7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trienal

Base Information

• Chemical Name: 7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trienal
• CAS No.: 55298-77-6
• Molecular Formula: C15H17NO
• Molecular Weight: 227.306
• DSSTox Substance ID: DTXSID00709667
• Mol file: 55298-77-6.mol

Synonyms:SCHEMBL8722663;DTXSID00709667;7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trienal

Chemical Property of 7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trienal

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 227.131014166
• Heavy Atom Count: 17
• Complexity: 294

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=CC=CC=CC=O

Technology Process of 7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trienal

There total 6 articles about 7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trienal 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: 65.0%

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide (52509-14-5) + s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal (20432-36-4) → (2E,4E,6E)-7-(4-(dimethylamino)phenyl)hepta-2,4,6-trienal (55298-77-6)

Guidance literature:

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal; With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1081/SCC-120015766

Reference yield:

3-(4-dimethylamino-phenyl)-propenal (20432-35-3,6203-18-5) → (2E,4E,6E)-7-(4-(dimethylamino)phenyl)hepta-2,4,6-trienal (55298-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 18-crown-6; NaH / tetrahydrofuran / 20 °C

1.2: 92 percent / 20 percent HCl / tetrahydrofuran / 2 h / 20 °C

2.1: 18-crown-6; NaH / tetrahydrofuran / 20 °C

2.2: 65 percent / 20 percent HCl / tetrahydrofuran / 2 h / 20 °C

With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; 1.1: Wittig reaction / 2.1: Wittig reaction;

DOI:10.1081/SCC-120015766

Reference yield:

C17H21NO2 → (2E,4E,6E)-7-(4-(dimethylamino)phenyl)hepta-2,4,6-trienal (55298-77-6)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.5h;

DOI:10.1021/acs.analchem.7b02246

upstream raw materials:

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal

3-(4-dimethylamino-phenyl)-propenal

4-dimethylamino-benzaldehyde

Refernces

• 1、 Gustav, Klaus,Bartsch, Ulrich. "Spectroscopic Studies on Organic Carbonyl Compounds, IX: On Synthesis and Spectroscopy of 1-Phenyl-11-(4-dimethyl-amino-phenyl)-undeca-4,6,8,10-tetraene-1,3-dione". . p. 43 - 46. Retrieved 1994.
• 2、 Zhou, Kaixiang,Fu, Hualong,Feng, Liang,Cui, Mengchao,Dai, Jiapei,Liu, Boli. "The synthesis and evaluation of near-infrared probes with barbituric acid acceptors for in vivo detection of amyloid plaques". supporting information. p. 11665 - 11668. Retrieved 2015/07/15.