7alpha-Acetoxyroyleanone

Base Information

• Chemical Name: 7alpha-Acetoxyroyleanone
• CAS No.: 6812-88-0
• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.477
• DSSTox Substance ID: DTXSID701316247
• Nikkaji Number: J16.091A
• Wikidata: Q104394696,Q105325613
• ChEMBL ID: CHEMBL516119
• Mol file: 6812-88-0.mol

Synonyms:7-acetylhorminone;7alpha-Acetoxyroyleanone;6812-88-0;Acetoxyroyleanone;7-Acetoxyroyleanon;CHEMBL516119;SCHEMBL22861892;DTXSID701316247;AKOS004901864

Chemical Property of 7alpha-Acetoxyroyleanone

Chemical Property:

• Vapor Pressure: 1.04E-10mmHg at 25°C
• Boiling Point: 467.6°Cat760mmHg
• Flash Point: 154.1°C
• PSA: 80.67000
• Density: 1.18g/cm³
• LogP: 4.07090
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 374.20932405
• Heavy Atom Count: 27
• Complexity: 783

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C2=C(C(=O)C1=O)C3(CCCC(C3CC2OC(=O)C)(C)C)C)O
• Isomeric SMILES: CC(C)C1=C(C2=C(C(=O)C1=O)[C@]3(CCCC([C@@H]3C[C@H]2OC(=O)C)(C)C)C)O

Technology Process of 7alpha-Acetoxyroyleanone

There total 5 articles about 7alpha-Acetoxyroyleanone 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:

12-benzoyloxy-11-hydroxyabieta-8,11,13-triene (62393-73-1) → 7-acetylhorminone (6812-88-0,77794-82-2,107664-07-3)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / butan-2-one

2: Pb(OAc)4

3: CrO₃, AcOH

4: (i) aq. NaHCO₃, MeOH, (ii) aq. HCl

With chromium(VI) oxide; lead(IV) acetate; potassium carbonate; acetic acid; In butanone;

DOI:10.1246/bcsj.52.1459

Reference yield:

12-Benzyloxy-11-methoxyabieta-8,11,13-trien (62393-75-3) → 7-acetylhorminone (6812-88-0,77794-82-2,107664-07-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Pb(OAc)4

2: CrO₃, AcOH

3: (i) aq. NaHCO₃, MeOH, (ii) aq. HCl

With chromium(VI) oxide; lead(IV) acetate; acetic acid;

DOI:10.1246/bcsj.52.1459

Reference yield:

7α-Acetoxy-12-benzoyloxy-11-methoxyabieta-8,11,13-trien (62393-80-0,62393-81-1) → 7-acetylhorminone (6812-88-0,77794-82-2,107664-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃, AcOH

2: (i) aq. NaHCO₃, MeOH, (ii) aq. HCl

With chromium(VI) oxide; acetic acid;

DOI:10.1246/bcsj.52.1459

upstream raw materials:

7α-Acetoxy-12-benzoyloxyabieta-8,12-dien-11,14-dion

12-Benzyloxy-11-methoxyabieta-8,11,13-trien

7α-Acetoxy-12-benzoyloxy-11-methoxyabieta-8,11,13-trien

12-benzoyloxy-11-hydroxyabieta-8,11,13-triene

Downstream raw materials:

royleanone

horminone

7-oxo-12-methoxy-6,11,14-trihydroxy-abieta-5,8,11-13-tetraene

6-oxo-11,12,14-trimethoxy-abieta-8,11,13-triene

Refernces

10.1246/bcsj.52.1459

Takashi Matsumoto and Shogo Harada details the total synthesis of several naturally occurring tricyclic diterpenes with an abietane skeleton. The authors describe the synthesis of (+)-taxoquinone, (-)-7a-acetoxyroyleanone, (-)-dehydroroyleanone, (-)-horminone, (-)-7-oxoroyleanone, and (+)-inuroyleanol, all starting from (+)-ferruginol. The synthesis involves various chemical transformations, including methylation, oxidation with chromium trioxide, reduction with sodium borohydride, acetylation, and other reactions. The structures of the synthesized compounds were confirmed through NMR spectroscopy and other analytical methods. The study represents a significant advancement in the field of natural product synthesis, providing detailed procedures and characterizations for these complex diterpenes.