1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide

Base Information

• Chemical Name: 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide
• CAS No.: 1173895-39-0
• Molecular Formula: C₄₈H₅₂N₂O₈
• Molecular Weight: 784.949
• Mol file: 1173895-39-0.mol

Synonyms:1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide

Chemical Property of 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide

There total 5 articles about 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide 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: 45.0%

2-phenylpropylamine (582-22-9) + 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene-5,5'-dicarboxylic acid (1173894-90-0) → 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-39-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm900472s

Reference yield:

2-phenylpropylamine (582-22-9) + 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-<2,2'-binaphthalene>-5,5'-dicarboxaldehyde (96964-27-1) → 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-39-0)

Guidance literature:

1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-<2,2'-binaphthalene>-5,5'-dicarboxaldehyde; With sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide; In acetonitrile; at 20 ℃;

2-phenylpropylamine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20 ℃;

DOI:10.1021/jm100746q

Reference yield:

(rac)-gossypol (303-45-7) → 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N5,N5'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide (1173895-39-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 3.5 h / 90 °C / Inert atmosphere; Darkness

2.1: potassium carbonate / acetone / 24 h / Inert atmosphere; Reflux

3.1: titanium tetrachloride / 20 °C

3.2: 20 °C

4.1: sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide / acetonitrile / 20 °C

4.2: 20 °C

With sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide; titanium tetrachloride; potassium carbonate; sodium hydroxide; In water; acetone; acetonitrile;

DOI:10.1021/jm100746q

upstream raw materials:

2-phenylpropylamine

1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene-5,5'-dicarboxylic acid

1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-<2,2'-binaphthalene>-5,5'-dicarboxaldehyde

(rac)-gossypol

Downstream raw materials:

1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide

6,6',7,7'-tetrahydroxy-3,3'-dimethyl-1,1',4,4'-tetraoxo-N₅,N₅'-bis(2-phenylpropyl)-1,1',4,4'-tetrahydro-2,2'-binaphthyl-5,5'-dicarboxamide

Refernces

• 1、 Wei, Jun,Kitada, Shinichi,Stebbins, John L.,Placzek, William,Zhai, Dayong,Wu, Bainan,Rega, Michele F.,Zhang, Ziming,Cellitti, Jason,Yang, Li,Dahl, Russell,Reed, John C.,Pellecchia, Maurizio. "Synthesis and biological evaluation of apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins". scheme or table. p. 8000 - 8011. Retrieved 2011/03/19.