N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)

Base Information

• Chemical Name: N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)
• CAS No.: 205495-66-5
• Molecular Formula: C₅₂H₄₄N₂O₂P₂
• Molecular Weight: 790.881
• DSSTox Substance ID: DTXSID60472002
• Nikkaji Number: J750.454C
• Wikidata: Q72445439
• Mol file: 205495-66-5.mol

Synonyms:205495-66-5;N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide);(S,S)-DACH-naphthyl Trost Ligand;(1S,2S)-(-)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL);1-Naphthalenecarboxamide, N,N'-(1S,2S)-1,2-cyclohexanediylbis[2-(diphenylphosphino)-;2-diphenylphosphanyl-N-[(1S,2S)-2-[(2-diphenylphosphanylnaphthalene-1-carbonyl)amino]cyclohexyl]naphthalene-1-carboxamide;(1S,2S)-1,2-Bis[[[2-(diphenylphosphino)naphthalen-1-yl]carbonyl]amino]cyclohexane;VXFKMKXTPXVEMU-ZYBCLOSLSA-N;MFCD02684552;SCHEMBL2249426;DTXSID60472002;N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis-(2-(diphenylphosphino)-1-naphthamide);AMY11667;AKOS016842797;CS-W009567;(1S,2S)-(-)-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPTHOYL)-1,2-DIAMINOCYCLOHEXANE;(S,S)-DACH-naphthyl Trost Ligand, 95%;A879567;J-013405;N,N'-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide];N,N'-[(1S,2S)-Cyclohexane-1,2-diyl]bis[2-(diphenylphosphanyl)naphthalene-1-carboxamide];2-(DIPHENYLPHOSPHANYL)-N-[(1S,2S)-2-[2-(DIPHENYLPHOSPHANYL)NAPHTHALENE-1-AMIDO]CYCLOHEXYL]NAPHTHALENE-1-CARBOXAMIDE

Chemical Property of N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)

Chemical Property:

• Melting Point: 232-237 °C
• PKA: 13.43±0.40(Predicted)
• PSA: 85.38000
• LogP: 9.76220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 11.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 790.28780265
• Heavy Atom Count: 58
• Complexity: 1170

Purity/Quality:

99%, ^*data from raw suppliers

(1S,2S)-1,2-Bis[[[2-(diphenylphosphino)naphthalen-1-yl]carbonyl]amino]cyclohexane ^*data from reagent suppliers

Safty Information:

• 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=C(C=CC3=CC=CC=C32)P(C4=CC=CC=C4)C5=CC=CC=C5)NC(=O)C6=C(C=CC7=CC=CC=C76)P(C8=CC=CC=C8)C9=CC=CC=C9
• Isomeric SMILES: C1CC[C@@H]([C@H](C1)NC(=O)C2=C(C=CC3=CC=CC=C32)P(C4=CC=CC=C4)C5=CC=CC=C5)NC(=O)C6=C(C=CC7=CC=CC=C76)P(C8=CC=CC=C8)C9=CC=CC=C9

Technology Process of N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)

There total 5 articles about N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) 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: 55.0%

(1R,2R)-1,2-diaminocyclohexane (20439-47-8) + 2-diphenylphosphino-1-naphthanoic acid (178176-80-2) → (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) (174810-09-4,205495-66-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃; for 17h; Inert atmosphere;

DOI:10.1021/ol800127a

Reference yield:

1,2-diaminocyclohexane-N,N'-bis(2'-diphenylphosphonium-1-naphthoyl) (205495-66-5) → (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) (174810-09-4,205495-66-5)

Guidance literature:

With XDA ultra-highly cross-linked macroporous resin; In hexane; at 30 - 80 ℃; for 4h; Temperature;

Reference yield:

methyl 2-hydroxy-1-naphthoate (947-65-9) → (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) (174810-09-4,205495-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / pyridine / CH₂Cl₂ / 14 h / 0 °C

2.1: 95 percent / bis(benzonitrile)palladium dichloride / toluene / 26 h / Heating

3.1: 88 percent / barium hydroxide octahydrate / methanol / 25 h / Heating

4.1: Et₃N; diphenylchlorophosphite / CH₂Cl₂ / 5 h / 0 - 20 °C

4.2: 51 percent / DMAP / CH₂Cl₂ / 12 h / 25 °C

With pyridine; bis(benzonitrile)palladium(II) dichloride; barium hydroxide octahydrate; Diphenyl phosphorochloridite; triethylamine; In methanol; dichloromethane; toluene; 1.1: triflation / 2.1: Substitution / 3.1: Hydrolysis / 4.1: phosphorylation / 4.2: amidation;

DOI:10.1021/ja000547d

upstream raw materials:

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

2-diphenylphosphino-1-naphthanoic acid

methyl 2-hydroxy-1-naphthoate

2-diphenylphosphino-1-naphthoic acid methyl ester

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