(R,R)-DACH-phenyl Trost ligand

Base Information

• Chemical Name: (R,R)-DACH-phenyl Trost ligand
• CAS No.: 138517-61-0
• Molecular Formula: C44H40N2O2P2
• Molecular Weight: 690.761
• European Community (EC) Number: 811-290-0
• UNII: M4RRX95R5F
• DSSTox Substance ID: DTXSID80894121
• Nikkaji Number: J722.188F
• Wikipedia: Trost_ligand
• Mol file: 138517-61-0.mol

Synonyms:138517-61-0;(R,R)-DACH-phenyl Trost ligand;Trost ligand;(R)-Trost ligand;(R,R)-Trost ligand;(R,R)-Dppba;Trost ligand, (R,R)-;M4RRX95R5F;2-diphenylphosphanyl-N-[(1R,2R)-2-[(2-diphenylphosphanylbenzoyl)amino]cyclohexyl]benzamide;Benzamide, N,N'-(1R,2R)-1,2-cyclohexanediylbis[2-(diphenylphosphino)-;(1R,2R)-1,2-Bis((2-(diphenylphosphino)benzoyl)amino)cyclohexane;(1R,2R)-1,2-Bis((2-(diphenylphosphanyl)benzoyl)amino)cyclohexane;(1R,2R)-N,N-Bis(O-(diphenylphosphino)benzoyl)cyclohexane-1,2-diamine;N,N-(1R,2R)-1,2-Cyclohexanediylbis(2-(diphenylphosphino)benzamide);MFCD01631273;(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N'-bis(2'-di-phenylphoshinobenzoyl);(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N-bis(2-diphenylphosphinobenzoyl);Benzamide, N,N-(1R,2R)-1,2-cyclohexanediylbis(2-(diphenylphosphino)-;Benzamide, N,N-1,2-cyclohexanediylbis(2-(diphenylphosphino)-, (1R-trans)-;(1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N/'-BIS(2/'-DIPHENYLPHOSPHINOBENZOYL);(1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2'-DIPHENYLPHOSPHINOBENZOYL);(R,R)-Trost's ligand;UNII-M4RRX95R5F;(1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINOBENZOYL);(R,R)-Dach-phenyltrostligand;SCHEMBL2252584;DTXSID80894121;AKOS015917837;CS-W014410;SC11302;(R,R)-DACH-phenyl Trost ligand, 95%;AS-72512;F31128;J-007150;N,N'-((1R,2R)-cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)benzamide);(1R,2R)-(+)-N,N'-BIS(2-DIPHENYLPHOSPHINOBENZOYL)-1,2-DIAMINOCYCLOHEXANE;(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N'-bis(2'-diphenylphosphinobenzoyl), (R,R)-DACH-Phenyl Trost Ligand;2-(DIPHENYLPHOSPHANYL)-N-[(1R,2R)-2-[2-(DIPHENYLPHOSPHANYL)BENZAMIDO]CYCLOHEXYL]BENZAMIDE

Chemical Property of (R,R)-DACH-phenyl Trost ligand

Chemical Property:

• Melting Point: 134-136 °C
• Boiling Point: 817.038 °C at 760 mmHg
• PKA: 13.35±0.40(Predicted)
• Flash Point: 447.928 °C
• PSA: 85.38000
• LogP: 7.45580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 690.25650252
• Heavy Atom Count: 50
• Complexity: 929

Purity/Quality:

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

(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N'-bis(2'-diphenylphosphinobenzoyl), 98% (R,R)-DACH-Phenyl Trost Ligand ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)NC(=O)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)NC(=O)C5=CC=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)NC(=O)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)NC(=O)C5=CC=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7
• Uses: Trost Ligands for Asymmetric Allylic Alkylation

Technology Process of (R,R)-DACH-phenyl Trost ligand

There total 2 articles about (R,R)-DACH-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: 89.9%

ortho-diphenylphosphinobenzoic acid (17261-28-8) + (1R,2R)-1,2-diaminocyclohexane (20439-47-8) → (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane (138517-61-0,169689-05-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1021/ja00050a013

Reference yield:

ortho-diphenylphosphinobenzoic acid (17261-28-8) + (1R,2R)-cyclohex-4-ene-1,2-diamine (1241684-26-3,208533-40-8) → (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane (138517-61-0,169689-05-8)

Guidance literature:

DOI:10.1016/S0040-4039(97)01417-2

Reference yield: 99.9%

[Pd(allyl)(MeCN)2][OTf] (219983-27-4) + (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane (138517-61-0,169689-05-8) → (R,R)-[(C6H4P(C6H5)2PdC3H5OCNH)2C6H10](OSO2CF3)2

Guidance literature:

In dichloromethane;

DOI:10.1039/a905851f

upstream raw materials:

ortho-diphenylphosphinobenzoic acid

(1R,2R)-1,2-diaminocyclohexane

(1R,2R)-cyclohex-4-ene-1,2-diamine