1-[12-methoxypodocarpa-8(14),9(11),12-trien-13-yl]ethanone

Base Information

• Chemical Name: 1-[12-methoxypodocarpa-8(14),9(11),12-trien-13-yl]ethanone
• CAS No.: 19889-21-5
• Molecular Formula: C20H28O2
• Molecular Weight: 300.441
• Mol file: 19889-21-5.mol

Synonyms:

Chemical Property of 1-[12-methoxypodocarpa-8(14),9(11),12-trien-13-yl]ethanone

Chemical Property:

• Vapor Pressure: 3.44E-07mmHg at 25°C
• Boiling Point: 417.8°Cat760mmHg
• Flash Point: 166.8°C
• Density: 1.011g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[12-methoxypodocarpa-8(14),9(11),12-trien-13-yl]ethanone

There total 2 articles about 1-[12-methoxypodocarpa-8(14),9(11),12-trien-13-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:

(E)-geranic acid (4698-08-2) → 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone (19889-21-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: H₃PO₄ / toluene / 2 h / 100 °C

1.2: (-)-α-methylbenzylamine

2.1: 90 percent / K₂CO₃ / acetone / 3 h / 20 °C

3.1: 90 percent / LiAlH₄ / diethyl ether / 1 h / -10 °C

4.1: 75 percent / 4A molecular sieves; NaOAc; PCC / CH₂Cl₂ / 1 h / -10 °C

5.1: n-BuLi / hexane / 1 h / 20 °C

5.2: 60 percent / hexane / 4 h

6.1: 95 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C

7.1: 85 percent / BF₃*Et₂O / CH₂Cl₂

8.1: 95 percent / AlCl₃ / CH₂Cl₂ / -5 °C

With lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; phosphoric acid; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium acetate; potassium carbonate; pyridinium chlorochromate; palladium on activated charcoal; In diethyl ether; ethanol; hexane; dichloromethane; acetone; toluene; 1.1: Cyclization / 1.2: racemate resolution / 2.1: Methylation / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation / 6.1: Catalytic hydrogenation / 7.1: Cyclization / 8.1: Acetylation;

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

upstream raw materials:

(E)-geranic acid

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

Downstream raw materials:

(+/-)-ferruginol

nimbidiol

16-acetoxy-12-benzoyloxyabieta-8,11,13-trien-11-ol

(+/-)-nimbidiol

Refernces

• 1、 Gan, Yonghong,Li, Anpai,Pan, Xinfu,Chan, Albert S. C.,Yang, Teng-Kuei. "Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether". . p. 781 - 787. Retrieved 2007/10/03.