24954-67-4Relevant articles and documents
A convenient synthesis of 4-nitrophenethylamine hydrochloride
Joshi, Uday M.,Kobal, Balu S.,Joshi, Hemant V.
, p. 1829 - 1832 (2003)
A short, convenient, and efficient synthesis of 4-nitrophenethylamine hydrochloride is described. The key step involved removal of water from 4-nitrophenylalanine monohydrate followed by decarboxylation.
A process for preparing a broad pH fluorescent probe of the organic compound and use thereof (by machine translation)
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Paragraph 0081; 0082; 0083, (2018/04/03)
The present invention discloses a process for the preparation of a wide range of fluorescent probe in the pH of the organic compound, the organic compound can be produced according to the actual need to carry out any proportion of combination, and can be fixed in the hydrophilic high polymer further preparing and detecting water environment acidity and alkalinity of the product. The product can be realized to the pH value of the continuous measuring, thereby greatly improving the efficiency, sensitivity and repeatability. (by machine translation)
Organic compound for detecting content of metal ions in water and application of organic compound
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Paragraph 0027, (2018/09/14)
The invention discloses an organic compound for detecting the content of metal ions. The compound adopts N-carbethoxy-N-methylpyridaniline as a metal ion complexing body, chromophore or fluorophore isintroduced into a molecule to generate a developing ind
Protonation switching to the least-basic heteroatom of carbamate through cationic hydrogen bonding promotes the formation of isocyanate cations
Kurouchi, Hiroaki,Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
supporting information, p. 8682 - 8690 (2014/07/21)
We found that phenethylcarbamates that bear ortho-salicylate as an ether group (carbamoyl salicylates) dramatically accelerate O-C bond dissociation in strong acid to facilitate generation of isocyanate cation (N-protonated isocyanates), which undergo subsequent intramolecular aromatic electrophilic cyclization to give dihydroisoquinolones. To generate isocyanate cations from carbamates in acidic media as electrophiles for aromatic substitution, protonation at the ether oxygen, the least basic heteroatom, is essential to promote C-O bond cleavage. However, the carbonyl oxygen of carbamates, the most basic site, is protonated exclusively in strong acids. We found that the protonation site can be shifted to an alternative basic atom by linking methyl salicylate to the ether oxygen of carbamate. The methyl ester oxygen ortho to the phenolic (ether) oxygen of salicylate is as basic as the carbamate carbonyl oxygen, and we found that monoprotonation at the methyl ester oxygen in strong acid resulted in the formation of an intramolecular cationic hydrogen bond (>C=O+-H...O) with the phenolic ether oxygen. This facilitates O-C bond dissociation of phenethylcarbamates, thereby promoting isocyanate cation formation. In contrast, superacid-mediated diprotonation at the methyl ester oxygen of the salicylate and the carbonyl oxygen of the carbamate afforded a rather stable dication, which did not readily undergo C-O bond dissociation. This is an unprecedented and unknown case in which the monocation has greater reactivity than the dication.
4-Amino-1,8-naphthalimide-based fluorescent sensor with high selectivity and sensitivity for Zn2 + imaging in living cells
Liu, Da-Ying,Qi, Jing,Liu, Xiao-Yan,He, Hua-Rui,Chen, Jia-Tong,Yang, Guang-Ming
, p. 173 - 178 (2014/04/03)
A new 4-amino-1,8-naphthalimide-based fluorescent sensor with iminodiacetic acid as receptor, was synthesized and characterized. Under physiological pH conditions, it demonstrates high selectivity and sensitivity for sensing Zn 2 + with about 5
Activation of electrophilicity of stable Y-delocalized carbamate cations in intramolecular aromatic substitution reaction: Evidence for formation of diprotonated carbamates leading to generation of isocyanates
Kurouchi, Hiroaki,Kawamoto, Kyoko,Sugimoto, Hiromichi,Nakamura, Satoshi,Otani, Yuko,Ohwada, Tomohiko
, p. 9313 - 9328,16 (2012/12/11)
Although cations with three heteroatoms, such as monoprotonated guanidine and urea, are stabilized by Y-shaped conjugation and such Y-conjugated cations are sufficiently basic to be further protonated (or protosolvated) to dications in strongly acid media, only O-monoprotonated species have been detected in the case of carbamates even in magic acid. We found that the trifluoromethanesulfonic acid-catalyzed cyclization of arylethylcarbamates proceeds to afford dihydroisoquinolones in high yield. In strong acids, methyl carbamates are fully O-monoprotonated, and these monocations do not undergo cyclization even under heating. But, as the acidity of the reaction medium is further increased, the cyclization reaction of methyl phenethylcarbamates starts to proceed as a first-order reaction, with a linear relationship between rate and acidity. The sign and magnitude of the entropy of activation ΔS ? were found to be similar to those of other AAc1 reactions. These results strongly support the idea that further protonation of the O-protonated carbamates is involved in the cyclization, but the concentration of the dications is very low and suggests that the rate-determining step is dissociation of methanol from the diprotonated carbamate to generate protonated isocyanate, which reacts with the aromatic ring. Therefore, O-protonated carbamates are weak bases in sharp contrast to other Y-shaped monocations.
