Dehydrorotenone

Base Information

• Chemical Name: Dehydrorotenone
• CAS No.: 3466-09-9
• Molecular Formula: C23H20O6
• Molecular Weight: 392.408
• NSC Number: 194812
• Wikidata: Q27189544
• Metabolomics Workbench ID: 22708
• ChEMBL ID: CHEMBL3039287
• Mol file: 3466-09-9.mol

Synonyms:dehydrorotenone

Chemical Property of Dehydrorotenone

Chemical Property:

• Vapor Pressure: 1.76E-13mmHg at 25°C
• Boiling Point: 580.8°C at 760 mmHg
• Flash Point: 254.2°C
• PSA: 67.13000
• Density: 1.36g/cm³
• LogP: 4.24920
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 392.12598835
• Heavy Atom Count: 29
• Complexity: 729

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC

Technology Process of Dehydrorotenone

There total 17 articles about Dehydrorotenone 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: 27.0%

rotenone (83-79-4) → (2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one (34487-52-0) + 6a,12a-dehydrorotenone (3466-09-9)

Guidance literature:

With trimethylsilyl iodide; In chloroform; at 50 ℃; for 20h;

Reference yield: 24.0%

rotenone (83-79-4) → 6a,12a-dehydrorotenone (3466-09-9)

Guidance literature:

With manganese(IV) oxide; In acetone; for 3h; Heating;

Reference yield: 13.0%

→ 6a,12a-dehydrorotenone (3466-09-9)

Guidance literature:

With pyridine; iodine; at 10 ℃; for 0.5h; under 760.051 Torr;

at 170 ℃; for 0.045h; under 7500.75 Torr;

upstream raw materials:

Derritol

ethyl bromoacetate

Perbenzoic acid

chloroform

Downstream raw materials:

2-(2-hydroxy-4,5-dimethoxy-phenyl)-1-(4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-ethanone

9-hydroxy-8-isopentyl-2,3-dimethoxy-6H-chromeno[3,4-b]chromen-12-one

{2-[2-(4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid

{2-[2-((R)-4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid ethyl ester

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