7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene

Base Information

• Chemical Name: 7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene
• CAS No.: 134435-55-5
• Molecular Formula: C₂₇H₃₄O₃S
• Molecular Weight: 438.631
• Mol file: 134435-55-5.mol

Synonyms:7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene

Chemical Property of 7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene

There total 22 articles about 7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene 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: 92.0%

7-Isopropyl-6-methoxy-1,1,4a-trimethyl-2-phenylsulfanyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (134435-53-3) → 2-Benzenesulfinyl-7-isopropyl-6-methoxy-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (134435-55-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃;

DOI:10.1080/00397919108020799

Reference yield: 92.0%

7-Oxo-3-phenylthio-12-methoxyabieta-8,11,13-triene (134435-53-3) → 7-Keto-3-phenylsulfinyl-12-methoxyabieta-8,11,13-triene (134435-55-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 1h;

Reference yield:

3-(1-methylethenyl)-4-methoxyphenylethyl acetate (134435-48-6) → 2-Benzenesulfinyl-7-isopropyl-6-methoxy-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (134435-55-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / H₂ / Pd/C / diethyl ether / 2068.6 Torr

2: 75 percent / PCC, HOAc, Celite, molecular sieve 4A / CH₂Cl₂

4: 84 percent / KBr, m-CPBA, 18-cr-6 / CH₂Cl₂ / 0.5 h / 0 °C

5: 98 percent / Mg / tetrahydrofuran

6: 97 percent / NaBH₄ / methanol / 0.2 h / Ambient temperature

7: 98 percent / PBr₃, pyridine / benzene / 3 h / Ambient temperature

8: 80 percent / 18-cr-6 / acetonitrile / 1 h / 60 °C

9: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, RT, 3 h

10: 1.) BF₃-CH₃NO₂ / 1.) nitromethane, -30 deg C, 2.25 min, 2.) nitromethane, -30 deg C, 2 h

11: 1.) LDA, O₂, 2.) 1M SnCl₂, 2M HCl / 1.) THF, -78 deg C, 1 h, 2.) THF, 0 deg C

12: 92 percent / m-CPBA / CH₂Cl₂ / -78 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; 18-crown-6 ether; 4 A molecular sieve; Celite; hydrogen; oxygen; phosphorus tribromide; boron trifluoride nitrometane adduct; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; tin(ll) chloride; potassium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;

DOI:10.1080/00397919108020799

upstream raw materials:

7-Isopropyl-6-methoxy-1,1,4a-trimethyl-2-phenylsulfanyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

o-isopropylanisole

4-bromo-2-isopropylanisole

4-Methoxy-3-isopropylbenzyl alcohol

Downstream raw materials:

12-hydroxy-abieta-8,11,13-trien-3,7-dione

3,7-Diketo-12-hydroxyabieta-8,11,13-triene

7-Keto-3-phenylthio-12-methoxyabieta-2,8,11,13-tetraene

7-Isopropyl-6-methoxy-1,1,4a-trimethyl-2-phenylsulfanyl-4,4a,10,10a-tetrahydro-1H-phenanthren-9-one

Refernces

• 1、 Burnell,Caron. "Synthesis of aromatic diterpenes synthesis of 12-hydroxy-abieta-8,11,13-trien-3,7-dione". . p. 127 - 132. Retrieved 2007/10/02.