Frenolicin

Base Information

• Chemical Name: Frenolicin
• CAS No.: 10023-07-1
• Molecular Formula: C₁₈H₁₈O₇
• Molecular Weight: 346.337
• UNII: H1POH9E7JP
• DSSTox Substance ID: DTXSID20433578
• Nikkaji Number: J15.788K
• Wikidata: Q27279511
• Metabolomics Workbench ID: 128941
• ChEMBL ID: CHEMBL2409149
• Mol file: 10023-07-1.mol

Synonyms:frenolicin;frenolicin B

Chemical Property of Frenolicin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 655.774°C at 760 mmHg
• Flash Point: 243.284°C
• Density: 1.51g/cm³
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 346.10525291
• Heavy Atom Count: 25
• Complexity: 631

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1C23C(=O)C4=C(C=CC=C4O)C(=O)C2(O3)CC(O1)CC(=O)O
• Isomeric SMILES: CCC[C@@H]1[C@]23C(=O)C4=C(C=CC=C4O)C(=O)[C@]2(O3)C[C@H](O1)CC(=O)O

Technology Process of Frenolicin

There total 14 articles about Frenolicin 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:

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol (73794-56-6,77448-22-7) → (+/-)-frenolicin (10023-07-1,73804-51-0,77448-38-5,77549-95-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 60.9 percent / n-Buli / dimethylsulfoxide / 2 h / Ambient temperature

2: 98.2 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

3: 80 percent / DDQ, TsOH / methanol / Heating; 9h, addn. of dioxane, 12h

4: KOH / methanol; H₂O

5: 1.) t.BuOOh, Triton B / 1.) dioxane, ethanol, r.t.

6: KOH / methanol; H₂O / Ambient temperature

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)92203-2

Reference yield:

frenolicin F (1450893-33-0) → (-)-frenolicin (10023-07-1,73804-51-0,77448-38-5,77549-95-2)

Guidance literature:

With Dess-Martin periodane; In chloroform-d1; at 20 ℃; for 0.166667h;

DOI:10.1021/np400231r

Reference yield:

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol (73794-56-6,77448-22-7) → (+/-)-epifrenolicin (10023-07-1,73804-51-0,77448-38-5,77549-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 60.9 percent / n-Buli / dimethylsulfoxide / 2 h / Ambient temperature

2: 98.2 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

3: 80 percent / DDQ, TsOH / methanol / Heating; 9h, addn. of dioxane, 12h

4: KOH / methanol; H₂O

5: t-BuOOH, Triton B / dioxane; H₂O / Ambient temperature

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)92203-2

upstream raw materials:

(+/-)-deoxyfrenolicin

(+/-)-frenolicin methyl ester

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol

((7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-7-oxo-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracen-9-yl)-acetic acid methyl ester

Downstream raw materials:

Deoxyfrenolicin

Refernces

• 1、 Ichihara, Akitami,Ubukata, Makoto,Oikawa, Hideaki,Murakami, Kazuo,Sakamura, Sadao. "TOTAL SYNTHESIS OF (+-)-NANAOMYCIN A AND (+-)-FRENOLICIN". . p. 4469 - 4472. Retrieved 2007/10/02.