22411-59-2

Usage

InChI:InChI=1/C13H17NO/c1-3-14(4-2)13-9-7-12(8-10-13)6-5-11-15/h5-11H,3-4H2,1-2H3/b6-5+

Upstream product

• 120-21-8 4-Diethylaminobenzaldehyde 
• 20883-91-4 p-Diaethylamino-zimtsaeure-methylester 
• 119516-31-3 [4-((E)-2-[1,3]Dioxolan-2-yl-vinyl)-phenyl]-diethyl-amine 
• 119516-35-7 (E)-3-(4-(diethylamino)phenyl)acrylonitrile 
• 91-66-7 N,N-diethylaniline 
• 927-63-9 3-dimethylaminoacrolein 
• 75-07-0 acetaldehyde 
• 119539-85-4 trans-4-diethylaminocinnamyl alcohol 
• 23521-49-5 (Z)-1-bromo-2-ethoxyethene 
• 113832-57-8 N-ethylidenecyclohexylamine 

Downstream Products

• 51325-83-8 2-benzoyl-5-(4-diethylamino-phenyl)-penta-2,4-dienenitrile 
• 253345-06-1 N,N-diethyl-4-[(1E,3E)-4-(2,2'-bithien-5-yl)-1,3-butadienyl]aniline 
• 1427057-64-4 (3E,5E)-3,5-bis{(2E)-3-[4-(diethylamino)phenyl]prop-2-en-1-ylidene}piperidin-4-one 
• 1427057-62-2 (3E,5E)-3,5-bis{(2E)-3-[4-(diethylamino)phenyl]prop-2-en-1-ylidene}-1-ethylpiperidin-4-one 
• 1333480-85-5 (5Z)-5-((2E)-3-[4-(diethylamino)phenyl]prop-2-en-1-ylidene)imidazolidine-2,4-dione 
• 1292323-62-6 (E)-tert-butyl 2-(3-(4-(diethylamino)phenyl)allylamino)ethylcarbamate 

Relevant academic research and scientific papers

Aromatic amines in organic synthesis. Part ii. p‐aminocinnamaldehydes

Ten derivatives of p‐aminocinnamic aldehydes were prepared from the reaction of either aromatic amines with dimethylaminoacrolein or benzaldehydes with acetaldehyde. Their chemical structure and purity were verified by1H NMR,13C NMR and IR spectroscopic methods. We found that the synthesis applying dimethylaminoacrolein as the reagent gets better yields than the one based on the reaction with acetaldehyde. The yields of the cinnamic aldehydes varied according to the type of the amino group and the number and position of the substituents. The basic spectroscopic properties of the p‐aminocinnamic aldehydes are also described since the compounds may be a precursor for the synthesis of dyes for diverse applications, e.g., in medicine and optoelectronics.

Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.

Synthesis of 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole derivatives and their effects on neuronal cell death

Novel 3-[4-(dimethylamino)phenyl]alkyl-2-oxindole analogs were synthesized by either of the following two pathways: (1) a sequence of Knoevenagel condensation of oxindole with (4-dimethylamino)cinnamaldehyde–hydrogenation, or (2) alkylation of oxindole dianion with [(4-dimethylamino)phenyl]alkyl halides. Subsequent alkylation at C-3 and/or N-1 of the oxindole skeleton by anion-based methods provided additional substituted derivatives for structure-activity relationship studies. Their effects on neuronal cell death induced by oxidative stress were evaluated by lactate dehydrogenase assay. Compounds with the alkyl chain length of 2–4 significantly suppressed the neuronal cell death. No significant change occurred in the activity by substitution with less-polar groups. The stereochemistry at C-3 of the oxindole core was also irrelevant for the neuroprotective effects of these compounds.

Emission wavelength prediction of a full-color-tunable fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

Analogs of Michler's ketone for two-photon absorption initiation of polymerization in the near infrared: Synthesis and photophysical properties

We present the synthesis of substituted ketones, conjugated analogs of Michler's ketone. These molecules exhibit broadband TPA properties between 700 and 1100 nm due to a charge transfer from the terminal amino groups to the central ketone function and wi

IMPROVED SYNTHESIS OF TRANS-4-DIETHYLAMINOCINNAMALDEHYDE

The title compound was prepared from diisobutylaluminum hydride reduction of 4-diethylaminocinnamonitrile, which in turn was obtained by condensing 4-diethylaminobenzaldehyde and cyanoacetic acid.