254990-11-9

Basic information

• Product Name: C₁₉H₂₁N
• Synonyms: C₁₉H₂₁N
• CAS NO: 254990-11-9
• Molecular Weight: 263.382
• Mol File: 254990-11-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: C₁₉H₂₁N(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₉H₂₁N(254990-11-9)
• EPA Substance Registry System: C₁₉H₂₁N(254990-11-9)

Safety Data

• Hazardous Substances Data: 254990-11-9(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 87751-69-7 rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene 
• 73930-97-9 3-acetoxy-1,3-diphenylpropene 

Relevant articles and documents

First chiral [2.2]paracyclophane-derived phosphite ligands: Synthesis and application in asymmetric reactions

First representatives of chiral phosphite ligands derived from 4,5-dihydroxy[2.2]paracyclophane have been synthesized. A possibility of the use of these compounds in the reactions of asymmetric Pd- and Ir-catalyzed allylic amination of 1,3-diphenylprop-2-enyl acetate with pyrrolidine and Rh-catalyzed hydrogenation of dimethyl itaconate has been demonstrated.

An improved class of phosphite-oxazoline ligands for Pd-catalyzed allylic substitution reactions

A method for generation of Pd/phosphite-oxazoline catalysts containing an alkyl backbone chain has been successfully applied to Pd-catalyzed allylic substitution reactions. By carefully selecting the substituents at both the alkyl backbone chain and the oxazoline of the ligand, as well as the configuration of the biaryl phosphite group, high activities (TOF > 8000 mol substrate × (mol Pd × h)?1) and excellent enantioselectivities (ee's up to 99%) have been achieved for many hindered and unhindered substrates with a wide range of C-, O-, and N-nucleophiles (73 substitution products in total). Moreover, DFT and NMR studies of the key Pd-allyl complexes allowed us to better understand the origin of the excellent enantioselectivities observed experimentally. The useful application of the Pd/phosphite-oxazoline catalysts was demonstrated by the syntheses of many chiral carbobicycles, with multiples stereocenters, by simple sequential reactions involving Pd-allylic substitution and either 1,6-enyne cyclization or Pauson?Khand enyne cyclization.

Aminoalkyl-phosphine (P,N) ligands with pentane-2,4-diyl backbone in asymmetric allylic substitution reactions

Abstract: The asymmetric allylic substitution reaction of rac-1,3-diaryl-2-propenyl acetates with several C- and N-nucleophiles catalyzed by the palladium-complexes of eleven structurally analogous aminoalkyl-phosphines (P,N) with pentane-2,4-diyl backbone is reported. The role of the N-substituents and the influence of the ligand/palladium molar ratio on the activity and enantioselectivity of the catalytic system are studied. The solvent and the temperature dependence of the catalytic reaction were also assessed yielding enantioselectivities up to 95% in alkylation and 90% in amination processes under optimized reaction conditions.