4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide

Base Information

• Chemical Name: 4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide
• CAS No.: 121758-19-8
• Molecular Formula: C28H28 N2 O4 S2
• Molecular Weight: 520.673
• Hs Code.: 29215990
• European Community (EC) Number: 826-673-8
• DSSTox Substance ID: DTXSID50370008
• Nikkaji Number: J773.370D
• Wikidata: Q76146071
• Mol file: 121758-19-8.mol

Synonyms:121758-19-8;(1R,2R)-N,N'-di-p-Toluenesulfonyl-1,2-diphenyl-1,2-ethylenediamine;N,N'-((1R,2R)-1,2-Diphenylethane-1,2-diyl)bis(4-methylbenzenesulfonamide);(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine;4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide;(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine, min. 98%;SCHEMBL2068549;(1R,2R)-N,N'-Ditosyl-1,2-diphenyl-1,2-ethanediamine;DTXSID50370008;WEA75819;MFCD00269673;(1R,2R)-(+)-N,N'-Di-p-toluenesulfonyl-1,2-diphenyl-1,2-ethylenediamine;BS-14995;CS-0093700;I11867;(1R,2R)-N,N'-Ditosyl-1,2-diphenylethylenediamine;J-004631;(1R,2R)-N,N/'-Ditosyl-1,2-diphenylethylenediamine;(1R,2R)-(+)-N,N'-Di-p-Tosyl-1,2-diphenyl-ethylenediamine;N,N'-[(1R,2R)-1,2-Diphenylethane-1,2-diyl]bis(4-methylbenzene-1-sulfonamide)

Chemical Property of 4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide

Chemical Property:

• Melting Point: 203-208 °C
• Refractive Index: 1.6510 (estimate)
• Boiling Point: 697.1oC at 760 mmHg
• Flash Point: 375.4oC
• PSA: 109.10000
• Density: 1.1673 (rough estimate)
• LogP: 7.98620
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 520.14904973
• Heavy Atom Count: 36
• Complexity: 794

Purity/Quality:

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

(1R,2R)-N,N'-Di-p-tosyl-1,2-diphenyl-1,2-ethylenediamine, min. 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(C2=CC=CC=C2)C(C3=CC=CC=C3)NS(=O)(=O)C4=CC=C(C=C4)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@H](C2=CC=CC=C2)[C@@H](C3=CC=CC=C3)NS(=O)(=O)C4=CC=C(C=C4)C

Technology Process of 4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide

There total 2 articles about 4-methyl-N-[(1R,2R)-2-[(4-methylphenyl)sulfonylamino]-1,2-diphenylethyl]benzenesulfonamide 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: 89.0%

(R,R)-1,2-diphenylethylenediamine (35132-20-8) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-((1R,2R)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethyl)benzenesulfonamide (121758-19-8)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1039/b716938h

Reference yield:

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-((1R,2R)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethyl)benzenesulfonamide (121758-19-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/adsc.201200338

Reference yield: 94.0%

4-methyl-N-((1R,2R)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethyl)benzenesulfonamide (121758-19-8) + tert-butyl prop-2-yn-1-yl carbonate (790300-19-5) → (2R,3R)-5-methylene-2,3-diphenyl-1,4-ditosylpiperazine

Guidance literature:

4-methyl-N-((1R,2R)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethyl)benzenesulfonamide; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bis[2-(diphenylphosphino)phenyl] ether; In dichloromethane; for 0.0333333h; Inert atmosphere; Sealed tube; Sonication;

tert-butyl prop-2-yn-1-yl carbonate; In dichloromethane; at 23 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03708

upstream raw materials:

(R,R)-1,2-diphenylethylenediamine

p-toluenesulfonyl chloride

(S,S)-1,2-diphenyl-1,2-diaminoethane

Downstream raw materials:

(S)-nona-1,2-dien-4-ol

(4R,5R)-2-bromo-1,3-bis[(4-methylphenyl)sulfonyl]-4,5-diphenyl-1,3,2-diazaborolidine

(R)-N₁-(1-methyl-2-oxo-2-phenylethyl)-4-methyl-1-benzenesulfonamide

Refernces

• 1、 Kucherenko, Alexander S.,Siyutkin, Dmitry E.,Nigmatov, Albert G.,Chizhov, Alexander O.,Zlotin, Sergei G.. "Chiral primary amine tagged to ionic group as reusable organocatalyst for asymmetric Michael reactions of C-nucleophiles with α,β-unsaturated ketones". supporting information. p. 3078 - 3086. Retrieved 2013/01/15.
• 2、 Hilgraf, Robert,Pfaltz, Andreas. "Chiral bis(N-sulfonylamino)phosphine- and TADDOL-phosphite-oxazoline ligands: Synthesis and application in asymmetric catalysis". . p. 61 - 77. Retrieved 2007/10/03.