(E)-N,N-dibutyl-3-phenylprop-2-enamide

Base Information

• Chemical Name: (E)-N,N-dibutyl-3-phenylprop-2-enamide
• CAS No.: 23784-57-8
• Molecular Formula: C17H25NO
• Molecular Weight: 259.392
• NSC Number: 6057
• DSSTox Substance ID: DTXSID60417776
• Wikidata: Q82227944
• Mol file: 23784-57-8.mol

Synonyms:NSC6057;23784-57-8;DTXSID60417776;NSC-6057;AKOS003850450

Chemical Property of (E)-N,N-dibutyl-3-phenylprop-2-enamide

Chemical Property:

• Vapor Pressure: 4.8E-07mmHg at 25°C
• Boiling Point: 413.4°C at 760 mmHg
• Flash Point: 184.5°C
• Density: 0.972g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 259.193614421
• Heavy Atom Count: 19
• Complexity: 258

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN(CCCC)C(=O)C=CC1=CC=CC=C1
• Isomeric SMILES: CCCCN(CCCC)C(=O)/C=C/C1=CC=CC=C1

Technology Process of (E)-N,N-dibutyl-3-phenylprop-2-enamide

There total 10 articles about (E)-N,N-dibutyl-3-phenylprop-2-enamide 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%

N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) + N,N-Dibutyl-2-(triphenyl-λ5-phosphanylidene)-acetamide (78074-90-5) → dibutylamide of cinnamic acid (23784-57-8)

Guidance literature:

In dimethyl sulfoxide; at 100 ℃; for 12h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201001379

Reference yield: 64.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + tributyl-amine (102-82-9) + carbon monoxide (201230-82-2) → dibutylamide of cinnamic acid (23784-57-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; oxygen; copper(II) acetate monohydrate; In dimethyl sulfoxide; toluene; at 110 ℃; for 24h; chemoselective reaction; Schlenk technique;

DOI:10.1039/c4cc08925a

Reference yield: 58.0%

tetrabutylthiuram Disulfide (1634-02-2) + (E)-3-phenylacrylic acid (140-10-3) → dibutylamide of cinnamic acid (23784-57-8)

Guidance literature:

In 1,2-dichloro-ethane; at 100 ℃; for 48h; Sealed tube;

DOI:10.1002/ejoc.201901630

upstream raw materials:

cinnamoyl chloride

dibutylamine

benzaldehyde

oxide of diphenylphosphite

Refernces

• 1、 Fokoue,Marques,Correia,Yamaguchi,Qu,Aires-De-Sousa,Scotti,Lopes,Kato. "Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data". . p. 21407 - 21413. Retrieved 2018/06/26.
• 2、 Fang, Fan,Li, Yuan,Tian, Shi-Kai. "Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes". experimental part. p. 1084 - 1091. Retrieved 2011/04/15.