- REACTION MECHANISMS FOR ELECTROCHEMICAL CARBON-SKELETON REARRANGEMENT AS CATALYZED BY HYDROPHOBIC VITAMIN B12 IN NONAQUEOUS MEDIA
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Reaction mechanisms for the controlled-potential electrolysis of 2,2-bis(ethoxycarbonyl)-1-bromopropane at -1.0, -1.5, and -2.0 V vs.SCE as catalyzed by a hydrophobic vitamin B12 were clarified.
- Murakami, Yukito,Hisaeda, Yoshio,Tashiro, Takako,Matsuda, Yoshihisa
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- Radical Heterocyclization and Heterocyclization Cascades Triggered by Electron Transfer to Amide-Type Carbonyl Compounds
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Radical heterocyclizations triggered by electron transfer to amide-type carbonyls, using SmI2-H2O, provide straightforward access to bicyclic heterocyclic scaffolds containing bridgehead nitrogen centers. Furthermore, the first radical heterocyclization cascade triggered by reduction of amide-type carbonyls delivers novel, complex tetracyclic architectures containing five contiguous stereocenters with excellent diastereocontrol.
- Huang, Huan-Ming,Procter, David J.
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- Preparation and Characterisation of a Bis-μ-Hydroxo-NiIII 2 Complex
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Hydroxide-bridged high-valent oxidants have been implicated as the active oxidants in methane monooxygenases and other oxidases that employ bimetallic clusters in their active site. To understand the properties of such species, bis-μ-hydroxo-NiII 2 complex (1) supported by a new dicarboxamidate ligand (N,N′-bis(2,6-dimethyl-phenyl)-2,2-dimethylmalonamide) was prepared. Complex 1 contained a diamond core made up of two NiII ions and two bridging hydroxide ligands. Titration of the 1 e? oxidant (NH4)2[CeIV(NO3)6] with 1 at ?45 °C showed the formation of the high-valent species 2 and 3, containing NiIINiIII and NiIII 2 diamond cores, respectively, maintaining the bis-μ-hydroxide core. Both complexes were characterised using electron paramagnetic resonance, X-ray absorption, and electronic absorption spectroscopies. Density functional theory computations supported the spectroscopic assignments. Oxidation reactivity studies showed that bis-μ-hydroxide-NiIII 2 3 was capable of oxidizing substrates at ?45 °C at rates greater than that of the most reactive bis-μ-oxo-NiIII complexes reported to date.
- Spedalotto, Giuseppe,Gericke, Robert,Lovisari, Marta,Farquhar, Erik R.,Twamley, Brendan,McDonald, Aidan R.
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- 1,2-Migrations in Free Radicals Related to Coenzyme B12 Dependent Rearrangements
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The free radicals XC(CH3)(COOR)CH2., where X=C(=O)Me (1), C(=O)SEt (2), C(=O)OEt (3), C(=CH2)Me (4), and C6H5 (5), were generated by reaction of the corresponding bromides with (n-Bu)3SnH.The rates of rearrangement involving 1,2-migration of X (to form .C(CH3)(COOR)(CH2X)) were measured in competition with trapping by (n-Bu)3SnH.The measurements yielded the following rearrangement rate constants, kr, and activation parameters, ΔH+ and ΔS+: (1) 1.2E4 s-1 at 45 deg C, 11.0 kcal/mol, -4 cal/mol.K; (2) 23.5 s-1 at 60.5 deg C, 13.8 kcal/mol, -11 cal/mol.K; (3) -1 at 113 deg C; (4) 3.0E5 s-1 at 45 deg C, 10.0 kcal/mol, -2 cal/mol.K; (5) 5.0E3 s-1 at 61 deg C.From the results of crossover experiments it is concluded that the rearrangements of 1 and 2 are intramolecular processes, probably proceeding through cyclopropyloxy radical intermediates or transition states.The carbanions corresponding to 1-5 (i.e., XC(CH3)(COOR)CH2-, generated by reduction of the corresponding bromides with sodium naphthalene) also rearrange rapidly but, in each case, with some contribution from migration of the ester group.This represents the first demonstration of spontaneous 1,2-migration of a thioester group in a free radical and models the coenzyme B12 dependent methylmalonyl-CoA mutase rearrangement.The results support a free-radical rearrangement mechanism for the latter reaction.
