5824-40-8Relevant academic research and scientific papers
A new polymorph of triphenyl-methyl-amine: The effect of hydrogen bonding
Khrustalev, Victor N.,Borisova, Irina V.,Zemlyansky, Nikolai N.,Antipin, M. Yu.
, p. o31-o34 (2009)
Crystallization of the hexane reaction mixture after treatment of LiGe(OCH2CH2NMe2)3 with PH3CN 3 gives rise to a new triclinic (space group P ) polymorph of triphenyl-methyl-amine, Cl9H17N, (I), cont
Copper catalyzed reduction of azides with diboron under mild conditions
Chen, Yang,Deng, Shengqi,Gao, Yihua,Liu, Liwen,Liu, Yu,Lu, Da,Wang, Qianwen,Zhang, Xiao
supporting information, (2020/02/27)
We report herein the first Cu catalyzed reduction of azides with B2pin2 (pin = pinacolato) as the reductant under very mild conditions. A series of primary amines and amides were obtained in moderate to excellent yields with high chemoselectivity and good functional group tolerance. This reaction can be performed with a cheap copper salt, a simple NHC ligand and a diboron reagent.
Synthetic method of 3-hydroxyazetidine hydrochloride
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Paragraph 0065-0069, (2020/11/05)
The invention discloses a synthetic method of 3-hydroxyazetidine hydrochloride, and belongs to the field of pharmacy. The synthetic method of the 3-hydroxyazetidine hydrochloride comprises the following steps: introducing hydrogen chloride gas into a solution formed by N-(triphenylmethyl)-3-hydroxyazetidine and a first organic solvent to carry out a reaction of removing triphenylchloromethane, andcarrying out solid-liquid separation to obtain the 3-hydroxyazetidine hydrochloride. The period for preparing the 3-hydroxyazetidine hydrochloride by utilizing the synthesis method is short, the safety is good, the use of toxic or expensive reagents is avoided, the reaction yield is high, the 3-hydroxyazetidine hydrochloride with high quality purity can be obtained, the operation is simple and convenient, and the method is suitable for large-scale industrial production.
Structure-based design, synthesis, and evaluation of the biological activity of novel phosphoroorganic small molecule IAP antagonists
?upicka-S?owik, Agnieszka,Psurski, Mateusz,Grzywa, Renata,Cuprych, Monika,Ciekot, Jaros?aw,Goldeman, Waldemar,Wojaczyńska, El?bieta,Wojaczyński, Jacek,Oleksyszyn, Józef,Sieńczyk, Marcin
, p. 1350 - 1364 (2020/04/24)
One of the strategies employed by novel anticancer therapies is to put the process of apoptosis back on track by blocking the interaction between inhibitor of apoptosis proteins (IAPs) and caspases. The activity of caspases is modulated by the caspases themselves in a caspase/procaspase proteolytic cascade and by their interaction with IAPs. Caspases can be released from the inhibitory influence of IAPs by proapoptotic proteins such as secondary mitochondrial activator of caspases (Smac) that share an IAP binding motif (IBM). The main purpose of the present study was the design and synthesis of phosphorus-based peptidyl antagonists of IAPs that mimic the endogenous Smac protein, which blocks the interaction between IAPs and caspases. Based on the structure of the IAP antagonist and recently reported thiadiazole derivatives, we designed and evaluated the biochemical properties of a series of phosphonic peptides bearing the N-Me-Ala-Val/Chg-Pro-OH motif (Chg: cyclohexylglycine). The ability of the obtained compounds to interact with the binding groove of the X-linked inhibitor of apoptosis protein baculovirus inhibitor of apoptosis protein repeat (XIAP BIR3) domain was examined by a fluorescence polarization assay, while their potential to induce autoubiquitination followed by proteasomal degradation of cellular IAP1 was examined using the MDA-MB-231 breast cancer cell line. The highest potency against BIR3 was observed among peptides containing C-terminal phosphonic phenylalanine analogs, which displayed nanomolar Ki values. Their antiproliferative potential as well as their proapoptotic action, manifested by an increase in caspase-3 activity, was examined using various cell lines.
