benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate

Base Information

• Chemical Name: benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate
• CAS No.: 146965-86-8
• Molecular Formula: C₃₇H₃₈O₄
• Molecular Weight: 546.706
• Mol file: 146965-86-8.mol

Synonyms:benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate

Chemical Property of benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate

There total 10 articles about benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate 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: 74.0%

benzyl 6-<3-(1-adamantyl)-4-(2-propenyl)phenyl>-2-naphthoate (146966-07-6) → benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate (146965-86-8)

Guidance literature:

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; In water; for 6h; Heating;

DOI:10.1021/jm00026a006

Reference yield:

4-bromo-phenol (106-41-2) → benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate (146965-86-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / conc. H₂SO₄ / CH₂Cl₂ / 8 h / Ambient temperature

2: 86 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / dimethylformamide / 4 h / Ambient temperature

3: 1.) Mg, I₂, 2.) ZnCl₂, 3.) NiCl₂*1,2-bis(diphenylphosphino)ethane

4: 99 percent / 1.1 M tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature

5: 79 percent / 2 N NaOH / methanol / 8 h / Heating

6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h

7: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / -70 °C

8: 97 percent / LiCl, (PPh₃)2PdCl₂ / dimethylformamide / 0.67 h / 100 °C

9: 74 percent / trimethylamine N-oxide dihydrate, pyridine, OsO₄ / H₂O / 6 h / Heating

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; osmium(VIII) oxide; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; trimethylamine-N-oxide; sulfuric acid; tetrabutyl ammonium fluoride; iodine; sodium hydride; magnesium; triethylamine; lithium chloride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00026a006

Reference yield:

1-adamanthanol (768-95-6) → benzyl 6-<3-(1-adamantyl)-4-(2,3-dihydroxypropyl)phenyl>-2-naphthoate (146965-86-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / conc. H₂SO₄ / CH₂Cl₂ / 8 h / Ambient temperature

2: 86 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / dimethylformamide / 4 h / Ambient temperature

3: 1.) Mg, I₂, 2.) ZnCl₂, 3.) NiCl₂*1,2-bis(diphenylphosphino)ethane

4: 99 percent / 1.1 M tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature

5: 79 percent / 2 N NaOH / methanol / 8 h / Heating

6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h

7: 89 percent / pyridine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / -70 °C

8: 97 percent / LiCl, (PPh₃)2PdCl₂ / dimethylformamide / 0.67 h / 100 °C

9: 74 percent / trimethylamine N-oxide dihydrate, pyridine, OsO₄ / H₂O / 6 h / Heating

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; osmium(VIII) oxide; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; trimethylamine-N-oxide; sulfuric acid; tetrabutyl ammonium fluoride; iodine; sodium hydride; magnesium; triethylamine; lithium chloride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00026a006

upstream raw materials:

benzyl 6-<3-(1-adamantyl)-4-(2-propenyl)phenyl>-2-naphthoate

4-bromo-phenol

1-adamanthanol

2-(1-adamantyl)-4-bromophenol

Refernces

• 1、 Charpentier,Bernardon,Eustache,Millois,Martin,Michel,Shroot. "Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes". . p. 4993 - 5006. Retrieved 2007/10/03.