Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate

Base Information

• Chemical Name: Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate
• CAS No.: 106685-41-0
• Molecular Formula: C29H30O3
• Molecular Weight: 426.555
• Hs Code.: 2918992090
• European Community (EC) Number: 808-698-6
• UNII: W05XV3TPP3
• DSSTox Substance ID: DTXSID00441277
• Nikkaji Number: J3.522.343F
• Wikidata: Q72488319
• Mol file: 106685-41-0.mol

Synonyms:106685-41-0;Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate;Adapalene Methyl Ester;Methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate;Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate;methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylate;W05XV3TPP3;methyl 6-(3-(1-adamantyl)-4-methoxyphenyl)-2-naphthoate;Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate (Adapalene Methyl Ester);2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-, methyl ester;Adapalene Related Compound B;C29H30O3;UNII-W05XV3TPP3;SCHEMBL641921;DTXSID00441277;FD7378;MFCD08063923;AKOS015851510;AKOS015895357;AC-3392;AS-16094;CS-0150365;FT-0642627;J3.522.343F;C71262;A801484;Q-101320;Methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2naphthoate;Methyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate;Methyl6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate;Methyl 3-O-(N-Acetyl-?-D-glucosaminyl)-?-D-galactopyranoside;methyl 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate;6-[3-(1-Adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid methyl ester;Methyl 6-(4-methoxy-3-tricyclo(3.3.1.13,7)dec-1-ylphenyl)-2-naphthalenecarboxylate;Methyl 6-[4-methoxy-3-(tricyclo[3.3.1.1~3,7~]decan-1-yl)phenyl]naphthalene-2-carboxylate;2-NAPHTHALENECARBOXYLIC ACID, 6-(4-METHOXY-3-TRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YLPHENYL)-, METHYL ESTER;2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo(3.3.1.13,7)dec-1-ylphenyl)-, methyl ester;METHYL 6-(4-METHOXY-3-TRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YLPHENYL)-2-NAPHTHALENECARBOXYLATE

Chemical Property of Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate

Chemical Property:

• Appearance/Colour: white to off white crystal
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 223-225°C
• Refractive Index: 1.627
• Boiling Point: 589.632 °C at 760 mmHg
• Flash Point: 258.722 °C
• PSA: 35.53000
• Density: 1.186 g/cm³
• LogP: 6.76980
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly)
• XLogP3: 8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 426.21949481
• Heavy Atom Count: 32
• Complexity: 659

Purity/Quality:

98% ^*data from raw suppliers

AdapaleneMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)OC)C45CC6CC(C4)CC(C6)C5
• Uses: Adapalene intermediate

Technology Process of Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoate

There total 24 articles about Methyl 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-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: 92.0%

3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6) + methyl 6-bromo-2-naphthoate (33626-98-1) → 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester (106685-41-0)

Guidance literature:

With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; water; Product distribution / selectivity; Inert atmosphere; Reflux;

Reference yield: 90.0%

3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6) + 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene (366799-67-9) → 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester (106685-41-0)

Guidance literature:

tris(3-hydroxypropyl)phosphine; nickel dichloride; In tetrahydrofuran; for 1h; Heating / reflux;

3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene; With water; potassium carbonate; In tetrahydrofuran; at 50 ℃; for 24h; Product distribution / selectivity; Heating / reflux;

Reference yield: 88.83%

methyl 6-bromo-2-naphthoate (33626-98-1) + 2-(1-adamantyl)-4-bromoanisole (104224-63-7) → 3,3'-diadamantyl-4,4'-dimethoxybiphenyl (932033-57-3) + 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester (106685-41-0)

Guidance literature:

2-(1-adamantyl)-4-bromoanisole; With magnesium; ethylene dibromide; In tetrahydrofuran; at 45 - 55 ℃; for 1.5h;

With zinc(II) chloride; In tetrahydrofuran; at 20 - 25 ℃; for 1h;

methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; at 20 ℃; for 2h;

upstream raw materials:

methyl 6-bromo-2-naphthoate

2-(1-adamantyl)-4-bromoanisole

4-bromo-phenol

1-adamanthanol

Downstream raw materials:

adapalene

Refernces

• 1、 Ju, Guodong,Yuan, Chunchen,Wang, Dongjie,Zhang, Jingyu,Zhao, Yingsheng. "A Direct Approach to Decoration of Bioactive Compounds via C-H Amination Reaction". . p. 9852 - 9855. Retrieved 2019/12/24.
• 2、 Nagaki,Hirose,Moriwaki,Mitamura,Matsukawa,Ishizuka,Yoshida. "Integration of borylation of aryllithiums and Suzuki-Miyaura coupling using monolithic Pd catalyst". . p. 4690 - 4694. Retrieved 2016/07/07.