Schweinfurthin C

Base Information

• Chemical Name: Schweinfurthin C
• CAS No.: 217476-94-3
• Molecular Formula: C34H44O4
• Molecular Weight: 516.7108
• NSC Number: 698298
• DSSTox Substance ID: DTXSID70417727
• Nikkaji Number: J1.033.426H
• Metabolomics Workbench ID: 143788
• Mol file: 217476-94-3.mol

Synonyms:schweinfurthin C

Chemical Property of Schweinfurthin C

Chemical Property:

• Vapor Pressure: 1.09E-20mmHg at 25°C
• Boiling Point: 707.6°Cat760mmHg
• Flash Point: 288.9°C
• Density: 1.099g/cm³
• XLogP3: 10.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 516.32395988
• Heavy Atom Count: 38
• Complexity: 844

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCC1=C(C(=CC(=C1)C=CC2=CC(=C(C(=C2)O)CC=C(C)CCC=C(C)C)O)O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC1=C(C(=CC(=C1)/C=C/C2=CC(=C(C(=C2)O)C/C=C(\C)/CCC=C(C)C)O)O)O)/C)C

Technology Process of Schweinfurthin C

There total 14 articles about Schweinfurthin C 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: 51.0%

tetrakis(methoxymethyl)schweinfurtin C (252679-64-4) → schweinfurtin C (217476-94-3)

Guidance literature:

With hydrogenchloride; In methanol; for 0.4h; Heating;

DOI:10.1021/jo9908795

Reference yield:

3-bromo-4,5-dihydroxybenzaldehyde (16414-34-9) → schweinfurtin C (217476-94-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 69 percent / DIPEA / dimethylformamide / 28 h / 0 - 20 °C

2: 76 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

3: 99 percent / imidazole / CH₂Cl₂ / 22 h / 0 °C

4: 54 percent / n-BuLi / diethyl ether; hexane / 6 h / -78 - 20 °C

5: 96 percent / TBAF / tetrahydrofuran / 5 h / 0 °C

6: 59 percent / NaH / tetrahydrofuran / Heating

7: 51 percent / aq. HCl / methanol / 0.4 h / Heating

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Reduction / 3: Substitution / 4: Alkylation / 5: Substitution / 6: Wittig reaction / 7: Hydrolysis;

DOI:10.1021/jo9908795

Reference yield:

[3,5-bis(methoxymethoxy)phenyl]methanol (76280-60-9) → schweinfurtin C (217476-94-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / imidazole / CH₂Cl₂ / 12 h

2: 73 percent / n-BuLi; TMEDA; CuCN / hexane; tetrahydrofuran / -78 - 20 °C

3: 86 percent / TBAH / tetrahydrofuran / 3 h / 20 °C

4: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: 937 mg / NaI / acetone / 22 h / 20 °C

6: 100 percent / 2.5 h / Heating

7: 59 percent / NaH / tetrahydrofuran / Heating

8: 51 percent / aq. HCl / methanol / 0.4 h / Heating

With 1H-imidazole; hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetra(n-butyl)ammonium hydroxide; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; 1: Substitution / 2: Alkylation / 3: Substitution / 4: Substitution / 5: Substitution / 6: Arbuzov reaction / 7: Wittig reaction / 8: Hydrolysis;

DOI:10.1021/jo9908795

upstream raw materials:

tetrakis(methoxymethyl)schweinfurtin C

3-bromo-4,5-dihydroxybenzaldehyde

[3,5-bis(methoxymethoxy)phenyl]methanol

3-bromo-4,5-bis(methoxymethoxy)benzaldehyde