3-OXO-5-PHENYL-4-PENTENENITRILE

Base Information

• Chemical Name: 3-OXO-5-PHENYL-4-PENTENENITRILE
• CAS No.: 6704-83-2
• Molecular Formula: C11H9NO
• Molecular Weight: 171.199
• Hs Code.: 2926909090
• Mol file: 6704-83-2.mol

Synonyms:3-OXO-5-PHENYL-4-PENTENENITRILE;4-CYANO-1-PHENYLBUT-1-EN-3-ONE

Chemical Property of 3-OXO-5-PHENYL-4-PENTENENITRILE

Chemical Property:

• PSA: 40.86000
• LogP: 2.18258

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-OXO-5-PHENYL-4-PENTENENITRILE

There total 5 articles about 3-OXO-5-PHENYL-4-PENTENENITRILE 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: 64.0%

acetonitrile (75-05-8,26809-02-9) + methyl cinnamate (103-26-4,1754-62-7) → 3-oxo-5-phenyl-4-pentenonitrile (6704-83-2)

Guidance literature:

With potassium tert-butylate; isopropyl alcohol; In 2-methyltetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.3762/bjoc.15.287

Reference yield: 50.0%

trimethylsilyl cyanide (7677-24-9) + trimethylsilyl(4-phenylbuta-1,3-dien-2-yloxy)silane (61140-47-4,124306-12-3,73400-25-6) → 3-oxo-5-phenyl-4-pentenonitrile (6704-83-2)

Guidance literature:

With iodosylbenzene; boron trifluoride diethyl etherate; In acetonitrile; at -30 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01102

Reference yield:

1-Phenylbut-1-en-3-one (122-57-6) → 3-oxo-5-phenyl-4-pentenonitrile (6704-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium iodide; triethylamine / acetonitrile / 40 °C / Inert atmosphere

2: boron trifluoride diethyl etherate; iodosylbenzene / acetonitrile / 3 h / -30 °C / Inert atmosphere

With iodosylbenzene; boron trifluoride diethyl etherate; triethylamine; sodium iodide; In acetonitrile;

DOI:10.1021/acs.joc.5b01102

upstream raw materials:

cinnamoyl chloride

cyanoacetic acid

trimethylsilyl cyanide

trimethylsilyl(4-phenylbuta-1,3-dien-2-yloxy)silane

Downstream raw materials:

2-Amino-4-phenyl-6-((E)-styryl)-4H-pyran-3,5-dicarbonitrile

(Z)-2-Cyano-2-(4-oxo-2-phenyl-2-pyrrolin-5-yliden)essigsaeureethylester

(E)-3-Oxo-5-phenyl-2-[1-phenyl-meth-(E)-ylidene]-pent-4-enenitrile

4-Hydroxy-2,6-diphenyl-1-[(Z)-(3-phenyl-acryloyl)]-cyclohex-3-ene-1,3-dicarbonitrile

Refernces

• 1、 Shen, Hang,Li, Jiaqiang,Liu, Qing,Pan, Jing,Huang, Ruofeng,Xiong, Yan. "Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers". . p. 7212 - 7218. Retrieved 2015/07/28.