101-02-0Relevant articles and documents
The local structure of triphenyl phosphite studied using spallation neutron and high-energy X-ray diffraction
Mei, Qiang,Ghalsasi, Prasanna,Benmore, Chris J.,Yarger, Jeffery L.
, p. 20076 - 20082 (2004)
Spallation neutron and high-energy X-ray diffraction experiments have been performed to investigate the local structural changes in triphenyl phosphite (TPP) in the crystalline, glacial, glassy, and supercooled liquid phases. The hydrogen/deuterium first-order difference method shows a large increase in intensity due to additional hydrogen correlations in the crystalline spectra compared to the glass and supercooled liquid at a??3.0 and 3.4 Aì?. These features are shown to be largely due to inter-phenyl ring H-C/H interactions, which are probably associated in part with the formation of weak intermolecular hydrogen bonds. The high-energy X-ray diffraction data show a decrease in correlations at 3.12 Aì? which is attributed to changes in C-O/P intramolecular interactions between the glacial and crystalline forms. The structural evolution of the glacial state was also measured over time using total neutron diffraction. The largest structural differences between the early glacial and crystalline states are observed at 3.0 and 4.5 Aì?. Moreover, as the transformation progresses, the glacial spectra cannot be adequately described as a simple mixture of supercooled liquid and crystalline components. These results suggest that changes in molecular conformation and nearest-neighbor interactions are responsible for the existence of the glacial state.
Ruthenium-catalyzed regio- And site-selective: Ortho C-H borylation of phenol derivatives
Homma, Yuki,Fukuda, Kazuishi,Iwasawa, Nobuharu,Takaya, Jun
, p. 10710 - 10713 (2020)
Efficient synthesis of o-borylphenols is achieved through the Ru-catalyzed regio- and site-selective sp2 C-H borylation of aryl diphenylphosphinites followed by removal of the phosphorus directing group. A successful application to aryl phosphites enables practical one-pot borylation of phenols, demonstrating high synthetic utility of this protocol.
Avar,Neumann
, p. 215,222, 223 (1977)
Selective deoxygenation of aryl selenoxides by triaryl phosphites. Evidence for a concerted transformation
Stratakis, Manolis,Rabalakos, Constantinos,Sofikiti, Nikoletta
, p. 349 - 351 (2003)
Triaryl phosphites selectively reduce aryl selenoxides to selenides. The Hammett plot of the reactions of para-phenyl substituted triaryl phosphites with diphenyl selenoxide gave ρ=+2.3, whereas with bis(p-methoxyphenyl) selenoxide, ρ=-2.1. The results are consistent with a concerted mechanism for the oxygen transfer from Se to P.
REACTION OF ELEMENTAL PHOSPHORUS WITH PHENOLS
Ivanov, B. E.,Badeeva, E. K.,Krokhina, S. S.
, p. 2371 - 2373 (1988)
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Gottlieb
, p. 748,750 (1932)
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Substituent effects on the 31P NMR chemical shifts of arylphosphorothionates
Hernández, Javier,Goycoolea, Francisco M.,Zepeda-Rivera, Denisse,Juárez-Onofre, Josué,Martínez, Karla,Lizardi, Jaime,Salas-Reyes, Magali,Gordillo, Bárbara,Velázquez-Contreras, Carlos,García-Barradas, Oscar,Cruz-Sánchez, Samuel,Domínguez, Zaira
, p. 2520 - 2528 (2006)
Six tris(aryloxy)phosphorothionates substituted in the para position of the aromatic rings were synthesized and studied by 31P NMR, X-ray diffraction techniques and ab initio calculations at a RHF/6-31G** level of theory, in order to find the main structural factors associated with the δ31P in these compounds. As the electron-withdrawing (EW) ability of the substituents was increased, an 'abnormal' shielding effect on δ31P of the arylphosphorothionates was observed. The analyses of the geometrical properties obtained through both experimental and theoretical methods showed that a propeller-type conformation is preferred for the arylphosphorothionates, except in the case of the tris(O-4-methylphenyl) phosphorothionate, since one of the aromatic rings is not rotated in the same direction as the other two in the solid state. The main features associated with the δ31P NMR of compounds 1-6 were a decrease of the averaged O-P-O angle and mainly the shortening of the PS bond length, which is consistent with an increase of the thiophosphoryl bond order as δ31P values go upfield. On the other hand, comparison of the experimental and calculated bond lengths and bond angles involving α bonded atoms to phosphorus of the six compounds suggested that stereoelectronic interactions of the type nπO-σ*PS, nπO- σ*P-OAr and nπS-σ* P-OAr could be present in the arylphosphorothionates 1-6.
A novel mild deprotection method for phosphine-boranes
Schroeder, Marc,Nozaki, Kyoko,Hiyama, Tamejiro
, p. 1931 - 1932 (2004)
Treatment of phosphine-boranes with molecular sieves 4A in a mixture of an ethereal solvent and an alcohol provided deprotected free phosphines in quantitative yields. The phosphines can be obtained by a simple filtration/crystallization procedure in most cases. It should be noted that the current method is successfully applied to the deprotection of a phosphite-borane for the first time.
Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus
Zhang, Yue,Cai, Ziman,Chi, Yangyang,Zeng, Xiangzhe,Chen, Shuanghui,Liu, Yan,Tang, Guo,Zhao, Yufen
supporting information, p. 5158 - 5163 (2021/07/20)
Industrially important triaryl phosphites, traditionally prepared from PCl3, have been synthesized by a diphenyl diselenide-catalyzed one-step procedure involving white phosphorus and phenols, which provides a halogen- and transition metal-free way to these compounds. Subsequent oxidation of triaryl phosphites produces triaryl phosphates and triaryl thiophosphates. Phosphorotrithioates are also prepared efficiently from aromatic thiols and aliphatic thiols.
Phosphonic Analogs of Alanine as Acylpeptide Hydrolase Inhibitors
Walczak, Maciej,Chryplewicz, Agnieszka,Olewińska, Sandra,Psurski, Mateusz,Winiarski, ?ukasz,Torzyk, Karolina,Oleksyszyn, Józef,Sieńczyk, Marcin
, (2021/02/01)
Acylpeptide hydrolase is a serine protease, which, together with prolyl oligopeptidase, dipeptidyl peptidase IV and oligopeptidase B, belongs to the prolyl oligopeptidase family. Its primary function is associated with the removal of N-acetylated amino acid residues from proteins and peptides. Although the N-acylation occurs in 50–90 % of eukaryotic proteins, the precise functions of this modification remains unclear. Recent findings have indicated that acylpeptide hydrolase participates in various events including oxidized proteins degradation, amyloid β-peptide cleavage, and response to DNA damage. Considering the protein degradation cycle cross-talk between acylpeptide hydrolase and proteasome, inhibition of the first enzyme resulted in down-regulation of the ubiquitin-proteasome system and induction of cancer cell apoptosis. Acylpeptide hydrolase has been proposed as an interesting target for the development of new potential anticancer agents. Here, we present the synthesis of simple derivatives of (1-aminoethyl)phosphonic acid diaryl esters, phosphonic analogs of alanine diversified at the N-terminus and ester rings, as inhibitors of acylpeptide hydrolase and discuss the ability of the title compounds to induce apoptosis of U937 and MV-4-11 tumor cell lines.
