Dihydroactinidiolide

Base Information

• Chemical Name: Dihydroactinidiolide
• CAS No.: 15356-74-8
• Deprecated CAS: 19432-05-4
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• European Community (EC) Number: 239-390-4,641-406-3
• NSC Number: 357087
• UNII: BH8469LVA9
• DSSTox Substance ID: DTXSID00864588
• Nikkaji Number: J99.559B
• Wikipedia: Dihydroactinidiolide
• Wikidata: Q27274663
• Metabolomics Workbench ID: 46888
• ChEMBL ID: CHEMBL2271411
• Mol file: 15356-74-8.mol

Synonyms:2-hydroxy-2,6,6-trimethylcyclohexylideneacetic acid gamma-lactone

Chemical Property of Dihydroactinidiolide

Chemical Property:

• Vapor Pressure: 0.00147mmHg at 25°C
• Melting Point: 42-43°
• Refractive Index: 1.504
• Boiling Point: 296.099 °C at 760 mmHg
• Flash Point: 120.249 °C
• PSA: 26.30000
• Density: 1.058 g/cm³
• LogP: 2.43840
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 180.115029749
• Heavy Atom Count: 13
• Complexity: 289

Purity/Quality:

99% ^*data from raw suppliers

4,4,7a-Trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1=CC(=O)O2)C)C

Technology Process of Dihydroactinidiolide

There total 34 articles about Dihydroactinidiolide 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: 92.0%

(2,6,6-trimethylcyclohex-1-enyl)acetic acid (472-68-4) → (+/-)-dihydroactinidiolide (15356-74-8,17092-92-1,19432-05-4,81800-41-1)

Guidance literature:

With diphenyl diselenide; tetraethylammonium bromide; water; sodium carbonate; In acetonitrile; for 0.6h; Ambient temperature; electrolysis under a constant current 70 mA;

DOI:10.1021/ja00405a064

Reference yield: 90.0%

(3AR,7AS)-2-oxo-3-phenylselenyl-4,4,7a-trimethyloctahydrobenzofuran (104446-40-4) → (+/-)-dihydroactinidiolide (15356-74-8,17092-92-1,19432-05-4,81800-41-1)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; acetic acid; at 0 - 20 ℃; for 4.5h;

DOI:10.1016/j.tetlet.2009.07.067

Reference yield: 87.0%

2,2-Diethoxy-4,4,7a-trimethyl-4,5,6,7,7a-pentahydro-2H-benzofuran (120211-66-7) → (+/-)-dihydroactinidiolide (15356-74-8,17092-92-1,19432-05-4,81800-41-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; water; for 2h;

DOI:10.1016/S0040-4020(01)86013-0

upstream raw materials:

4,4,7a-trimethylhexahydro-1-benzofuran-2(3H)-one

(+/-)-aeginetolide

(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

(2,6,6-trimethylcyclohex-1-enyl)acetic acid

Downstream raw materials:

C₁₁H₂₀O₂