- Wollowitz, Susan,Halpern, Jack
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- Characterization of a Simple Vitamin B12 Model Complex and Its Catalysis in Electrochemical Carbon-Skeleton Rearrangement
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The electrochemical carbon-skeleton rearrangement reaction of 2,2-bis(ethoxycarbonyl)-1-bromopropane was catalyzed by the cobalt complex of 2,10-diethyl-3,9-dipropyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraene-1,10-diol, which was characterized by ESR spectroscopy and cyclic voltammetry.
- Murakami, Yukito,Hisaeda, Yoshio,Fan, Sheng-Di
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Read Online
- Preparation method for 5,5-dimethylbarbituric acid as impurity of butalbital
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The invention belongs to the technical field of pharmaceutical synthesis, and particularly relates to a preparation method for 5,5-dimethylbarbituric acid as an impurity of butalbital. In a sodium ethoxide/ethanol system, diethyl methylmalonate is dripped, and stirring is carried out; iodomethane is then dripped, and after reaction, crude 2,2-diethyl dimethylmalonate is obtained; the obtained crude 2,2-diethyl dimethylmalonate reacts with urea in a sodium ethoxide/ethanol system, and after reaction is completed, 5,5-dimethylbarbituric acid is obtained by post-processing. The raw materials of the invention are easy to obtain, the preparation method is easy to operate, the safety of reaction is high, post-processing is simple, the purity of prepared 5,5-dimethylbarbituric acid as an impurity of butalbital is high, reaching 99.40 percent or more, and the preparation method has an important guiding significance for the research of butalbital preparations.
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Paragraph 0026; 0034; 0040; 0041
(2017/08/31)
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- Process for the alkylation of active methylene compounds
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The invention discloses an alkylation method of an active methylene compound. The method comprises the following steps: A, adding the active methylene compound to an inorganic alkali-first polar organic solvent mixing system to form a to-be-reacted mixture; B, adding an alkylating agent to the to-be-reacted mixture, filtering after reacting to obtain filtrate, and removing a solvent in the filtrate to obtain the alkylated active methylene compound. According to the method, the inorganic alkali is adopted as a proton abstraction reagent of the active methylene compound, so that the removal effect on alpha-hydrogen in the active methylene compound can be ensured, the alkylation reaction of the active methylene compound can be carried out under a mild condition, and the reaction safety is improved. Meanwhile, the inorganic alkali is low in price, so that the production cost of the alkylation reaction is reduced.
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Paragraph 0211-0215
(2017/02/24)
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- Discovery of potent c-MET inhibitors with new scaffold having different quinazoline, pyridine and tetrahydro-pyridothienopyrimidine headgroups
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Cellular mesenchymal-epithelial transition factor (c-MET) is closely linked to human malignancies, which makes it an important target for treatment of cancer. In this study, a series of 3-methoxy-N-phenylbenzamide derivatives, N-(3-(tert-butyl)-1-phenyl-1H-pyrazol-5-yl) benzamide derivatives and N1-(3-fluoro-4-methoxyphenyl)-N3-(4-fluorophenyl) malonamide derivatives were designed and synthesized, some of them were identified as c-MET inhibitors. Among these compounds with new scaffolds having different quinazoline, pyridine and tetrahydro-pyridothienopyrimidine head groups, compound 11c, 11i, 13b, 13h exhibited both potent inhibitory activities against c-MET and high anticancer activity against tested cancer cell lines in vitro. In addition, kinase selectivity assay further demonstrated that both 13b and 13h are potent and selective c-MET inhibitors. Molecular docking supported that they bound well to c-MET and VEGFR2, which demonstrates that they are potential c-MET RTK inhibitors for cancer therapy.
- Jiang, Yingnan,Zhang, Ke,Gao, Suyu,Wang, Guihua,Huang, Jian,Wang, Jinhui,Chen, Lixia
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- PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF
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This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.