Improved protocol for indoline synthesis via palladium-catalyzed intramolecular C(sp2)-H amination
He, Gang,Lu, Chengxi,Zhao, Yingsheng,Nack, William A.,Chen, Gong
supporting information; experimental part, p. 2944 - 2947 (2012/08/28)
An efficient method has been developed for the synthesis of indoline compounds from picolinamide (PA)-protected β-arylethylamine substrates via palladium-catalyzed intramolecular amination of ortho-C(sp2)-H bonds. These reactions feature high efficiency, low catalyst loadings, mild operating conditions, and the use of inexpensive reagents.
Synthesis and evaluation of novel phenylethanolamine derivatives containing acetanilides as potent and selective b 3-adrenergic receptor agonists
Maruyama, Tatsuya,Onda, Kenichi,Hayakawa, Masahiko,Suzuki, Takayuki,Kimizuka, Tetsuya,Matsui, Tetsuo,Takasu, Toshiyuki,Nagase, Itsuro,Hamada, Noritaka,Ohta, Mitsuaki
experimental part, p. 533 - 545 (2010/09/06)
In the search for potent and selective human β3-adrenergic receptor (AR) agonists as potential pharmacotherapies for the treatment of obesity and non-insulin dependent (type II) diabetes, we prepared a novel series of phenylethanolamine derivatives containing acetanilides and evaluated their biological activities at the human β3-, β2-, and β1-ARs. Among these compounds, the 6-amino-2-pyridylacetanilide (36b), 2-amino-5- methylthiazol- 4-ylacetanilide (36g), and 5-amino-1,2,4-thiadiazol-3- ylacetanilide (36h) derivatives showed potent agonistic activity at the β3-AR with functional selectivity over the β1- and β2-ARs. In addition, these compounds exhibited significant hypoglycemic activity in a rodent diabetic model.
Efficient transformation of azides to primary amines using the mild and easily accessible CeCl3·;7H2O/NaI system
Bartoli, Giuseppe,Di Antonio, Giustino,Giovannini, Riccardo,Giuli, Sandra,Lanari, Silvia,Paoletti, Melissa,Marcantoni, Enrico
, p. 1919 - 1924 (2008/09/18)
(Chemical Equation Presented) Because of the nitrogen functionality, the azido group plays an important role in the synthesis of amines, and numerous reduction methods of azides to primary amines are reported. Recent reports have highlighted the capability of NaI as a useful reagent for this transformation when it is used in combination with a Lewis acid promoter. However, these methods often suffer from harsh reaction conditions; for this reason, the development of a simple and efficient protocol using NaI in presence of inexpensive and readily available cerium salts Lewis acids would extend the scope of this organic transformation. In continuation of our interest on the use of the CeCl3·7H2O/NaI system, in this paper we report how azides undergo reduction by NaI in the presence of CeCl 3·7H2O in refluxing acetonitrile under neutral conditions to produce the corresponding primary amines. The rate and yield of the reaction are considerably improved by employing this microwave-assisted procedure, and this may be of value for the preparation of densely functionalized molecules having biological and pharmaceutical activities.
The facile preparation of primary and secondary amines via an improved Fukuyama-Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent
Guisado, Cristina,Waterhouse, Jodie E.,Price, Wayne S.,Jorgensen, Michael R.,Miller, Andrew D.
, p. 1049 - 1057 (2007/10/03)
An efficient modification of the Fukuyama-Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reagents, generates reaction by-products that can be easily removed, providing a remarkably clean product mixture. This improved technique was implemented in the synthesis of a complex lipopeptide designed to target α 9β1-integrin proteins predominant on upper airway epithelial cells. The Royal Society of Chemistry 2005.
