110-94-1Relevant articles and documents
Visible photorelease of liquid biopsy markers following microfluidic affinity-enrichment
Brown, Virginia,Digamber, Rane,Givens, Richard S.,Jackson, J. Matt,Pahattuge, Thilanga N.,Perera, Chamani,Peterson, Blake R.,Soper, Steven A.,Wijerathne, Harshani,Witek, Malgorzata A.
, p. 4098 - 4101 (2020)
We detail a heterobifunctional, 7-aminocoumarin photocleavable (PC) linker with unique properties to covalently attach Abs to surfaces and subsequently release them with visible light (400-450 nm). The PC linker allowed rapid (2 min) and efficient (>90%) release of CTCs and EVs without damaging their molecular cargo.
A Janus-type Heterogeneous Surfactant for Adipic Acid Synthesis
Antonyuk, Sergiy,Breuninger, Paul,Ernst, Stefan,Thiel, Werner R.,Vafaeezadeh, Majid,Wilhelm, Christian
, (2020)
A highly water-dispersible heterogeneous Br?nsted acid surfactant was prepared by synthesis of a bi-functional anisotropic Janus-type material. The catalyst comprises ionic functionalities on one side and propyl-SO3H groups on the other. The novel material was investigated as a green substitute of a homogeneous acidic phase transfer catalyst (PTC). The activity of the catalyst was investigated for the aqueous-phase oxidation of cyclohexene to adipic acid with 30 % hydrogen peroxide even in a decagram-scale. It can also be used for the synthesis of some other carboxylic acid derivatives as well as diethyl phthalate.
Clean Adipic Acid Synthesis from Liquid-Phase Oxidation of Cyclohexanone and Cyclohexanol Using (NH4)xAyPMo12O40 (A: Sb, Sn, Bi) Mixed Heteropolysalts and Hydrogen Peroxide in Free Solvent
Mouheb, Lynda,Dermeche, Leila,Mazari, Tassadit,Benadji, Siham,Essayem, Nadine,Rabia, Chérifa
, p. 612 - 620 (2018)
Abstract: Clean synthesis of adipic acid (AA) from oxidation of cyclohexanone, cyclohexanol or mixture cyclohexanol/cyclohexanone, was carried out at 90?°C, in the presence of hydrogen peroxide (30%) in free solvent, using Keggin-type polyoxometalates, (NH4)xAyPMo12O40 (An+=Sb3+, Bi3+ or Sn2+), as catalysts. HPLC analysis of reaction mixture showed the formation of adipic, succinic and glutaric acids and unidentified products. The salts were found to be effective for AA synthesis. Whatever the composition of the catalyst, the alcohol oxidation favors the formation of the unidentified products, unlike the ketone oxidation which favors that of the adipic acid. (NH4)0.5Sn1.25PMo12O40 led to the highest AA yield (56%) from cyclohexanone oxidation, after 20?h of reaction. In addition, 31P NMR analysis showed that it has conserved the Keggin structure contrary to others catalysts and that it can be used at least 3 times with reaction times of 20?h, without regeneration. From different catalytic tests and 31P NMR data, reaction pathways have been proposed. The active species could be peroxo-polyoxometalates.
Tungsten doped mesoporous SBA-16 as novel heterogeneous catalysts for oxidation of cyclopentene to glutaric acid
Jin, Manman,Zhang, Guodi,Guo, Zhenmei,Lv, Zhiguo
, (2018)
Novel heterogeneous tungsten species in mesoporous silica SBA-16 catalysts based on ship-in-a-bottle methodology are originally reported for oxidizing cyclopentene (CPE) to glutaric acid (GAC) using hydrogen peroxide (H2O2). For all W-SBA-16 catalysts, isolated tungsten species and octahedrally coordinated tungsten oxide species are observed while WO3 crystallites are detected for the W-SBA-16 catalysts with Si/ W = 5, 10, and 20. The specific surface areas and the corresponding total pore volumes decrease significantly as increasing amounts of tungsten incorporated into the pores of SBA-16. Using tungsten-substituted mesoporous SBA-16 heterogeneous catalysts, high yield of GAC (55%) is achieved with low tungsten loading (for Si/W = 30, ~13?wt%) for oxidation of CPE. The W-SBA-16 catalysts with Si/W = 30 can be reused five times without dramatic deactivation. In fact, low catalytic activity provided by bulk WO3 implies that the highly distributed tungsten species in SBA-16 and the steric confinement effect of SBA-16 are key elements for the outstanding catalytic performance.
Enantiotopically Selective Oxidation of α,ω-Diols with the Enzyme Systems of Microorganisms
Ohta, Hiromichi,Tetsukawa, Hatsuki,Noto, Naoko
, p. 2400 - 2404 (1982)
Gluconobacter were found to be capable of oxidizing prochiral diols such as 2-substituted propane-1,3-diols 1 and 3-substituted pentane-1,5-diols 4 with distinction of pro-R and pro-S sites of the molecules, in that (-)-(R)-α-substituted β-hydroxypropionic acids 2 and (+)-(3S)-3-substituted δ-valerolactones 5 were obtained, respectively.Oxidation of 3-methylpentane-1,3,5-triol 11 afforded unnatural (+)-(S)-mevalonolactone 12.The steric bulkiness of the substituents on the prochiral center and the distance from the hydroxy group greatly affected the rate and the enantioselectivity of the reaction.
