Cyperolone

Base Information

• Chemical Name: Cyperolone
• CAS No.: 13741-46-3
• Molecular Formula: C15H24O2
• Molecular Weight: 236.34986
• DSSTox Substance ID: DTXSID90415700
• Nikkaji Number: J14.923C
• Wikidata: Q27149856
• Mol file: 13741-46-3.mol

Synonyms:cyperolone

Chemical Property of Cyperolone

Chemical Property:

• PSA: 37.30000
• LogP: 3.09900
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(CCC(C2(C1)C(=O)C)O)C
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2(CC[C@@H]([C@]2(C1)C(=O)C)O)C

Technology Process of Cyperolone

There total 22 articles about Cyperolone 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: 44.0%

(1S,3aS,6R,7aS)-7a-ethinyl-3a-methyl-6-(prop-1-en-2-yl)octahydro-1H-inden-1-ol (1359761-38-8) → (3aS,5aS,8R,9aR)-8-(prop-1-en-2-yl)-5a-methyloctahydroindeno[1,7a-b]furan-2-one (1359761-39-9) + (+)-cyperolone (18318-53-1,13741-46-3)

Guidance literature:

With sulfuric acid; water; mercury(II) oxide; In acetone; at 23 ℃; for 20h;

DOI:10.1021/ol300058t

Reference yield:

trans-(5R)-1-(hydroxymethyl)-5-isopropenyl-2-methylcyclohex-2-ene-1-ol → (3aS,5aS,8R,9aR)-8-(prop-1-en-2-yl)-5a-methyloctahydroindeno[1,7a-b]furan-2-one (1359761-39-9) + (+)-cyperolone (18318-53-1,13741-46-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 54 h / 23 °C

3.1: iodine; magnesium; mercury dichloride / diethyl ether; toluene / 20 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 20 °C

5.1: platinum(IV) chloride; isopropyl alcohol; cyclo-octa-1,5-diene / toluene / 0.33 h / 23 °C

6.1: toluene-4-sulfonic acid / tetrahydrofuran / 20 h / 65 °C

7.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.67 h / 0 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / dichloromethane / 40 h / 23 °C

9.1: bis(acetylacetonate)oxovanadium / dichloromethane / 23 °C

9.2: 25 h / 23 °C

10.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 27 h / 23 °C

11.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -78 °C

11.2: 8 h / -78 - -20 °C

12.1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere

13.1: sulfuric acid; water; mercury(II) oxide / acetone / 20 h / 23 °C

With 1H-imidazole; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; iodine; sulfur trioxide pyridine complex; platinum(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; cyclo-octa-1,5-diene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ol300058t

Reference yield:

(S)-2-methyl-5-(prop-1-en-2-yl)-3-(((triisopropylsilyl)oxy)methyl)cyclohex-2-enone (1359761-28-6) → (3aS,5aS,8R,9aR)-8-(prop-1-en-2-yl)-5a-methyloctahydroindeno[1,7a-b]furan-2-one (1359761-39-9) + (+)-cyperolone (18318-53-1,13741-46-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: iodine; magnesium; mercury dichloride / diethyl ether; toluene / 20 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 20 °C

3.1: platinum(IV) chloride; isopropyl alcohol; cyclo-octa-1,5-diene / toluene / 0.33 h / 23 °C

4.1: toluene-4-sulfonic acid / tetrahydrofuran / 20 h / 65 °C

5.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.67 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / dichloromethane / 40 h / 23 °C

7.1: bis(acetylacetonate)oxovanadium / dichloromethane / 23 °C

7.2: 25 h / 23 °C

8.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 27 h / 23 °C

9.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -78 °C

9.2: 8 h / -78 - -20 °C

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere

11.1: sulfuric acid; water; mercury(II) oxide / acetone / 20 h / 23 °C

With 1H-imidazole; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; iodine; sulfur trioxide pyridine complex; platinum(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; mercury dichloride; mercury(II) oxide; cyclo-octa-1,5-diene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ol300058t

upstream raw materials:

3-Epi-cyperolon

3β-Acetoxy-cyper-11-en-4-on (Cyperolon-acetat)

3α-Acetoxy-cyper-11-en-4-on

3β-Acetoxy-cyper-11-en-4ξ-ol

Refernces

• 1、 Hikino,Suzuki,Takemoto. "Synthesis of cyperolone and 3-epi-cyperolone.". . p. 1395 - 1404. Retrieved 2007/10/10.