dimethyl 2-[(E)-7-(2-bromophenyl)hept-4-enyl]propanedioate

Base Information

• Chemical Name: dimethyl 2-[(E)-7-(2-bromophenyl)hept-4-enyl]propanedioate
• CAS No.: 188004-28-6
• Molecular Formula: C18H23BrO4
• Molecular Weight: 383.282
• DSSTox Substance ID: DTXSID201166613
• Nikkaji Number: J1.992.357F
• Mol file: 188004-28-6.mol

Synonyms:DTXSID201166613;188004-28-6;1,3-Dimethyl 2-[(4E)-7-(2-bromophenyl)-4-hepten-1-yl]propanedioate

Chemical Property of dimethyl 2-[(E)-7-(2-bromophenyl)hept-4-enyl]propanedioate

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 382.07797
• Heavy Atom Count: 23
• Complexity: 379

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CCCC=CCCC1=CC=CC=C1Br)C(=O)OC
• Isomeric SMILES: COC(=O)C(CCC/C=C/CCC1=CC=CC=C1Br)C(=O)OC

Technology Process of dimethyl 2-[(E)-7-(2-bromophenyl)hept-4-enyl]propanedioate

There total 8 articles about dimethyl 2-[(E)-7-(2-bromophenyl)hept-4-enyl]propanedioate 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: 80.0%

malonic acid dimethyl ester (108-59-8) + 1-Bromo-2-((E)-7-iodo-hept-3-enyl)-benzene (710980-24-8) → (E)-2-[7-(2-bromophenyl)hept-4-enyl]malonic acid dimethyl ester (188004-28-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/j.tet.2004.03.023

Reference yield:

malonic acid dimethyl ester (108-59-8) + Methanesulfonic acid (E)-7-(2-bromo-phenyl)-hept-4-enyl ester → (E)-2-[7-(2-bromophenyl)hept-4-enyl]malonic acid dimethyl ester (188004-28-6)

Guidance literature:

With sodium hydride; potassium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/S0040-4039(96)02442-2

Reference yield:

1-Bromo-2-iodobenzene (583-55-1) → (E)-2-[7-(2-bromophenyl)hept-4-enyl]malonic acid dimethyl ester (188004-28-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 76 percent / NaHCO₃; triethylbenzylammonium chloride / Pd(OAc)2 / dimethylformamide / 24 h / 50 °C

2: 90 percent / tetrahydrofuran / -30 - 20 °C

3: 80 percent / propionic acid / 15 h / Heating

4: 76 percent / LiAlH₄ / diethyl ether / 1 h / 20 °C

5: triethylamine / CH₂Cl₂ / 5 h / 0 - 20 °C

6: 2.6 g / sodium iodide / acetone / 12 h / Heating

7: 80 percent / NaH / various solvent(s); tetrahydrofuran; dimethylformamide / 70 °C

With lithium aluminium tetrahydride; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; sodium hydrogencarbonate; propionic acid; triethylamine; sodium iodide; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; 3: Claisen rearrangement;

DOI:10.1016/j.tet.2004.03.023

upstream raw materials:

malonic acid dimethyl ester

1-Bromo-2-((E)-7-iodo-hept-3-enyl)-benzene

1-Bromo-2-iodobenzene

3-(o-bromophenyl)propanal