N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide

Base Information

• Chemical Name: N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide
• CAS No.: 172138-95-3
• Molecular Formula: C18H20N4O2
• Molecular Weight: 324.382
• European Community (EC) Number: 622-677-7
• DSSTox Substance ID: DTXSID50431401
• Nikkaji Number: J1.218.791B
• Wikidata: Q72462770
• Mol file: 172138-95-3.mol

Synonyms:172138-95-3;N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide;N-[(1S,2S)-2-(pyridine-2-carbonylamino)cyclohexyl]pyridine-2-carboxamide;(+)-N,N/'-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE);(S,S)-DACH-pyridyl Trost ligand;C18H20N4O2;2-Pyridinecarboxamide, N,N'-(1S,2S)-1,2-cyclohexanediylbis-;(1R,2R)-(-)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane;(1S,2S)-1,2-Bis(2-pyridinecarboxamido)cyclohexane;SCHEMBL7218492;DTXSID50431401;BVYFDUZVVBXFBQ-KBPBESRZSA-N;MFCD02684544;AKOS015900176;CS-W011986;(S,S)-DACH-pyridyl Trost ligand, 95%;(S,S)-DACH-pyridyl Trost ligand, 97%;BS-16058;D83188;A907275;(1S,2S)-N,N'-Dipicolinoyl-1,2-diaminocyclohexane;J-013064;N,N'-[(1S,2S)-Cyclohexane-1,2-diyl]di(pyridine-2-carboxamide);(+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide),98%

Chemical Property of N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide

Chemical Property:

• Melting Point: 170 °C
• Boiling Point: 663.366 °C at 760 mmHg
• PKA: 12.51±0.40(Predicted)
• Flash Point: 354.991 °C
• PSA: 83.98000
• Density: 1.255 g/cm³
• LogP: 2.72940
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 324.15862589
• Heavy Atom Count: 24
• Complexity: 403

Purity/Quality:

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

(+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide), min. 98% (S,S)-DACH-Pyridyl Trost Ligand ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)NC(=O)C2=CC=CC=N2)NC(=O)C3=CC=CC=N3
• Isomeric SMILES: C1CC[C@@H]([C@H](C1)NC(=O)C2=CC=CC=N2)NC(=O)C3=CC=CC=N3
• Uses: Trost Ligands for Asymmetric Allylic Alkylation

Technology Process of N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide

There total 5 articles about N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide 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: 86.6%

2-Picolinic acid (98-98-6) + (S,S)-1,2-diaminocyclohexane (21436-03-3) → N,N'-((1S,2S)-cyclohexane-1,2-diyl)dipicolinamide (172138-95-3,218290-24-5)

Guidance literature:

2-Picolinic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 18 - 20 ℃; for 1h;

(S,S)-1,2-diaminocyclohexane; In tetrahydrofuran; at 20 ℃; for 15h; Further stages.;

DOI:10.1002/1615-4169(20010129)343:1<137::AID-ADSC137>3.0.CO;2-V

Reference yield: 80.0%

ethyl-2-picolinate (2524-52-9,1228273-66-2) + (S,S)-1,2-diaminocyclohexane (21436-03-3) → N,N'-((1S,2S)-cyclohexane-1,2-diyl)dipicolinamide (172138-95-3,218290-24-5)

Guidance literature:

With lanthanum(lll) triflate; at 50 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol500593v

Reference yield: 73.0%

carbon monoxide (201230-82-2) + pyridin-2-yl tosylate (57785-86-1) + (S,S)-1,2-diaminocyclohexane (21436-03-3) → N,N'-((1S,2S)-cyclohexane-1,2-diyl)dipicolinamide (172138-95-3,218290-24-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 80 ℃; for 20h; Inert atmosphere; Sealed vial;

DOI:10.1021/ja200818w

upstream raw materials:

2-Picolinic acid

(S,S)-1,2-diaminocyclohexane

benzoic acid

carbon monoxide

Refernces

• 1、 Krska, Shane W.,Hughes, David L.,Reamer, Robert A.,Mathre, David J.,Sun, Yongkui,Trost, Barry M.. "The unusual role of CO transfer in molybdenum-catalyzed asymmetric alkylations". . p. 12656 - 12657. Retrieved 2002.
• 2、 -. "SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS". Page/Page column 75. . Retrieved 2012/06/30.
• 3、 -. "N-cyclopentyl modulators of chemokine receptor activity". . . Retrieved 2008/06/13.