(R,R)-DACH-naphthyl Trost ligand

Base Information

• Chemical Name: (R,R)-DACH-naphthyl Trost ligand
• CAS No.: 174810-09-4
• Molecular Formula: C52H44 N2 O2 P2
• Molecular Weight: 790.881
• Hs Code.: 2931499090
• European Community (EC) Number: 811-984-3
• DSSTox Substance ID: DTXSID10370165
• Nikkaji Number: J783.104H
• Wikidata: Q72462766
• Mol file: 174810-09-4.mol

Synonyms:174810-09-4;(R,R)-DACH-naphthyl Trost ligand;N,N'-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide);(1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL);2-diphenylphosphanyl-N-[(1R,2R)-2-[(2-diphenylphosphanylnaphthalene-1-carbonyl)amino]cyclohexyl]naphthalene-1-carboxamide;1-Naphthalenecarboxamide, N,N'-(1R,2R)-1,2-cyclohexanediylbis[2-(diphenylphosphino)-;(1R,2R)-(+)-1,2-DIAMINOCYCLOHEXANE-N,N/'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL);MFCD02684551;SCHEMBL2257710;DTXSID10370165;(1R,2R)-(-)-1,2-DiaMinocyclohexane-N,N'-bis(2-diphenylphosphino-1-naphthoyl);N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis-(2-(diphenylphosphino)-1-naphthamide);VXFKMKXTPXVEMU-AWSIMMLFSA-N;AMY11666;ZGA81009;AKOS015911074;CS-W011391;SC11308;1-Naphthalenecarboxamide,N,N'-(1R,2R)-1,2-cyclohexanediylbis[2-(diphenylphosphino)-;AC-26550;AS-74020;(R,R)-DACH-naphthyl Trost ligand, 95%;CS-0213937;A881662;J-011040;(1R)-1beta,2alpha-Bis[2-(diphenylphosphino)-1-naphthylcarbonylamino]cyclohexane;(1R,2R)-1,2-DIAMINOCYCLOHEXANE-N,N'-BIS(2-DIPHENYLPHOSPHINO-1-NAPHTHOYL);N,N'-(1R,2R)-Cyclohexane-1,2-diylbis[2-(diphenylphosphanyl)naphthalene-1-carboxamide];N,N'-(1R,2R)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide];N,N\'-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide);(R,R)-DACH-NAPHTHYL TROST LIGAND;N,N'-((1R,2R)-CYCLOHEXANE-1,2-DIYL)BIS(2-(DIPHENYLPHOSPHINO)-1-NAPHTHAMIDE);ROST LIGAND (NAPHTHYL);2-(DIPHENYLPHOSPHANYL)-N-[(1R,2R)-2-[2-(DIPHENYLPHOSPHANYL)NAPHTHALENE-1-AMIDO]CYCLOHEXYL]NAPHTHALENE-1-CARBOXAMIDE

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

Chemical Property:

• Melting Point: 224-231 °C
• PKA: 13.43±0.40(Predicted)
• PSA: 85.38000
• LogP: 9.76220
• 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:

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

N,N'-(1R,2R)-Cyclohexane-1,2-diylbis[2-(diphenylphosphanyl)naphthalene-1-carboxamide] ^*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=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
• Uses: Trost Ligands for Asymmetric Allylic Alkylation

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

There total 5 articles about (R,R)-DACH-naphthyl 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: 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

Refernces

• 1、 Trost, Barry M.,O'Boyle, Brendan M.. "Synthesis of 7-Epi (+)-FR900482: An epimer of comparable anti-cancer activity". supporting information; experimental part. p. 1369 - 1372. Retrieved 2009/04/10.