1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenemethanol

Base Information

• Chemical Name: 1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenemethanol
• CAS No.: 69940-49-4
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.458
• Mol file: 69940-49-4.mol

Synonyms:2-Phenanthrenemethanol,1-ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-, (4bS-trans)-; Veadeirol

Chemical Property of 1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenemethanol

Chemical Property:

• PSA: 20.23000
• LogP: 4.77150

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenemethanol

There total 21 articles about 1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenemethanol 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:

2-Ethyl-3-[(E)-2-(2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-vinyl]-benzoic acid → (+/-)-veadeirol (69940-49-4,111958-10-2)

Guidance literature:

Multi-step reaction with 5 steps

2: 97 percent / H₂ / Pd/C / methanol / 6 h / Ambient temperature

3: NaBH₄ / ethanol

4: P₂O₅, MeSO₃H / 2 h / 30 °C

5: 0.28 g / LiAlH₄ / diethyl ether

With sodium tetrahydroborate; lithium aluminium tetrahydride; methanesulfonic acid; hydrogen; phosphorus pentoxide; palladium on activated charcoal; In methanol; diethyl ether; ethanol;

DOI:10.1039/P19930002223

Reference yield:

methyl 2-ethyl-3-<2-(2',6',6'-trimethyl-3'-oxocyclohex-1-enyl)vinyl>benzoate (136063-26-8) → (+/-)-veadeirol (69940-49-4,111958-10-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / Pd/C / methanol / 6 h / Ambient temperature

2: NaBH₄ / ethanol

3: P₂O₅, MeSO₃H / 2 h / 30 °C

4: 0.28 g / LiAlH₄ / diethyl ether

With sodium tetrahydroborate; lithium aluminium tetrahydride; methanesulfonic acid; hydrogen; phosphorus pentoxide; palladium on activated charcoal; In methanol; diethyl ether; ethanol;

DOI:10.1039/P19930002223

Reference yield:

3-<2-<3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-2-ethylphenyl>vinyl>-2,4,4-trimethylcyclohex-2-enone (136063-25-7) → (+/-)-veadeirol (69940-49-4,111958-10-2)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. HCl / 0.5 h / Heating

3: 97 percent / H₂ / Pd/C / methanol / 6 h / Ambient temperature

4: NaBH₄ / ethanol

5: P₂O₅, MeSO₃H / 2 h / 30 °C

6: 0.28 g / LiAlH₄ / diethyl ether

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; methanesulfonic acid; hydrogen; phosphorus pentoxide; palladium on activated charcoal; In methanol; diethyl ether; ethanol;

DOI:10.1039/P19930002223

upstream raw materials:

(4bS,8aS)-1-Ethyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-2-carboxylic acid methyl ester

veadeiroic acid

13-Methoxycarbonyl-14-ethylpodocarpa-8,11,13-trien

(+/-)-veadeiroic acid

Refernces

• 1、 Saha, Arabinda,Nasipuri, Dhanonjoy. "Stereoselective Synthesis of (+/-)-Veadeiroic Acid and (+/-)-Veadeirol by Cyclisation of a 2-(2-Arylethyl)-1,3,3-trimethylcyclohexyl Cation: Mechanism and Stereochemistry of Related Cycloalkylation Reactions". . p. 2223 - 2228. Retrieved 2007/10/02.
• 2、 Saha, Arabinda,Mahapatra, Bimal,Nasipuri, Dhanonjoy. "Birch reduction of 14-methoxypodocarpa-8,11,13-triene and a stereoselective synthesis of veadeiroic acid and veadeirol - Two novel diterpenes with cleistanthane skeleton". . p. 721 - 722. Retrieved 2007/10/02.