals can be achieved. Furthermore, we have studied the antiproliferative activity of these new compounds in representative cancer tumor cell lines. All in one: An asymmetric synthesis of diheteroarylalkanals through a one-pot dienamine and Friedel-Crafts reaction is presented (see scheme). The reaction tolerates a large variety of substituents at different positions of the starting aldehyde, and the use of nucleophiles and different diheterocyclic alkanals can also be achieved. The antiproliferative activity of these new compounds in different cancer tumor cell lines has also been investigated and it was found that, with the appropriate substitution, the compounds are as cytotoxic as Cisplatin.

Cyanative alkene-aldehyde coupling: Ni(0)-NHC-Et2AlCN mediated chromanol synthesis with high cis-selectivity at room temperature

Described are several classes of Ni(0) mediated cyanative alkene-aldehyde coupling reactions, providing 6-membered cores, which complement existing cyclization technology in several respects. Et2AlCN was used as both a cyclization accelerator and CN source. The NHC ligand may have a positive effect in differentiating reductive elimination and syn-β-hydride elimination.

An intramolecular azomethine ylide-alkene cycloaddition approach to pyrrolo[3,2-c]quinolines-synthesis of a C2-truncated martinelline model

The hexahydropyrrolo[3,2-c]quinoline core found in the Martinella alkaloids was constructed through an intramolecular [3+2] azomethine ylide-alkene cycloaddition. Some chemical manipulations of the tricycle are reported.

An approach to the pyrroloquinoline core of martinelline and martinellic acid

An expedient method for the assembly of the pyrroloquinoline skeleton found in the martinelline alkaloids using a [3+2] cycloaddition of an azomethine ylide and an alkene has been developed.