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Page/Page column 101
(2015/07/07)
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- Design of bisquinolinyl malonamides as Zn2+ ion-selective fluoroionophores based on the substituent effect
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A series of malonamides possessing two quinoline moieties were synthesized and characterized as fluoroionophores for the Zn2+ ion. We focused on the relationship between the substituents introduced to the C2-position of the malonamides and their Zn2+ ion-selectivity, exploiting the structural effect of the substituents in the design of the fluoroionophores with high selectivity. The substituents introduced to the malonamides were the methyl, benzyl and naphthalenylmethyl groups. In dimethyl sulfoxide solvent, all substituted bisquinolinyl malonamides showed excellent fluorescence sensing for the Zn2+ ion, while unsubstituted bisquinolinyl malonamide 1 displayed ratiometric sensing for the Co2+ ion. N,N′-Bis(8-quinolyl)-2-methyl-2-naphthalenylmethyl malonamide 4 exhibited the highest Zn2+ ion-selectivity against the Cd2+ ion. Although the substituents introduced into the C2-position are spatially distant from the quinoline recognition moiety, this study indicated that they greatly influenced the ion selectivities of the bisquinolinyl malonamides. Furthermore, it was demonstrated that visible fluorescence analyses could be performed on malonamide 4.
- Moriuchi-Kawakami, Takayo,Kawata, Keita,Nakamura, Sho,Koyama, Yoshiaki,Shibutani, Yasuhiko
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p. 9805 - 9813
(2015/01/09)
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- 9-AMINOMETHYL SUBSTITUTED TETRACYCLINE COMPOUNDS
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The present invention relates to 9-aminomethyl substituted tetracycline compounds represented by formula (I), or pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, as well as a method for preparing these compounds and a pharmaceutical composition comprising the same. The present invention relates also to a use of these compounds in the preparation of a medicament for the treatment and/or prophylaxis of tetracycline drug-sensitive disease. wherein, R2a, R2b, R3, R4a, R4b, R5, R6a, R6b, R7, R8, R9a, R9b, R10, R11, R12, R13a and R13b are each independently as defined in the description.
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(2014/07/08)
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- 9-AMINOMETHYL SUBSTITUTED TETRACYCLINE COMPOUND
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The present invention relates to 9-aminomethyl substituted tetracycline compounds represented by formula (I), or pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, as well as a method for preparing these compounds and a pharmaceutical composition comprising the same. The present invention relates also to a use of these compounds in the preparation of a medicament for the treatment and/or prophylaxis of tetracycline drug-sensitive disease. wherein, R2a, R2b, R3, R4a, R4b, R5, R6a, R6b, R7, R8, R9a, R9b, R10, R11, R12, R13a and R13b are each independently as defined in the description.
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Paragraph 0080-0081
(2014/06/24)
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- β-aryl nitrile construction via palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts
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The palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts with benzyl electrophiles was discovered. This reaction exhibits good functional group compatibility and proceeds under relatively mild conditions. A diverse range of quaternary, tertiary and secondary β-aryl nitriles can be conveniently prepared by this method. Copyright
- Shang, Rui,Huang, Zheng,Xiao, Xiao,Lu, Xi,Fu, Yao,Liu, Lei
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supporting information
p. 2465 - 2472,8
(2020/08/31)
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- Utilising 14C-radiolabelled atom transfer radical polymerisation initiators
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14C-radio-initiated atom transfer radical polymerisations allow direct monitoring of the fate of initiating species.
- Long, Mark,Thornthwaite, David W.,Rogers, Suzanne H.,Bonzi, Gwenaelle,Livens, Francis R.,Rannard, Steve P.
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supporting information; experimental part
p. 6406 - 6408
(2010/03/04)
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- Effect of supramolecular inclusion on the 1,2-rearrangement of free radicals
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The free radicals 3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl (1′) and 3-ethoxy-2-(ethoxycarbonyl)-2-methyl-3-oxopropyl (2′) were generated by photolysis of perester precursors in i) hexane solution, ii) in the presence of β-cyclodextrin, and iii) in NaY zeolite. While free radicals in solution are reluctant to rearrange, they do so when encapsulated in β-cyclodextrin or NaY zeolite. The coenzyme-B12-dependent enzymic rearrangement of methylmalonyl-CoA to succinyl-CoA could be mimicked by photochemical generation of an analogue of the putative intermediate radical in a molecular container.
