(S,S)-ANDEN-Phenyl Trost Ligand

Base Information

• Chemical Name: (S,S)-ANDEN-Phenyl Trost Ligand
• CAS No.: 138517-65-4
• Molecular Formula: C54H42N2O2P2
• Molecular Weight: 812.887
• DSSTox Substance ID: DTXSID90451542
• Nikkaji Number: J1.825.539A,J750.455A
• Wikidata: Q82271612
• Mol file: 138517-65-4.mol

Synonyms:(S,S)-ANDEN-Phenyl Trost Ligand;138517-65-4;Benzamide, N,N'-(11S,12S)-(9,10-dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)-;N,N'-(11S,12S)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide];2-diphenylphosphanyl-N-[(15S,16S)-16-[(2-diphenylphosphanylbenzoyl)amino]-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl]benzamide;(S,S)-ANDEN-Phenyl Trost Ligand,(+)-(11S,12S)Bis[2'-(diphenylphosphino)benzamido]-9,10-dihydro-9,10-;DTXSID90451542;AKOS040768754;CS-0201428;E75172;J-007151;(11S,12S)-11,12-Bis[2-(diphenylphosphino)benzoylamino]-9,10-ethano-9,10-dihydroanthracene;2-diphenylphosphanyl-N-[(15S,16S)-16-[(2-diphenylphosphanylbenzoyl)amino]-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9(14),10,12-hexaenyl]benzamide;N,N'-[[(11S,12S)-9,10-Dihydro-9alpha,10alpha-ethanoanthracene]-11,12-diyl]bis[2-(diphenylphosphino)benzamide]

Chemical Property of (S,S)-ANDEN-Phenyl Trost Ligand

Chemical Property:

• Melting Point: 66-67 °C
• PKA: 12.75±0.40(Predicted)
• PSA: 92.36000
• LogP: 9.54060
• XLogP3: 10.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 812.27215258
• Heavy Atom Count: 60
• Complexity: 1240

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S,S)-ANDEN-PHENYL TROST LIGAND 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3C(=O)NC4C(C5C6=CC=CC=C6C4C7=CC=CC=C57)NC(=O)C8=CC=CC=C8P(C9=CC=CC=C9)C1=CC=CC=C1
• Isomeric SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3C(=O)N[C@@H]4[C@H](C5C6=CC=CC=C6C4C7=CC=CC=C57)NC(=O)C8=CC=CC=C8P(C9=CC=CC=C9)C1=CC=CC=C1
• Uses: Asymmetric allylic alkylation ligand.

Technology Process of (S,S)-ANDEN-Phenyl Trost Ligand

There total 2 articles about (S,S)-ANDEN-Phenyl Trost Ligand which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.8%

ortho-diphenylphosphinobenzoic acid (17261-28-8) + (9R,10R,11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine (138517-66-5) → (+)-11(S),12(S)-bis-<2'-(diphenylphosphino)benzamido>-9,10-dihydro9,10-ethanoanthracene (138517-65-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/ja00050a013

Reference yield:

9,10-dihydro-11(S),12(S)-diisocyanato-9,10-ethanoanthracene → (+)-11(S),12(S)-bis-<2'-(diphenylphosphino)benzamido>-9,10-dihydro9,10-ethanoanthracene (138517-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.5 aq. NaOH / 2 h

2: 98.8 percent / DCC, DMAP / CH₂Cl₂ / 10 h / Ambient temperature

With dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/ja00050a013

upstream raw materials:

ortho-diphenylphosphinobenzoic acid

(9R,10R,11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine