methyl 12-acetylabieta-8(14),9(11),12-trien-18-oate

Base Information

• Chemical Name: methyl 12-acetylabieta-8(14),9(11),12-trien-18-oate
• CAS No.: 28625-40-3
• Molecular Formula: C23H32 O3
• Molecular Weight: 356.4984
• Mol file: 28625-40-3.mol

Synonyms:1-Phenanthrenecarboxylicacid, 6-acetyl-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-,methyl ester, [1R-(1a,4ab,10aa)]-; Podocarpa-8,11,13-trien-15-oic acid,12-acetyl-13-isopropyl-, methyl ester (8CI); 12-Acetyldehydroabietic acidmethyl ester; Methyl 12-acetyldehydroabietate; NSC 146203; NSC 2975

Chemical Property of methyl 12-acetylabieta-8(14),9(11),12-trien-18-oate

Chemical Property:

• Vapor Pressure: 9.08E-09mmHg at 25°C
• Boiling Point: 463.4°C at 760 mmHg
• Flash Point: 199°C
• Density: 1.046g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 12-acetylabieta-8(14),9(11),12-trien-18-oate

There total 13 articles about methyl 12-acetylabieta-8(14),9(11),12-trien-18-oate 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: 99.0%

Methyl dehydroabietate (1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7) + acetyl chloride (75-36-5) → methyl (1R,4aS,10aR)-6-acetyl-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenantrene-1-carboxylate (28625-40-3)

Guidance literature:

acetyl chloride; With aluminum (III) chloride; In tetrachloromethane; at -20 ℃; for 0.5h; Inert atmosphere;

Methyl dehydroabietate; In tetrachloromethane; at -20 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.10.018

Reference yield: 80.0%

Methyl dehydroabietate (1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7) → methyl (1R,4aS,10aR)-6-acetyl-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenantrene-1-carboxylate (28625-40-3)

Guidance literature:

With aluminum (III) chloride; In carbon disulfide; Reflux;

DOI:10.1016/j.bmcl.2008.08.078

Reference yield:

dehydroabietic acid (1740-19-8) → methyl (1R,4aS,10aR)-6-acetyl-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenantrene-1-carboxylate (28625-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 12 h / 90 °C

2: aluminum oxide / tetrachloromethane / 12 h / -10 - 20 °C / Inert atmosphere

With aluminum oxide; sulfuric acid; In tetrachloromethane;

upstream raw materials:

Methyl dehydroabietate

acetyl chloride

aluminium trichloride

nitrobenzene

Downstream raw materials:

(1R,4aS,10aR)-7-Isopropyl-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester

18-Hydroxyferruginol

(4aS,10aR)-7-Isopropyl-6-methoxy-4a-methyl-1-phenylsulfanylmethyl-3,4,4a,9,10,10a-hexahydro-phenanthrene

12-methoxy-abietatrien-(8.11.13)-oic acid-⁽¹⁸⁾

Refernces

• 1、 Liu, Ming-Liang,Pan, Xue-Ying,Yang, Teng,Zhang, Wen-Ming,Wang, Tian-Qi,Wang, He-Yun,Lin, Hai-Xia,Yang, Cai-Guang,Cui, Yong-Mei. "The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: Modifications at C-12". . p. 5492 - 5496. Retrieved 2016.
• 2、 Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe. "Late-stage C-H amination of abietane diterpenoids". supporting information. p. 4736 - 4746. Retrieved 2019/05/24.