cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne

Base Information

• Chemical Name: cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne
• CAS No.: 868542-79-4
• Molecular Formula: C₂₀H₁₃NO₆S₂
• Molecular Weight: 427.458
• Mol file: 868542-79-4.mol

Synonyms:cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne

Chemical Property of cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne

There total 2 articles about cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne 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: 39.0%

3-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-(trimethylsilyl)propyne (396720-96-0) + 1,1-dibromo-4-(4-nitrophenyl)but-1-en-3-yne (839673-71-1) → cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne (868542-79-4)

Guidance literature:

1,1-dibromo-4-(4-nitrophenyl)but-1-en-3-yne; With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 20 ℃; for 1h;

3-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-(trimethylsilyl)propyne; With diisopropylamine; In tetrahydrofuran; toluene;

DOI:10.1002/ejoc.200500287

Reference yield:

3-(4-nitrophenyl)prop-2-ynal (35487-34-4) → cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne (868542-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 72 percent / Zn; PPh₃ / CH₂Cl₂ / 0.75 h

2.1: Bu₃SnH / Pd(PPh₃)4 / toluene / 1 h / 20 °C

2.2: 39 percent / HN(iPr)2 / toluene; tetrahydrofuran

With tri-n-butyl-tin hydride; triphenylphosphine; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; toluene; 1.1: Corey-Fuchs dibromoolefination;

DOI:10.1002/ejoc.200500287

Reference yield: 100.0%

cis-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne (868542-79-4) → trans-7-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-[4-nitrophenyl]hept-3-en-1,5-diyne

Guidance literature:

at 50 ℃; for 6h; Product distribution;

DOI:10.1002/ejoc.200500287

upstream raw materials:

3-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-1-(trimethylsilyl)propyne

1,1-dibromo-4-(4-nitrophenyl)but-1-en-3-yne

3-(4-nitrophenyl)prop-2-ynal