82222-45-5

Upstream product

• 117998-09-1 α-(hydroxymethylene)-4-nitrophenylacetonitrile 
• 91-68-9 3-diethylaminophenol 
• 64-67-5 diethyl sulfate 
• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 555-21-5 4-Nitrophenylacetonitrile 
• 140-29-4 phenylacetonitrile 
• 104-03-0 4-nitrobenzeneacetic acid 
• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 23764-68-3 5-Diethylamino-2-{[(E)-4-nitro-phenylimino]-methyl}-phenol 
• 82222-37-5 (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol 

Relevant academic research and scientific papers

Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties

High level time-dependent density functional theory (TD-DFT) computational modeling of coumarin dyes has been exploited for guiding the design of effective photocatalysts (PCs). A library of coumarins were investigated from the theoretical point of view and photophysical/electrochemical properties (absorption and emission spectra, E00, oxidation and reduction potentials) were evaluated. Comparison with literature values reported for a few candidates has been used for assessing the level of theory. On the basis of the results obtained, new strongly reducing PCs [Eox(PC.+/PC*)=?2.1 – ?2.0 V vs SCE] were discovered. Through the computational study of structure-properties relationships, a number of coumarins derivatives have been synthesized and evaluated in the pinacol coupling of aldehydes as the model reaction. The new organic photoredox catalysts show experimental photophysical and electrochemical data in accordance with the ones predicted by calculation, with excited state reduction potentials surpassing those of highly reducing transition metal-based PCs. A careful investigation of their behavior as PC has revealed crucial issues that need to be taken into consideration in the general photoredox catalysis, shedding light on the use of these PC in the pinacol, as well as, in other photoredox reactions.

MANUFACTURING METHOD OF COUMARIN DERIVATIVE, MANUFACTURING METHOD OF FLUORESCENT AGENT FOR COLORING AND MANUFACTURING METHOD OF DYE FOR FLUORESCENCE

PROBLEM TO BE SOLVED: To provide an easier, low cost and high yield manufacturing method of 3-aryl-7-N,N-dialkyl aminocoumarin derivative. SOLUTION: There is provided a manufacturing method of 3-aryl-7-dialkyl aminocoumarin derivative represented by the formula (3) by reacting acrylic acids having a 4-amino-2-carboxy-phenyl group and further a phenyl group, dialkyl sulfate compound, Lewis acid at same time or in sequence in a same bath. (3), where Ar is a phenyl group, a thienyl group, a pyridyl group or a naphthyl group which may have a substituent, R3 is a C1 to 4 linear/branched alkyl group, R4 is H, C1 to 8 linear/branched alkyl group, benzyl group or the like. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Selective selenol fluorescent probes: Design, synthesis, structural determinants, and biological applications

Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo.

Efficient synthesis of 3-substituted coumarins

The Mukaiyama's esterification protocol, using 2-chloro-1-methylpyridinium iodide-triethylamine reagent, has been successfully exploited to provide rapid access to a variety of 3-substituted coumarins in satisfactory yields.

Coumarins: Fast Synthesis by Knoevenagel Condensation under Microwave Irradiation

Condensation of salicyaldehyde or its derivatives with various derivatives of ethyl acetate in the presence of piperidine leads to the synthesis of coumarins by a solvent free reaction under microwave irradiation.

Coumarin derivatives, process for their preparation, their use and thiazolyl acetic acid derivatives as intermediates

Coumarin deviatives of the formula STR1 in which R1 denotes cyano, R2 represents phenyl or thiazolyl bonded in the 2-, 4-, or 5-position, R3 denotes hydrogen, C1 -C4 -alkyl or C1 -C4 -alkoxycarbonyl-C1 -C4 -alkyl and R4 represents hydrogen, C1 -C4 -alkyl or phenylsulphonyl, where C1 -C4 -alkyl can be substituted by hydroxyl, amino, carboxyl or C1 -C4 -alkoxy-carbonyl and phenyl can be monosubstituted or disubstituted by chlorine, bromine or C1 -C4 -alkyl, where furthermore R3 and R4, together with the N atom which they substitute, can denote a morpholine ring, a piperazine ring or a triazole ring which can carry one or two substituents from the group comprising methyl, ethyl and phenyl, and where furthermore one of the radicals R2, R3 and R4 denotes or carries a primary or secondary amino group, the hydroxyl group, the carboxyl group or the C1 -C4 -alkoxy-carbonyl group or can be converted into such a group by hydrolysis or hydrogenation, are suitable for dyeing biologically active compounds.

A Simple Route to N(2'-Hydroxy)-arylidene-nitroanilines-Versatile Synthones for Coumarines

In a three-component reaction with ortho formic esters and nitroaniline activated phenols are easily transferred to N(2'-hydroxy)-arylidene-nitroanilines.The reaction is commonly applicable and gives the N(2'-hydroxy-4'-N,N-dialkylamino)-benzylidene-nitroanilines 10 in good yields also with the air-unstable m-N,N-dialkylaminophenols 8.The prepared 2-hydroxy-azomethines are convertable into boroncomplexes 14 and coumarine derivatives 17, respectively.