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

Base Information

• Chemical Name: 1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenecarboxylic acid
• CAS No.: 69903-86-2
• Molecular Formula: C20H28O2
• Molecular Weight: 300.44
• Mol file: 69903-86-2.mol

Synonyms:veadeiroic acid;(4bS,8aS)-1-Ethyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-2-carboxylic acid;

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

Chemical Property:

• PSA: 37.30000
• LogP: 4.97740

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-phenanthrenecarboxylic acid

There total 23 articles about 1-Ethyl-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-phenanthrenecarboxylic acid 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 → (+/-)-veadeiroic acid (69903-86-2,111958-09-9)

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: KOH / methanol

With potassium hydroxide; sodium tetrahydroborate; methanesulfonic acid; hydrogen; phosphorus pentoxide; palladium on activated charcoal; In methanol; 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) → (+/-)-veadeiroic acid (69903-86-2,111958-09-9)

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: KOH / methanol

With potassium hydroxide; sodium tetrahydroborate; methanesulfonic acid; hydrogen; phosphorus pentoxide; palladium on activated charcoal; In methanol; 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) → (+/-)-veadeiroic acid (69903-86-2,111958-09-9)

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: KOH / methanol

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; methanesulfonic acid; hydrogen; phosphorus pentoxide; palladium on activated charcoal; In methanol; ethanol;

DOI:10.1039/P19930002223

upstream raw materials:

veadeiraldehyde

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

ethyllithium

methyl 2-ethyl-3-<2-(5'-hydroxy-2',6',6'-trimethylcyclohexyl)ethyl>benzoate

Downstream raw materials:

veadeirol

(+/-)-veadeirol

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.