Metal ion catalysis in the hydrolysis of esters of 2-hydroxy-1, 10-phenanthroline: The effects of metal ions on intramolecular carboxyl group participation
Fife, Thomas H.,Pujari
, p. 357 - 373 (2000)
Rate constants have been determined for hydrolysis of the acetate, glutarate, and phthalate monoesters of 2-hydroxy-1,10-phenanthroline in water at 30°C and μ = 0.1 M with KCl. The hydrolysis reactions of the esters are hydroxide ion catalyzed at pH > 9. The phthalate and glutarate monoesters have in addition pH-independent reactions from pH 5.5 to 9 that involve intramolecular participation by the neighboring carboxylate anion. The pH-independent reaction of the glutarate monoester is ～5-fold faster than that of the phthalate monoester. The plots of log kobsd vs pH for hydrolysis of the carboxyl substituted esters are bell shaped at pH a rapid reaction of the zwitterionic species (carboxyl anion and protonated phenanthroline nitrogen). The divalent metal ions, Cu2+, Ni2+, Zn2+, and Co2+, complex strongly with the esters; saturation occurs at metal ion concentrations less than 0.01 M. The 1:1 metal ion complexes have greatly enhanced rates of hydrolysis; the second-order rate constants for the OH- reactions are increased by factors of 105 to 108 by the metal ion. The pH-rate constant profiles for the phthalate and glutarate ester metal ion complexes have a sigmoidal region below pH 6 that can be attributed to a metal ion-promoted carboxylate anion nucleophilic reaction. The carboxyl group reactions are enhanced 102- to 103-fold by the metal ions, which allows the neighboring group reaction to be competitive with the favorable metal ion-promoted OH- reaction at pH 6. The half-lives of the pH-independent neighboring carboxyl group reactions of the Cu(II) complexes at 30°C are ～2 s. The other metal ion complexes are only slightly less reactive (half-lives vary from 2.5 to 40 s). These are the most rapid neighboring carboxyl group reactions that have been observed in ester hydrolysis.
MIL-101 metal-organic framework: A highly efficient heterogeneous catalyst for oxidative cleavage of alkenes with H2O2
Saedi, Zahra,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
, p. 18 - 22 (2012)
In the present work, a new and efficient method for direct oxidation of alkenes to carboxylic acids with H2O2 catalyzed by metal-organic framework MIL-101 is reported. In this transformation, the MIL-101 catalyzes the oxidation reactions by framework nodes and acts as a heterogeneous and reusable catalyst. The structure of MIL-101 was stable after three catalytic cycles.
Efficient oxidation of alcohols to carbonyl compounds with molecular oxygen catalyzed by N-hydroxyphthalimide combined with a Co species
Iwahama, Takahiro,Yoshino, Yasushi,Keitoku, Takashi,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 6502 - 6507 (2000)
Highly efficient catalytic oxidation of alcohols with molecular oxygen by N-hydroxyphthalimide (NHPI) combined with a Co species was developed. The oxidation of 2-octanol in the presence of catalytic amounts of NHPI and Co(OAc)2 under atmospheric dioxygen in AcOEt at 70 °C gave 2-octanone in 93% yield. The oxidation was significantly enhanced by adding a small amount of benzoic acid to proceed smoothly even at room temperature. Primary alcohols were oxidized by NHPI in the absence of any metal catalyst to form the corresponding carboxylic acids in good yields. In the oxidation of terminal vic-diols such as 1,2-butanediol, carbon-carbon bond cleavage was induced to give one carbon less carboxylic acids such as propionic acid, while internal vic-diols were selectively oxidized to 1,2-diketones.
Efficient synthesis of glutaric acid from L-glutamic acid via diazoniation/hydrogenation sequence
Zhang, Wei,Rao, Meng-Yun,Cheng, Zhong-Jun,Zhu, Xiao-Yan,Gao, Kai,Yang, Jian,Yang, Bo,Liao, Xia-Li
, p. 716 - 721 (2015)
The practical synthetic preparation of glutaric acid has remained a major challenge to date. In the present study, glutaric acid was synthesised by way of one-pot diazoniation/hydrogenation of the readily available L-glutamic acid under aqueous conditions on a gram-scale with good yields. This is the first example of the deamination of the aliphatic primary amine via diazoniation and could afford a practical approach to the production of glutaric acid.
Oxidation reactions catalysed by titanium- and chromium-containing silicalites
Raju, Satya V. N.,Upadhya,Ponrathnam,Daniel,Sudalai
, p. 1969 - 1970 (1996)
While the titanium silicalite-1 (TS-1)-tert-butyl hydroperoxide (TBHP) combination exhibits remarkable activity and selectivity in the oxidative cleavage of the C-C double bond of silyl enol ethers to produce dicarboxylic acids, the chemoselective oxidation of thioethers to sulfoxides without generation of sulfones is achieved using chromium silicalite-2 (CrS-2)-H2O2.
