3,4,5,4'-Tetramethoxystilbene

Base Information

• Chemical Name: 3,4,5,4'-Tetramethoxystilbene
• CAS No.: 134029-62-2
• Molecular Formula: C18H20O4
• Molecular Weight: 300.354
• NSC Number: 631365
• DSSTox Substance ID: DTXSID501300535
• Nikkaji Number: J1.693.898J,J1.958.288D
• ChEMBL ID: CHEMBL87982
• Mol file: 134029-62-2.mol

Synonyms:3,4,5,4'-tetramethoxy-trans-stilbene;3,4,5,4'-tetramethoxystilbene;DMU-212;trans-3,4,5,4'-tetramethoxystilbene

Chemical Property of 3,4,5,4'-Tetramethoxystilbene

Chemical Property:

• Melting Point: 157-159 °C
• Boiling Point: 444.027 °C at 760 mmHg
• Flash Point: 144.057 °C
• PSA: 36.92000
• Density: 1.118 g/cm³
• LogP: 3.89140
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 300.13615911
• Heavy Atom Count: 22
• Complexity: 322

Purity/Quality:

99%, ^*data from raw suppliers

(E)-3,4,5,4′-Tetramethoxystilbene ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C2=CC(=C(C(=C2)OC)OC)OC

Technology Process of 3,4,5,4'-Tetramethoxystilbene

There total 69 articles about 3,4,5,4'-Tetramethoxystilbene 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: 93.0%

4-Methoxystyrene (637-69-4,24936-44-5) + 3,4,5-trimethoxybenzenediazonium tetrafluoroborate → (E)-3,4,4',5-tetramethoxystilbene (134029-62-2)

Guidance literature:

With Pd₂(dba)4; sodium acetate; In benzonitrile; at 25 ℃; for 0.3h;

DOI:10.1016/j.tetlet.2008.07.087

Reference yield: 89.0%

trans-3,4',5-trimethoxy-4-hydroxystilbene (746636-48-6) + methyl iodide (74-88-4) → (E)-3,4,4',5-tetramethoxystilbene (134029-62-2)

Guidance literature:

trans-3,4',5-trimethoxy-4-hydroxystilbene; With potassium tert-butylate; In N,N-dimethyl-formamide;

methyl iodide; In N,N-dimethyl-formamide; at 80 ℃; for 1h;

Reference yield: 89.0%

1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetylene (208347-68-6) → (E)-3,4,4',5-tetramethoxystilbene (134029-62-2)

Guidance literature:

With dodecacarbonyl-triangulo-triruthenium; water; N,N-dimethyl-formamide; triphenylphosphine; trifluoroacetic acid; at 145 ℃; for 3h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201003662

upstream raw materials:

triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide

4-methoxy-benzaldehyde

(3,4,5-trimethoxybenzyl)diphenylphosphine oxide

2-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethan-1-ol

Downstream raw materials:

1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane

(1S,2S)-1-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-ethane-1,2-diol

(1R,2R)-1-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-ethane-1,2-diol

3,5,4'-trimethoxy-trans-stilbene

Refernces

A Ramberg-Baecklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212

10.1039/b702411h

The study presents a concise synthetic route to the anti-cancer agents combretastatin A-4 and DMU-212 using the Ramberg–B?cklund reaction. Combretastatin A-4, isolated from the African tree Combretum caffrum, is a potent inhibitor of tubulin polymerization, while DMU-212 is a synthetic analogue with cancer chemoprotective activity. The synthesis of combretastatin A-4 begins with the coupling of thiol 13, prepared from 3,4,5-trimethoxybenzyl alcohol using Lawesson’s reagent, and bromide 14, using potassium hydroxide in ethanol. The resulting sulfide is oxidized with m-chloroperoxybenzoic acid to form sulfone 12. The Ramberg–B?cklund reaction, carried out under various conditions (Meyers, Chan, and Franck), converts sulfone 12 into the stilbene intermediate 15, which is then desilylated to yield combretastatin A-4. The study also explores the synthesis of other combretastatin analogues, including (E)- and (Z)-2012, using similar procedures. The Ramberg–B?cklund reaction is further applied to prepare DMU-212 from sulfone 29, derived from 4-methoxybenzyl mercaptan and bromide 17. The study highlights the efficiency and stereoselectivity of the Ramberg–B?cklund reaction in synthesizing these anti-cancer stilbenes and provides insights into the reaction's scope and limitations.

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