1245819-01-5

Basic information

• Product Name: (R)-1-methoxy-4-(2-nitro-1-phenylethyl)benzene
• Synonyms: (R)-1-methoxy-4-(2-nitro-1-phenylethyl)benzene
• CAS NO: 1245819-01-5
• Molecular Weight: 257.289
• Mol File: 1245819-01-5.mol

Chemical Properties

• CAS DataBase Reference: (R)-1-methoxy-4-(2-nitro-1-phenylethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-methoxy-4-(2-nitro-1-phenylethyl)benzene(1245819-01-5)
• EPA Substance Registry System: (R)-1-methoxy-4-(2-nitro-1-phenylethyl)benzene(1245819-01-5)

Safety Data

• Hazardous Substances Data: 1245819-01-5(Hazardous Substances Data)

Upstream product

• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 98-80-6 phenylboronic acid 
• 102-96-5 (2-nitroethenyl)benzene 
• 5720-07-0 4-methoxyphenylboronic acid 

Relevant articles and documents

Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance

Multifunctional isoquinoline-oxazolines (MIQOXs) were conceived and synthesized from commercially available chiral amino acids. The multifunctional role of MIQOXs was demonstrated by Pd-catalyzed highly enantioselective addition of arylboronic acids to nitrostyrenes, and by the discovery of novel antifungal candidates.

Palladium-catalyzed asymmetric addition of arylboronic acids to nitrostyrenes

A palladium-catalyzed asymmetric addition of arylboronic acids to nitrostyrene is reported. The catalytic system employing iPr-IsoQuinox as a chiral ligand in MeOH solvent under an air atmosphere provides the chiral diarylsubstituted products in high yields with good enantioselectivities. A variety of functionalized nitrostyrenes can be used, and the method tolerates some variation in arylboronic acid scope. The stereochemical outcome can be explained using a stereochemical model.

Aqueous Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Chiral Diene Rhodium Complex under Batch and Continuous-Flow Conditions

A rhodium-chiral diene complex immobilized on amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin (PS-PEG-diene?-Rh) has been developed. The immobilized rhodium-chiral diene complex (PS-PEG-diene?-Rh) efficiently catalyzed the asymmetric 1,4-addition of various arylboronic acids to cyclic or linear enones in water under batch conditions to give the corresponding β-arylated carbonyl compounds in excellent yields and with excellent enantioselectivity. The catalyst was readily recovered by simple filtration and reused 10 times without loss of its catalytic activity and enantioselectivity. Moreover, a continuous-flow asymmetric 1,4-addition in a flow reactor containing PS-PEG-diene?-Rh proceeded efficiently at 50 °C with retention of high enantioselectivity. Long-term continuous-flow asymmetric 1,4-addition during 12 h readily gave the desired product on a 10 g scale with high enantioselectivity.

Rhodium-catalyzed Asymmetric Arylation of Nitroalkenes Powered by Simple Chiral Sulfur-Olefin Ligands

An efficient rhodium-catalyzed enantioselective addition of potassium organotrifluoroborates to nitroalkenes powered by simple chiral sulfur-olefin ligands is reported. This protocol is applicable to a broad range of 2-aryl-, alkyl-, and heteroaryl-substituted nitroalkenes, allowing access to diverse chiral β,β-disubstituted nitroethanes in good to excellent yields with high enantioselectivity under mild conditions.

Rhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids with nitroalkenes: Reaction mechanism and development of homogeneous and heterogeneous catalysts

Asymmetric 1,4-addition reactions with nitroalkenes are valuable because the resulting chiral nitro compounds can be converted into various useful species often used as chiral building blocks in drug and natural product synthesis. In the present work, asymmetric 1,4-addition reactions of arylboronic acids with nitroalkenes catalyzed by a rhodium complex with a chiral diene bearing a tertiary butyl amide moiety were developed. Just 0.1 mol% of the chiral rhodium complex could catalyze the reactions and give the desired products in high yields with excellent enantioselectivities. The homogeneous catalyst thus developed could be converted to a reusable heterogeneous metal nanoparticle system using the same chiral ligand as a modifier, which was immobilized using a polystyrene-derived polymer with cross-linking moieties, maintaining the same level of enantioselectivity. To our knowledge, this is the first example of asymmetric 1,4-addition reactions of arylboronic acids with nitroalkenes in a heterogeneous system. Wide substrate generality and high catalytic turnover were achieved in the presence of sufficient water without any additives such as KOH or KHF2 in both homogeneous and heterogeneous systems. Various insights relating to a rate-limiting step in the catalytic cycle, the importance of water, role of the secondary amide moiety in the ligand, and active species in the heterogeneous system were obtained through mechanistic studies.

Rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to nitroalkenes using olefin-sulfoxide ligands

An efficient rhodium/olefin-sulfoxide catalyzed asymmetric conjugate addition of organoboronic acids to a variety of nitroalkenes has been developed, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be highly effective and a

Rhodium-catalyzed highly enantioselective addition of arylboronic acids to 2-nitrostyrenes by tert-butanesulfinylphosphine ligand

Particularly picky ligands! An efficient (S/C, substrate/catalyst, up to 500) Rh-catalyzed enantioselective addition of arylboronic acids to 2-nitrostyrenes under mild conditions was developed, which gave excellent yields (up to 99 %) and enantioselectivi

Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes using chiral bicyclo [3.3.0] diene ligands

(Figure Presented) Old before l diene: An efficient rhodium/ diene-catalyzed asymmetric conjugate addition of organoboronic acids to challenging nitroalkene substrates that lack α substituents has been developed. Chiral bicyclo[3.3.0] dienes were found to