376355-58-7

Basic information

• Product Name: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][
• Synonyms: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][;BIPOL-A1(S), (S,S)-N-(5,7-Diox-6-phosphadibenzo[a,c]cyclohepten-6-yl)bis(1-phenylethyl)amine, O,Oμ-(2,2μ-Biphenyldiyl) N,N-bis[(S)-1-phenylethyl]phosphoramidite;N,N-Bis[(1S)-(-)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine;N,N-Bis[(1R)-(+)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine;1,1'-Biphenyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite;N,N-bis[(1R)-1-phenylethyl]-Dibenzo[d,f][1,3,2]dioxaphosphepin-6-aMine;Biphenyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite
• CAS NO: 376355-58-7
• Molecular Formula: C₂₈H₂₆NO₂P
• Molecular Weight: 439.492
• Product Categories: phosphine-amine ligand;Chiral Phosphine;CPN
• Mol File: 376355-58-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 99-102 °C
• Boiling Point: 578.426°C at 760 mmHg
• Flash Point: 303.621°C
• Appearance: white/Powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.31±0.20(Predicted)
• Sensitive: moisture sensitive
• CAS DataBase Reference: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(CAS DataBase Reference)
• NIST Chemistry Reference: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(376355-58-7)
• EPA Substance Registry System: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(376355-58-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 376355-58-7(Hazardous Substances Data)

Usage

Description

N,N-Bis-[(S)-1-PHENYLETHYL]DIBENZO[D F][1,3,2]DIOXAPHOSPHEPIN-6-AMINE is a complex organic compound with a unique structure that features a dibenzo[d,f][1,3,2]dioxaphosphepin core and phenylethyl substituents. This molecule is known for its potential applications in various chemical reactions and processes.

Uses

1. Used in Iridium-Catalyzed Allylic Arylation:
N,N-Bis-[(S)-1-PHENYLETHYL]DIBENZO[D F][1,3,2]DIOXAPHOSPHEPIN-6-AMINE is used as a ligand in the iridium-catalyzed allylic arylation. In this application, the compound plays a crucial role in enhancing the efficiency and selectivity of the reaction, leading to the formation of desired products with improved yields.
2. Used in Copper Complex Preparation for Asymmetric Addition Reactions:
N,N-Bis-[(S)-1-PHENYLETHYL]DIBENZO[D F][1,3,2]DIOXAPHOSPHEPIN-6-AMINE is also utilized in the preparation of a copper complex (Cu2X2L3). This complex is specifically designed to detect transmetalation intermediates in asymmetric addition reactions using ZnEt2. N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F]['s unique structure and properties make it an ideal candidate for this purpose, allowing for better understanding and control of the reaction mechanisms.

Reaction

Ligand for the copper catalyzed, highly regioselective substitution reactions of a wide variety of aromatic substituted allylic halides to form branched chiral products from diverse Grignard reagents. Ligand for the copper catalyzed, highly enantioselective conjugate addition of diethylzinc to eneones and nitro olefins. Ligand for the nickel catalyzed, highly enantioselective hydrovinylation of alkenes. Ligand for the rhodium catalyzed, highly enantioselective hydroformylation of vinylarenes. Ligand for gold catalyzed asymmetric Intramolecular hydroamination of allenes

InChI:InChI=1/C28H26NO2P/c1-21(23-13-5-3-6-14-23)29(22(2)24-15-7-4-8-16-24)32-30-27-19-11-9-17-25(27)26-18-10-12-20-28(26)31-32/h3-22H,1-2H3/t21-,22-/m0/s1

Upstream product

• 1806-29-7 2,2'-dihydroxybiphenyl 
• 21003-56-5 (1S,1'S)-bis(1-phenylethyl)amine 
• 777067-25-1 [(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride 
• 16611-68-0 6-chloro-dibenzo[d,f][1,3,2]-dioxaphosphepin 
• 40648-92-8 hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine 

Relevant articles and documents

On the use of phosphoramidite ligands in copper-catalyzed asymmetric transformations with trialkylaluminum reagents

Phosphoramidites based on BINOL readily react with trimethylaluminum in "noncoordinating" solvents, leading to the corresponding aminophosphine which is the real ligand in copper-catalyzed asymmetric transformations. This artifact explains the experimenta

Efficient, selective, and green: Catalyst tuning for highly enatioselective reactions of ethylene

Fine tuning of the biaryl and amino moieties of Feringa's phosphoramidite ligands yields structurally simpler, yet more efficient and selective, ligands for asymmetric hydrovinylation of vinylarenes and acylic 1,3-dienes. The enantioselectivities and yields observed in the formation of the 3-arylbutenes are among the highest for all asymmetric catalytic processes reported to date for the synthesis of intermediates for the widely used antiinflammatory 2-arylpropionic acids including naproxen, ibuprofen, fenoprofen, and flurbiprofen.

Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: Construction of chiral quaternary centers

Me3Al, Et1Al, and vinylalane species undergo enantioselective conjugate addition to a wide range of 2- or 3-substituted enones (cyclopent-2enones, cyclohex-2-enones, 3-methyl cyclohept-2-enone) in the presence of catalytic amount of copper salt (copper thiophene carboxylate, [Cu(CH3-CN)4]BF4 or [CuOTf]2· C6H6) and tropos-phosphoramidite-based ligand. Thus, chiral quaternary centers can be built, with up to 98% ee after rigorous optimization of experimental conditions. It was shown that the main important parameter was the order of the introduction of the reagents. Then, the generated enantioenriched aluminium enolates and the chiral conjugate adducts were functionalized and used for subsequent reactions.