Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-

Base Information

• Chemical Name: Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-
• CAS No.: 81764-99-0
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.236
• Mol file: 81764-99-0.mol

Synonyms:

Chemical Property of Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-

There total 1 articles about Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)- 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: 96.0%

4-cyanobenzaldehyde (105-07-7) + acetylacetone (123-54-6,81235-32-7) → 4'-cyano-3-benzylidene-2,4-pentanedione (81764-99-0)

Guidance literature:

With L-Tryptophan; In dimethyl sulfoxide; at 20 ℃; for 24h;

DOI:10.1016/j.catcom.2010.01.016

Reference yield: 82.0%

1-methyl-4-((2-phenylallyl)sulfonyl)benzene (16212-08-1,54897-33-5,20605-47-4) + 4'-cyano-3-benzylidene-2,4-pentanedione (81764-99-0) → 4-((2R*,6R*)-3-acetyl-4-hydroxy-6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridin-2-yl)benzonitrile

Guidance literature:

4'-cyano-3-benzylidene-2,4-pentanedione; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at 0 ℃; for 0.666667h; Inert atmosphere;

1-methyl-4-((2-phenylallyl)sulfonyl)benzene; In tetrahydrofuran; at -50 ℃; for 4h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2021.132285

Reference yield: 78.0%

(2-nitroethenyl)benzene (102-96-5) + 4'-cyano-3-benzylidene-2,4-pentanedione (81764-99-0) → 4-(2-acetyl-3-hydroxy-6-nitro-5-phenylcyclohex-2-enyl)benzonitrile

Guidance literature:

4'-cyano-3-benzylidene-2,4-pentanedione; With lithium diisopropyl amide; In tetrahydrofuran; at -50 ℃; for 0.75h; Inert atmosphere;

(2-nitroethenyl)benzene; In tetrahydrofuran; at -50 ℃; for 4h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.5b01768

upstream raw materials:

4-cyanobenzaldehyde

acetylacetone

Downstream raw materials:

4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)benzonitrile

(rac)-4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile

(rac)-4-(6-Acetyl-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile

Refernces

• 1、 Ding, Yan,Ni, Xiao,Gu, Mengjie,Li, Shuang,Huang, He,Hu, Yi. "Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalyzed by lipoprotein lipase". . p. 101 - 104. Retrieved 2015/02/19.
• 2、 Hu, Ying,He, Yan-Hong,Guan, Zhi. "A simple method for the preparation of functionalized trisubstituted alkenes and α,β,γ,δ-unsaturated carbonyl compounds by using natural amino acid l-tryptophan". scheme or table. p. 656 - 659. Retrieved 2010/11/05.