1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone

Base Information

• Chemical Name: 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone
• CAS No.: 121703-00-2
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• Mol file: 121703-00-2.mol

Synonyms:

Chemical Property of 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone

There total 1 articles about 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone 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:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone (19889-21-5,100170-42-1,113349-88-5,121703-00-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 89 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 68 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

3.1: 65.2 percent / BF₃*OEt₂ / nitromethane / 4 h / 20 °C

4.1: aq. KOH / ethanol / 10 h / Heating

5.1: 42 percent / Pb(OAc)4; Cu(OAc)2 / pyridine / 6 h / 150 °C

6.1: 85 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 20 °C

7.1: 87 percent / AlCl₃ / CH₂Cl₂ / 1.5 h / 20 °C

With lead(IV) acetate; dmap; potassium hydroxide; aluminium trichloride; copper diacetate; boron trifluoride diethyl etherate; hydrogen; dicyclohexyl-carbodiimide; lithium diisopropyl amide; 5percent Pd/C; In tetrahydrofuran; pyridine; nitromethane; ethanol; hexane; dichloromethane; ethyl acetate; 1.1: Metallation / 1.2: Alkylation / 2.1: Esterification / 3.1: Cyclization / 4.1: Hydrolysis / 5.1: Decarboxylation / 6.1: Hydrogenation / 7.1: Acetylation;

DOI:10.1039/b003497p

Reference yield:

1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone (19889-21-5,100170-42-1,113349-88-5,121703-00-2) → 12-methoxy-6,7-secoabieta-8,11,13-triene-6,7-dial

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / diethyl ether; tetrahydrofuran / 4 h / 0 °C

2.1: 92 percent / hydrogen; acetic acid / Pd/C / methanol / 8 h / 50 °C

3.1: 76 percent / chromium trioxide; acetic acid / 2 h / 20 °C

4.1: 99 percent / sodium borohydride / methanol / 13 h / 20 °C

5.1: 99 percent / p-toluenesulfonic acid / benzene / 1 h / Heating

6.1: ozone / CH₂Cl₂ / -78 °C

6.2: 70 percent / triphenylphosphine / CH₂Cl₂ / 3 h / -78 - 20 °C

With chromium(VI) oxide; sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; ozone; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1016/j.bmc.2007.01.031

Reference yield:

1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone (19889-21-5,100170-42-1,113349-88-5,121703-00-2) → 12-acetoxy-6,7-secoabieta-8,11,13-triene-6,7-dial

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / diethyl ether; tetrahydrofuran / 4 h / 0 °C

2.1: 92 percent / hydrogen; acetic acid / Pd/C / methanol / 8 h / 50 °C

3.1: 76 percent / chromium trioxide; acetic acid / 2 h / 20 °C

4.1: 99 percent / sodium borohydride / methanol / 13 h / 20 °C

5.1: 99 percent / p-toluenesulfonic acid / benzene / 1 h / Heating

6.1: 100 percent / dodecanethiol; n-butyllithium / hexamethylphosphoric acid triamide / 5 h / 100 °C

7.1: 98 percent / 4-(dimethylamino)pyridine; pyridine / 6 h / 20 °C

8.1: ozone / CH₂Cl₂ / -78 °C

8.2: 81 percent / triphenylphosphine / CH₂Cl₂ / 2 h / -78 - 20 °C

With pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; n-butyllithium; hydrogen; toluene-4-sulfonic acid; ozone; acetic acid; 1-dodecylthiol; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; benzene;

DOI:10.1016/j.bmc.2007.01.031

upstream raw materials:

1-chloro-3,7-dimethylocta-2,6-diene

Downstream raw materials:

(+/-)-ferruginol

(+/-)-nimbidiol

sugiol

Refernces