(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene

Base Information

• Chemical Name: (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene
• CAS No.: 70614-86-7
• Molecular Formula: C₂₁H₃₀O
• Molecular Weight: 298.469
• Mol file: 70614-86-7.mol

Synonyms:(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene

Chemical Property of (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene

There total 1 articles about (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene 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:

(E)-geranic acid (4698-08-2) → (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene (70614-86-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: H₃PO₄ / toluene / 2 h / 100 °C

1.2: (-)-α-methylbenzylamine / diethyl ether; hexane

1.3: 90 percent / HCl / methanol

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

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

4.1: NaOAc; 4A m.s.; PCC / CH₂Cl₂ / 1 h / -10 °C

5.1: n-butyllithium / hexane / 1 h / 20 °C

5.2: hexane / 4 h / 20 °C

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

7.1: 85 percent / BF₃*Et₂O / CH₂Cl₂

8.1: 95 percent / AlCl₃ / CH₂Cl₂ / -10 - -5 °C

9.1: 95 percent / tetrahydrofuran / 4 h / 0 °C

10.1: 90 percent / p-TosOH / benzene / 0.5 h / Heating

11.1: 95 percent / H₂ / 5 percent Pd/C / ethanol / 20 °C

12.1: 90 percent / CrO₃ / acetic acid / 0.5 h / 20 °C

13.1: 95 percent / NaBH₄ / methanol / 1 h

14.1: p-Tos / benzene / 0.5 h / Heating

With chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; phosphoric acid; boron trifluoride diethyl etherate; hydrogen; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetic acid; acetone; toluene; benzene; 1.1: Cyclization / 1.2: Acylation / 1.3: Hydrolysis / 2.1: Esterification / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Substitution / 6.1: Catalytic hydrogenation / 7.1: Cyclization / 8.1: Acetylation / 9.1: Methylation / 10.1: Dehydration / 11.1: Catalytic hydrogenation / 12.1: Oxidation / 13.1: Reduction / 14.1: Dehydration;

DOI:10.1016/S0957-4166(00)00007-0

Reference yield: 70.0%

6,7-dehydroferruginyl methyl ether (64158-67-4,70614-86-7,94669-22-4) → 12-methoxy-6,7-secoabieta-8,11,13-triene-6,7-dial

Guidance literature:

6,7-dehydroferruginyl methyl ether; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 3h; Further stages.;

DOI:10.1016/j.bmc.2007.01.031

Reference yield: 70.0%

(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene (70614-86-7) → 6α-hydroxy-7-oxoferruginol (55898-07-2)

Guidance literature:

(4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene; With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 25 ℃; for 0.333333h;

With sodium thioethylate; In dichloromethane; N,N-dimethyl-formamide; acetone; at 90 ℃; for 8h;

DOI:10.1016/j.tetlet.2013.06.048

upstream raw materials:

(E)-geranic acid

Downstream raw materials:

(+/-)-12-Benzoyloxyabieta-8,11,13-trien-6β,11-diol

(+)-sugiol

5,6-dehydrosugiol

royleanone