5001-18-3Relevant academic research and scientific papers
Synthesis of adamantane-based trimeric cationic surfactants
Zhu, Hua,Guo, Jianwei,Yang, Chufen,Liu, Sa,Cui, Yingde,Zhong, Xing
, p. 1161 - 1167 (2013)
Three trimeric quaternary ammonium surfactants, having adamantane cores and different carbon chains, were synthesized using adamantane as the starting raw material. The target compounds were confirmed by elemental analysis, 1H NMR, 13C NMR, and mass spectroscopy. The influences of reaction conditions on the yields of the key intermediate product 1,3,5-trihydroxyadamantane (3) were investigated. Surface properties of the target compounds were measured. The critical micelle concentration values of 1a, 1b, and 1c were 2mM, 1mM, and 0.5mM, respectively.
Oxidations by methyl(trifluoromethyl) dioxirane. 3. Selective polyoxyfunctionalization of adamantane
Mello, Rossella,Cassidei, Luigi,Fiorentino, Michele,Fusco, Caterina,Curci, Ruggero
, p. 3067 - 3070 (1990)
Adamantane (1) can be converted directly into adamantan-1,3,5-triol (5) and into adamantan-1,3,5,7-tetraol (6) under remarkably mild conditions by employing an excess of isolated methyl (trifluoromethyl)dioxirane (3a) in solution. This new dioxirane species was found to be over 7,000-fold more reactive than dimethyldioxirane (3b) in performing adamantane hydroxylations.
Photoassisted oxygenation of alkane catalyzed by ruthenium complexes using 2,6-dichloropyridine N-oxide under visible light irradiation
Yamaguchi, Motowo,Kumano, Takashi,Masui, Dai,Yamagishi, Takamichi
, p. 798 - 799 (2004)
The chloro(Me2SO)ruthenium(II) complexes with tris(2-pyridylmethyl)amine or its derivative catalyses the selective, stereospecific, and photoregulative alkane oxidation in the presence of 2,6-dichloropyridine N-oxide under visible light irradiation.
Synthesis and properties of novel cationic gemini surfactants with adamantane spacer
Xu, Xiao-Jian,Guo, Jian-Wei,Zhong, Xing
, p. 367 - 369 (2014)
Novel quaternary ammonium cationic gemini surfactants, with two hydrocarbon chains and an adamantane core, were designed and synthesized by three-step reactions from adamantane. The structure of obtained surfactants were confirmed by 1H NMR, FTIR and elements analysis and the surface properties of these surfactants were also studied by surface tension measurements. These target surfactants exhibit much lower critical micelle concentrations (CMC) and higher efficiency in lowering the surface tension of water than typical surfactants.
Selective biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora (I.M.I. 342950)
Bailey, Patrick D.,Higgins, Stanley D.,Ridyard, Colin H.,Roberts, Stanley M.,Rosair, Georgina M.,Whittaker, Roger A.,Willetts, Andrew J.
, p. 1833 - 1834 (1996)
The biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora in a whole-cell oxidation system exclusively generated 3-hydroxy and 4ax-hydroxy derivatives; the assignments were confirmed by three X-ray crystal structure determinations.
Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with transition metal salts
Ishii, Yasutaka,Kato, Susumu,Iwahama, Takahiro,Sakaguchi, Satoshi
, p. 4993 - 4996 (1996)
Adamantanes were successfully converted into the corresponding mono- and dihydroxy adamantanes with molecular oxygen in the presence of N- hydroxyphthalimide (NHPI) combined with cobalt salts under mild conditions. For example, exposure of adamantane under oxygen atmosphere in the presence of NHPI (10 mol%) and Co(acac)2 (0.5 mol%) in acetic acid at 75 °C for 6 h afforded adamantan-1-ol (43 %) and adamantane-1,3-diol (40 %) along with adamantan-2-one (8 %) in 93 % conversion. Similarly, 1,3-dimethyladamantane produced 3,5-dimethyladamantan-1-ol (47 %) and 5,7-dimethyladamantane-1,3- diol (37 %).
Ruthenium-Immobilized Periodic Mesoporous Organosilica: Synthesis, Characterization, and Catalytic Application for Selective Oxidation of Alkanes
Ishito, Nobuhiro,Kobayashi, Hirokazu,Nakajima, Kiyotaka,Maegawa, Yoshifumi,Inagaki, Shinji,Hara, Kenji,Fukuoka, Atsushi
, p. 15564 - 15569 (2015)
Periodic mesoporous organosilica (PMO) is a unique material that has a crystal-like wall structure with coordination sites for metal complexes. A Ru complex, [RuCl2(CO)3]2, is successfully immobilized onto 2,2'-bipyridine (BPy) units of PMO to form a single-site catalyst, which has been confirmed by various physicochemical analyses. Using NaClO as an oxidant, the Ru-immobilized PMO oxidizes the tertiary C-H bonds of adamantane to the corresponding alcohols at 57 times faster than the secondary C-H bonds, thereby exhibiting remarkably high regioselectivity. Moreover, the catalyst converts cis-decalin to cis-9-decalol in a 63% yield with complete retention of the substrate stereochemistry. The Ru catalyst can be separated by simple filtration and reused without loss of the original activity and selectivity for the oxidation reactions.
Method for preparing 1,3-adamantane diol by taking 1-bromo-adamantane as initial raw material
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Paragraph 0085-0090, (2021/01/25)
The invention discloses a method for preparing 1,3-adamantane diol by taking 1-bromo-adamantane as an initial raw material, which comprises the following steps: (1) dissolving 1-bromo-adamantane in anorganic solvent, and adding concentrated sulfuric acid and nitric acid to carry out nitration reaction, thereby obtaining an organic solution phase; and (2) mixing the obtained organic solution phasewith a water solution of a strong base, and carrying out a hydrolysis reaction to obtain the product. According to the method, the 1,3-adamantane diol is synthesized by taking 1-bromo-adamantane which is easily available and low in cost as an initial raw material, so that the defects of high production cost and complex separation and purification of a target product in an existing industrial production process taking the 1,3-dibromo adamantane as a raw material are overcome; particularly, the mixed acid phase and the alkaline water liquid phase can be recycled and adjusted for multiple times,so that the environment-friendly treatment cost of the production waste is greatly reduced.
Method for preparing 1,3-adamantanediol by taking 1-adamantanol as initial raw material
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Paragraph 0053-0118, (2021/01/29)
The invention discloses a method for preparing 1,3-adamantanediol by using 1-adamantanol as an initial raw material. The method comprises the following steps: (1) mixing 1-adamantanol with a mixed acid solution of fuming sulfuric acid, acetic anhydride and nitric acid, carrying out nitration reaction, and diluting the reacted material with clear water to terminate the reaction; (2) heating the material water liquid after the nitration reaction is ended, and introducing gas; (3) adding powdery activated carbon into the termination material into which the gas is introduced, adding clear water tofurther dilute the sulfuric acid solution, and separating precipitates from the acid solution; and (4) mixing the precipitate separated in the step (3) with strong base, alkalizing and hydrolyzing toobtain the product. The method has the advantages of easily available initial raw materials, high product yield, low production cost, safety, environmental protection, and facilitation of industrialpromotion and application.
Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds
Doiuchi, Daiki,Uchida, Tatsuya
supporting information, p. 7301 - 7305 (2021/10/01)
We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)2 and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation. Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C-H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as d-[3-17O/18O]-mannose can be prepared in a multigram scale.
