3-(Acetyloxy)carda-14,20(22)-dienolide

Base Information

• Chemical Name: 3-(Acetyloxy)carda-14,20(22)-dienolide
• CAS No.: 4240-51-1
• Molecular Formula: C25H34O4
• Molecular Weight: 398.543
• NSC Number: 137447
• DSSTox Substance ID: DTXSID60300518
• Mol file: 4240-51-1.mol

Synonyms:4240-51-1;3-(acetyloxy)carda-14,20(22)-dienolide;NSC137447;DTXSID60300518;NSC-137447

Chemical Property of 3-(Acetyloxy)carda-14,20(22)-dienolide

Chemical Property:

• Vapor Pressure: 8.78E-12mmHg at 25°C
• Boiling Point: 541.3°Cat760mmHg
• Flash Point: 270.9°C
• Density: 1.16g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 398.24570956
• Heavy Atom Count: 29
• Complexity: 795

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C(C1)CCC3C2CCC4(C3=CCC4C5=CC(=O)OC5)C)C

Technology Process of 3-(Acetyloxy)carda-14,20(22)-dienolide

There total 17 articles about 3-(Acetyloxy)carda-14,20(22)-dienolide 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%

digitoxigenin 3-acetate (808-19-5) → 3β-acetoxy-5β-carda-14,20(22)-dienolide (4240-51-1)

Guidance literature:

With tetrachloromethane; triphenylphosphine; In acetonitrile; at 50 ℃; for 24h;

Reference yield: 17.0%

digitoxigenin 3-acetate (808-19-5) → 3-O-Acetyl-14-deoxy-14-fluorodigitoxigenin (77727-21-0) + 3β-acetoxy-5β-carda-14,20(22)-dienolide (4240-51-1)

Guidance literature:

With potassium fluoride; sulfur tetrafluoride; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1002/cber.19811140334

Reference yield:

(+)-digitoxigenin (143-62-4) → 3β-acetoxy-5β-carda-14,20(22)-dienolide (4240-51-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / (i-C₄H₉)2AlH / tetrahydrofuran / 1.) -30 deg C to -35 deg C, 1 h, 2.) up to 0 deg C during 30 min

2: 4-(N,N-dimethylamino)pyridine / pyridine / 144 h / Ambient temperature

3: 130 mg / silicagel H / CH₂Cl₂ / 18 h

4: 67.3 percent / Jones's reagent / acetone / 0.17 h / 0 °C

5: NaBH₄ / methanol / 0.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; Jones's reagent; silica gel; diisobutylaluminium hydride; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone;

upstream raw materials:

3β-Acetoxy-21ξ-hydroxy-5β-carda-14,20(22)-dienolid

digitoxigenin 3-acetate

acetic anhydride

pyridine

Downstream raw materials:

digitoxigenin 3-acetate

Refernces

• 1、 Lindig, Claus,Repke, Kurt R. H.. "Partial Syntheses of Cardenolides and Cardenolide-Analogues. XII. Synthesis of 21-Substituted Cardenolides by Oxidation of 17β-(3-Furyl)-Steroids and Nucleophilic Substitution". . p. 841 - 858. Retrieved 2007/10/02.
• 2、 Theil, Fritz,Lindig, Claus,Repke, Kurt. "Regioselektive Dehydratisierung tertiaerer Alkohole mit Triphenylphosphin/Tetrachlormethan". . p. 372 - 373. Retrieved 2007/10/02.