Isoselective Lactide Ring Opening Polymerisation using [2]Rotaxane Catalysts
Lim, Jason Y. C.,Yuntawattana, Nattawut,Beer, Paul D.,Williams, Charlotte K.
supporting information, p. 6007 - 6011 (2019/04/03)
Polylactide (PLA) is a fully biodegradable and recyclable plastic, produced from a bio-derived monomer: it is a circular economy plastic. Its properties depend upon its stereochemistry and isotactic PLA shows superior thermal-mechanical performances. Here, a new means to control tacticity by exploiting rotaxane conformational dynamism is described. Dynamic achiral [2]rotaxanes can show high isoselectivity (Pi=0.8, 298 K) without requiring any chiral additives and enchain by a chain end control mechanism. The organocatalytic dynamic stereoselectivity is likely applicable to other small-molecule and polymerization catalyses.
Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions
Hoshino, Yujiro,Shimbo, Yuki,Ohtsuka, Naoya,Honda, Kiyoshi
supporting information, p. 710 - 712 (2015/01/30)
A mild self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields. This alternative to traditional Lossen rearrangement provides a simple and mild method for the synthesis of amines from free hydroxamic acids.
A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: Catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations
Bagchi, Vivek,Paraskevopoulou, Patrina,Das, Purak,Chi, Lingyu,Wang, Qiuwen,Choudhury, Amitava,Mathieson, Jennifer S.,Cronin, Leroy,Pardue, Daniel B.,Cundari, Thomas R.,Mitrikas, George,Sanakis, Yiannis,Stavropoulos, Pericles
supporting information, p. 11362 - 11381 (2014/09/17)
A CuI catalyst (1), supported by a framework of strongly basic guanidinato moieties, mediates nitrene-transfer from PhI=NR sources to a wide variety of aliphatic hydrocarbons (C-H amination or amidination in the presence of nitriles) and olefins (aziridination). Product profiles are consistent with a stepwise rather than concerted C-N bond formation. Mechanistic investigations with the aid of Hammett plots, kinetic isotope effects, labeled stereochemical probes, and radical traps and clocks allow us to conclude that carboradical intermediates play a major role and are generated by hydrogen-atom abstraction from substrate C-H bonds or initial nitrene-addition to one of the olefinic carbons. Subsequent processes include solvent-caged radical recombination to afford the major amination and aziridination products but also one-electron oxidation of diffusively free carboradicals to generate amidination products due to carbocation participation. Analyses of metal- and ligand-centered events by variable temperature electrospray mass spectrometry, cyclic voltammetry, and electron paramagnetic resonance spectroscopy, coupled with computational studies, indicate that an active, but still elusive, copper-nitrene (S = 1) intermediate initially abstracts a hydrogen atom from, or adds nitrene to, C-H and C=C bonds, respectively, followed by a spin flip and radical rebound to afford intra- and intermolecular C-N containing products.
Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride
Goldeman, Waldemar,Soroka, Miroslaw
experimental part, p. 360 - 369 (2011/02/27)
The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.
Rapid Ti(Oi-Pr)4 facilitated synthesis of α,α,α-trisubstituted primary amines by the addition of Grignard reagents to nitriles under microwave heating conditions
Wang, Ruifang,Gregg, Brian T.,Zhang, Wei,Golden, Kathryn C.,Quinn, John F.,Cui, Peng,Tymoshenko, Dmytro O.
experimental part, p. 7070 - 7073 (2010/03/01)
A series of carbinamines (α,α,α-trisubstituted amines) have been prepared in a simple and efficient one-pot procedure by the addition of Grignard reagents to a series of aliphatic, aromatic and heteroaromatic nitriles. The resulting magnesium imines are subsequently converted to the desired amine after treatment with Ti(Oi-Pr)4 and additional microwave heating. Key to this procedure is the use of microwave heating for both steps of the reaction protocol, which significantly improves both reaction yields and reduces reaction times. In general, the Grignard addition reaction is complete within 5-10 min at 100 °C followed by conversion with Ti(Oi-Pr)4 and additional microwave heating to give the target amines in good yields.
One-pot synthesis of primary tert-alkylamines by the addition of organometallic reagents to nitriles mediated by Ti(Oi-Pr)4
Tomashenko, Olesya,Sokolov, Viktor,Tomashevskiy, Alexander,De Meijere, Armin
, p. 652 - 654 (2007/10/03)
A number of primary tert-alkylamines (18 examples, 25-72% yields) have been prepared according to a simple one-pot procedure by the addition of organometallic reagents such as Grignard reagents and organolithium compounds to nitriles in the presence of Ti(Oi-Pr)4. Georg Thieme Verlag Stuttgart.
