151309-96-5

Basic information

• Product Name: 10-Undecenoic acid, 4-nitrophenyl ester
• CAS NO: 151309-96-5
• Molecular Formula: C17H23NO4
• Molecular Weight: 305.374
• Mol File: 151309-96-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 10-Undecenoic acid, 4-nitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Undecenoic acid, 4-nitrophenyl ester(151309-96-5)
• EPA Substance Registry System: 10-Undecenoic acid, 4-nitrophenyl ester(151309-96-5)

Safety Data

• Hazardous Substances Data: 151309-96-5(Hazardous Substances Data)

Upstream product

• 112-38-9 10-undecenoic acid 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 100-02-7 4-nitro-phenol 
• 38460-95-6 undec-10-enoyl chloride 

Downstream Products

• 1647-16-1 1,10-decadiene 
• 19398-85-7 trans,trans-2,8-decadiene 
• 55682-65-0 dipropyl-1,3-butadiene 
• 957372-89-3 C₃₁H₅₁NO₅ 
• 957372-81-5 C₃₅H₅₉NO₄ 

Relevant articles and documents

Olefins from biomass feedstocks: Catalytic ester decarbonylation and tandem Heck-type coupling

With the goal of avoiding the need for anhydride additives, the catalytic decarbonylation of p-nitrophenylesters of aliphatic carboxylic acids to their corresponding olefins, including commodity monomers like styrene and acrylates, has been developed. The reaction is catalyzed by palladium complexes in the absence of added ligands and is promoted by alkali/alkaline-earth metal halides. Combination of catalytic decarbonylation and Heck-type coupling with aryl esters in a single pot process demonstrates the viability of employing a carboxylic acid as a "masked olefin" in synthetic processes. This journal is

Selective Decarbonylation of Fatty Acid Esters to Linear α-Olefins

Selective decarbonylation of p-nitrophenol esters of fatty acids to the corresponding linear α-olefins (LAOs) was achieved using palladium catalysis. After extensive ligand screening, a mixed-ligand system exploiting the trans-spanning diphosphine XantPhos and an N-heterocyclic carbene (IPr) was identified as the most effective in yielding high α-selectivity and high conversions of the ester (>98% selectivity, >90% conversion using 2.5 mol % of PdCl2 and 5 mol % of the ligands, 190 °C, 2-2.5 h). On the basis of insights from modeling at the density functional level of theory, we propose that the mixed-ligand set achieves high α-selectivity by promoting olefin dissociation from the palladium center following β-hydride elimination, which is especially facilitated both by the combined steric bias of the mixed-ligand set and by the ability of the XantPhos ligand to coordinate in both mono- and bidentate fashions.

C-GLYCOLIPIDS WITH ENHANCED TH-1 PROFILE

The invention is directed to novel synthetic C-glycolipids that selectively induce a ThI -type immune response characterized by enhanced IL- 12 secretion and increased activation of dendritic cells. The compounds of the invention are thereby useful in treating infections, cancers, cell proliferative disorders, and autoimmune diseases, both directly and as adjuvants.