501919-45-5

Basic information

• Product Name: 2-Nonanone, 4-phenyl-, (4S)-
• CAS NO: 501919-45-5
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• Mol File: 501919-45-5.mol
• Article Data: 44

Chemical Properties

• CAS DataBase Reference: 2-Nonanone, 4-phenyl-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nonanone, 4-phenyl-, (4S)-(501919-45-5)
• EPA Substance Registry System: 2-Nonanone, 4-phenyl-, (4S)-(501919-45-5)

Safety Data

• Hazardous Substances Data: 501919-45-5(Hazardous Substances Data)

Upstream product

• 14309-57-0 Non-3-en-2-on 
• 98-80-6 phenylboronic acid 
• 18402-83-0 (E)-non-3-en-2-one 
• 603-33-8 triphenylbismuthane 
• 3262-89-3 triphenylboroxine 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 

Downstream Products

• 1370330-68-9 C₁₆H₂₆O 

Relevant articles and documents

Heterogeneous Chiral Diene-Rh Complexes for Asymmetric Arylation of α,β-Unsaturated Carbonyl Compounds, Nitroalkenes, and Imines

A chiral diene ligand with tertiary alkyl amine-derived secondary amide moiety was immobilized on cross-linked polystyrene (PS) by radical polymerization, which was combined with Rh to form heterogeneous chiral Rh complexes (PS-diene Rh?Cl). PS-diene Rh?Cl catalyzed asymmetric arylation reactions of α,β-unsaturated carbonyl compounds (ketones, esters, and amides), nitroalkenes, and imines afforded the desired products in high yields with excellent enantioselectivities. PS-diene Rh?Cl is stable in air, can be stored for several months, and can be reused more than 10 times without any reduction of either yield or enantioselectivity. We also developed a method of activation of PS-diene Rh?Cl to generate more active species. (Figure presented.).

A diastereomeric pair of sulfoxide-containing chiral MOP-type ligands: Preparation and application to rhodium-catalyzed asymmetric 1,4-addition reactions

(R,SS)-Sulfoxide-MOP (L2) and (R,RS)-sulfoxide-MOP (L3) were developed as a diastereomeric pair of sulfoxide-containing chiral MOP-type ligands. These two ligands also represent the first monosulfoxide analogues of BINAP. The chiral ligand L2 was successfully applied to the highly enantioselective rhodium-catalyzed 1,4-addition between α,β-unsaturated ketones or esters and arylboronic acids, and exhibited a broad substrate scope when the reaction was performed using 1.5 mol% Rh in cyclohexane/H2O (10:1) at 40 °C under mild basic conditions.

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.