1-Naphthalenecarboxylic acid, 1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6-(phenylseleno)-, ethyl ester

Base Information

• Chemical Name: 1-Naphthalenecarboxylic acid, 1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6-(phenylseleno)-, ethyl ester
• CAS No.: 95695-13-9
• Molecular Formula: C23H32O2Se
• Molecular Weight: 419.466
• Mol file: 95695-13-9.mol

Synonyms:

Chemical Property of 1-Naphthalenecarboxylic acid, 1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6-(phenylseleno)-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Naphthalenecarboxylic acid, 1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6-(phenylseleno)-, ethyl ester

There total 1 articles about 1-Naphthalenecarboxylic acid, 1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6-(phenylseleno)-, ethyl ester 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:

diphenyl diselenide (1666-13-3) + ethyl (2Z/E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate (33776-65-7) → 2,5,5,8a-Tetramethyl-6-phenylselanyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester (95695-13-9)

Guidance literature:

With mercury(II) trifluoroacetate; Yield given. Multistep reaction; 1.) nitromethane, -5 degC, 5 min; 2.) benzene, irradiation, 5 min;

DOI:10.1021/ja00295a025

Reference yield:

2,5,5,8a-Tetramethyl-6-phenylselanyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester (95695-13-9) → 3-Hydroxy-5-methoxy-4-(2,5,5,8a-tetramethyl-3,4,4a,5,8,8a-hexahydro-naphthalen-1-ylmethyl)-benzene-1,2-dicarbaldehyde (911794-92-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / sodium periodate / tetrahydrofuran; H₂O / 12 h / Ambient temperature

2: 90 percent / potassium hydride / 1,2-dimethoxy-ethane / 0.5 h / 60 °C

3: 74 percent / lithium aluminum hydride / diethyl ether / 15 h / 23 °C

4: phosphorus tribromide / diethyl ether / 0.17 h / 0 °C

5: tetramethylethylenediamine, n-butyllithium / hexane / 15 h / Ambient temperature

6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

7: 280 mg / 1.) oxalyl chloride, dimethyl sulfoxide; 2.) triethylamine / CH₂Cl₂ / 1.) -78 degC, 45 min; 2.) room t., 1.3 h

8: acetic acid / tetrahydrofuran; H₂O / 13 h / Ambient temperature

With sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; phosphorus tribromide; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water;

DOI:10.1021/ja00295a025

Reference yield:

2,5,5,8a-Tetramethyl-6-phenylselanyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid ethyl ester (95695-13-9) → [6-Hydroxymethyl-4-methoxy-2-(tetrahydro-pyran-2-yloxy)-3-(2,5,5,8a-tetramethyl-3,4,4a,5,8,8a-hexahydro-naphthalen-1-ylmethyl)-phenyl]-methanol

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / sodium periodate / tetrahydrofuran; H₂O / 12 h / Ambient temperature

2: 90 percent / potassium hydride / 1,2-dimethoxy-ethane / 0.5 h / 60 °C

3: 74 percent / lithium aluminum hydride / diethyl ether / 15 h / 23 °C

4: phosphorus tribromide / diethyl ether / 0.17 h / 0 °C

5: tetramethylethylenediamine, n-butyllithium / hexane / 15 h / Ambient temperature

6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

With sodium periodate; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; phosphorus tribromide; potassium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; water;

DOI:10.1021/ja00295a025

upstream raw materials:

diphenyl diselenide

ethyl (2Z/E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate

Downstream raw materials:

3-Hydroxy-5-methoxy-4-(2,5,5,8a-tetramethyl-3,4,4a,5,8,8a-hexahydro-naphthalen-1-ylmethyl)-benzene-1,2-dicarbaldehyde