Dehydrocurvularin

Base Information

• Chemical Name: Dehydrocurvularin
• CAS No.: 21178-57-4
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Hs Code.: 2932999099
• UNII: PAU7YA7FF9
• DSSTox Substance ID: DTXSID101017526
• Nikkaji Number: J1.002.893K,J3.505.575D
• Wikipedia: Dehydrocurvularin
• Wikidata: Q15410896
• ChEMBL ID: CHEMBL520014
• Mol file: 21178-57-4.mol

Synonyms:10,11-dehydrocurvularin;curvularin

Chemical Property of Dehydrocurvularin

Chemical Property:

• Vapor Pressure: 7.02E-14mmHg at 25°C
• Boiling Point: 576.3 ºC at 760 mm
• Flash Point: 216.7ºC
• PSA: 83.83000
• Density: 1.225 g/cm³
• LogP: 2.49480
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 290.11542367
• Heavy Atom Count: 21
• Complexity: 417

Purity/Quality:

99% ^*data from raw suppliers

[S-(E)]-4,5,6,7-Tetrahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC=CC(=O)C2=C(CC(=O)O1)C=C(C=C2O)O
• Isomeric SMILES: C[C@H]1CCC/C=C/C(=O)C2=C(CC(=O)O1)C=C(C=C2O)O
• Uses: [S-(E)]-4,5,6,7-Tetrahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione is a fungal nematocide from Aspergillus. [S-(E)]-4,5,6,7-Tetrahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione exhibits anticancer properties and may have applications related to cancer research and drug discovery.

Technology Process of Dehydrocurvularin

There total 4 articles about Dehydrocurvularin 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: 64.0%

(S,E)-11,13-dimethoxy-4-methyl-4,5,6,7-tetrahydro-1H-benzo[d][1]oxacyclododecine-2,10-dione (100905-80-4) → 10,11-dehydrocurvularin (21178-57-4)

Guidance literature:

With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide; In benzene; at 0 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.9b00776

Reference yield:

(S)-hept-6-en-2-yl 2-(3,5-dimethoxyphenyl)acetate → 10,11-dehydrocurvularin (21178-57-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tin(IV) chloride / dichloromethane / -78 - -40 °C / Inert atmosphere

1.2: 20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 45 °C / Inert atmosphere

3.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; aluminium(III) iodide; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; In dichloromethane; benzene; 1.1: |Friedel-Crafts Acylation;

DOI:10.1021/acs.joc.9b00776

Reference yield:

(S)-hept-6-en-2-ol (88980-13-6) → 10,11-dehydrocurvularin (21178-57-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: tin(IV) chloride / dichloromethane / -78 - -40 °C / Inert atmosphere

2.2: 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 45 °C / Inert atmosphere

4.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; aluminium(III) iodide; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; dicyclohexyl-carbodiimide; In dichloromethane; benzene; 2.1: |Friedel-Crafts Acylation;

DOI:10.1021/acs.joc.9b00776

upstream raw materials:

(S)-hept-6-en-2-ol

(S,E)-11,13-dimethoxy-4-methyl-4,5,6,7-tetrahydro-1H-benzo[d][1]oxacyclododecine-2,10-dione

Downstream raw materials:

10-dihydrocurvularin

curvularin

Refernces