3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione

Base Information

• Chemical Name: 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione
• CAS No.: 507485-39-4
• Molecular Formula: C₂₀H₂₀N₄O₂
• Molecular Weight: 348.404
• Mol file: 507485-39-4.mol

Synonyms:3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione

Chemical Property of 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione

There total 13 articles about 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione 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:

1-acetyl-3-{(Z)-1-[5-(1,1-dimethyl-2-propenyl)-1H-4-imidazolyl]methylidene}-2,5-piperazinedione (714273-82-2) + benzaldehyde (100-52-7) → 3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione (351325-37-6) + 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione (507485-39-4)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; for 5h; Heating / reflux;

Reference yield:

(+/-)-Phenylahistin → 3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione (351325-37-6) + 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione (507485-39-4)

Guidance literature:

With cell-free extract of Streptomyces albulus KO-23; In dimethyl sulfoxide; at 50 ℃; for 24h; pH=8.0; Enzymatic reaction;

DOI:10.7164/antibiotics.55.1042

Reference yield:

2,2-dimethyl-3-(toluene-4-sulfonyloxy)-butyric acid methyl ester (714273-85-5) → 3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione (351325-37-6) + 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione (507485-39-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3.5 h / 140 - 160 °C

2.1: sodium hydroxide; water / ethanol

3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 17 h / 0 - 20 °C

4.1: [2,2]bipyridinyl; n-butyllithium / tetrahydrofuran; hexane / -70 - -10 °C

4.2: 3 h / -60 - 0 °C

5.1: sulfuryl dichloride / chloroform / 2.5 h / 0 - 20 °C / Heating / reflux

6.1: water / 5 h / 150 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C

7.2: 0.17 h

8.1: manganese(IV) oxide / acetone / 5 h / 20 °C

9.1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 20 - 45 °C

10.1: caesium carbonate / N,N-dimethyl-formamide / 5 h / Heating / reflux

With [2,2]bipyridinyl; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; sulfuryl dichloride; oxalyl dichloride; water; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione

1-acetyl-3-{(Z)-1-[5-(1,1-dimethyl-2-propenyl)-1H-4-imidazolyl]methylidene}-2,5-piperazinedione

benzaldehyde

2,2-dimethyl-3-(toluene-4-sulfonyloxy)-butyric acid methyl ester

Downstream raw materials:

3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione

Refernces

• 1、 -. "ANALOGS OF DEHYDROPHENYLAHISTINS AND THEIR THEAPEUTIC USE". Page/Page column 25-26. . Retrieved 2008/12/08.