(S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol

Base Information

• Chemical Name: (S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol
• CAS No.: 229184-99-0
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.384
• DSSTox Substance ID: DTXSID20440520
• Nikkaji Number: J945.564G
• Mol file: 229184-99-0.mol

Synonyms:229184-99-0;(S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol;(1S,2S)-1,2-Di(naphthalen-1-yl)ethane-1,2-diol;(1S,2S)-1,2-dinaphthalen-1-ylethane-1,2-diol;SCHEMBL9950211;DTXSID20440520;AKOS015913297;(1S,2S)-1,2-Bis(1-naphthyl)-1,2-ethanediol;J-014901;(S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol, 98%

Chemical Property of (S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 149-151 °C(lit.)
• Refractive Index: 1.732
• Boiling Point: 549.7°Cat760mmHg
• Flash Point: 258.5°C
• PSA: 40.46000
• Density: 1.269g/cm³
• LogP: 4.76000
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 314.130679813
• Heavy Atom Count: 24
• Complexity: 371

Purity/Quality:

97% ^*data from raw suppliers

(S,S)-(?)-1,2-Di(1-naphthyl)-1,2-ethanediol 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2C(C(C3=CC=CC4=CC=CC=C43)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC=C2[C@@H]([C@H](C3=CC=CC4=CC=CC=C43)O)O
• Uses: (S, S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol can be used as: A ligand in the asymmetric sulfoxidation of dihydrothienopyrimidine. A reactant for the preparation of (2S,2′S)-[(1S,2S)-1,2-bis(naphthalen-1-yl)ethane-1,2-diyl] bis[2-(dimethylamino)propanoate], a chiral bisester ligand via condensation reaction with N,N-dimethylamino acid using aldol-Tishchenko condensation catalyst. A reactant to synthesize diol-SnCl4 chiral Bronsted acid complex, which is employed as a catalyst in the allylboration of aldehydes.

Technology Process of (S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol

There total 7 articles about (S,S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol 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:

1-naphthaldehyde (66-77-3) → (R,R)-(+)-1,2-di-naphthalen-1-yl-ethane-1,2-diol (159406-53-8) + meso-1,2-di-naphthalen-1-yl-ethane-1,2-diol + 1,2-di(1-naphthyl)ethane-1,2-diol (229184-99-0)

Guidance literature:

1-naphthaldehyde; With chloro-trimethyl-silane; Ti-(R,R-SALEN); zinc; In acetonitrile; at -10 ℃; for 5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.166667h; Title compound not separated from byproducts;

DOI:10.1021/jo0342875

Reference yield:

2-hydroxy-1,2-di(naphthalen-1-yl)ethyl isobutyrate → (R,R)-(+)-1,2-di-naphthalen-1-yl-ethane-1,2-diol (159406-53-8) + 1,2-di(1-naphthyl)ethane-1,2-diol (229184-99-0)

Guidance literature:

With lithium hydroxide monohydrate; In methanol; at 50 ℃; enantioselective reaction;

DOI:10.1039/d1ob00304f

Reference yield:

1,2-di(naphthalen-1-yl)ethane-1,2-diyl bis(2-methylpropanoate) → (R,R)-(+)-1,2-di-naphthalen-1-yl-ethane-1,2-diol (159406-53-8) + 1,2-di(1-naphthyl)ethane-1,2-diol (229184-99-0)

Guidance literature:

With lithium hydroxide monohydrate; In methanol; at 50 ℃; enantioselective reaction;

DOI:10.1039/d1ob00304f

upstream raw materials:

1-naphthaldehyde

2-Methylpropionic anhydride

(±)-1,2-di(naphthalen-1-yl)ethane-1,2-diol

Refernces

• 1、 Fujii, Kazuki,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji. "Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts". . p. 2778 - 2788. Retrieved 2017/08/23.
• 2、 Li, You-Gui,Tian, Qing-Shan,Zhao, Jun,Feng, Yan,Li, Min-Jie,You, Tian-Pa. "Asymmetric pinacol coupling of aromatic aldehydes catalyzed by a new titanium-Schiff base complex". . p. 1707 - 1710. Retrieved 2007/10/03.