- Chen, Ying,Kervio, Eric,Retey, Janos
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p. 552 - 558
(2007/10/03)
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- Synthesis and spectroscopic characterisation of 13C-labelled ubiquinone-0 and ubiquinone-10
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(1-13C)-, (2-13C)-, (3-13C)-, (3-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-10 and the corresponding (1-13C)-, (6-13C)-, (5-13C)-, (5-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-0 have been synthesised from simple labelled starting materials via a single reaction scheme.The ubiquinones have been characterised using mass spectrometry, 1H NMR and 13C NMR.The spectroscopic results indicate that, within experimental error, the syntheses have been accomplished without scrambling or dilution of label.All labelled ubiquinones have been synthesised on a decigram scale.
- Liemt, W. B. S. van,Steggerda, W. F.,Esmeijer, R.,Lugtenburg, J.
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p. 153 - 162
(2007/10/02)
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- Surface-mediated Solid-phase Reaction. Part 2. Highly Selective Mono- and Di-C-alkylation of 1,3-Dicarbonyl Compounds on the Surface of Alumina
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Highly selective mono- and di-C-alkylation of 1,3-dicarbonyl compounds with different, structurally varied alkyl halides has been achieved in high yields through a simple solvent-free reaction on the surface of alumina impregnated with sodium or potassium alkoxide.
- Ranu, Brindaban C.,Bhar, Sanjay
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p. 365 - 368
(2007/10/02)
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- Electroorganic Chemistry. 124. Electroreductive Intramolecular Coupling of α-(ω-Bromoalkyl) β-Keto Esters
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Intramolecular coupling occurs when cyclic α-(bromomethyl) β-keto esters are electrochemically reduced in the presence of trimethylsilyl chloride and one-carbon ring-enlarged products are obtained in reasonable yields.Electroreduction of α-(γ-bromopropyl) β-keto esters also affords the corresponding five-membered cyclized products and/or the corresponding ring-opened compounds.The ease of ring opening of the cyclized products is highly influenced by their stereoconfiguration.Electroreduction of α-(β-bromoethyl) β-keto ester gives the product formed by the reductive elimination of the bromoethyl group whereas α-(δ-bromobutyl) β-keto ester yields the product of the reductive elimination of bromine.This electroreductive intramolecular coupling is initiated by the reduction of the carbon-bromine bond and proceeds through a carbanion intermediate.
- Shono, Tatsuya,Kise, Naoki,Uematsu, Nobuyuki,Morimoto, Shinji,Okazaki, Eiichi
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p. 5037 - 5041
(2007/10/02)
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- Redox Behavior of Simple Vitamin B12 Model Complexes and Electrochemical Catalysis of Carbon-Skeleton Rearrangements
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Various cobalt complexes of 4,10-dipropyl-5,9-diazatrideca-4,9-diene-3,10-dione dioxime, (C2C3)(DOH)2pn, were prepared, and redox behavior of them was investigated by means of cyclic voltammetry; Co(II)/Co(I) redox potentials in the range of -0.69 through -0.7 V vs.Ag/AgCl.The monomethylated complex, which has a cobalt-carbon bond at one axial site of the nuclear cobalt, was disproportionated to the dimethylated complex, involving two cobalt-carbon bonds at both axial sites, and the CoI species by one-electron reduction.The dimethylated complex was inactive for electrochemical reduction, but transformed into the monomethylated complex via cleavage of a cobalt-carbon bond upon electrochemical oxidation.The electrolyses of 1-bromo-2,2-bis(ethoxycarbonyl)propane, 1-bromo-2-cyano-2-ethoxycarbonylpropane, and 2-acetyl-1-bromo-2-ethoxycarbonylpropane in the presence of IIIBr2> in N,N-dimethylformamide did not proceed in a divided cell at -2.0 vs.Ag/AgCl, since the corresponding dialkylated complexes, inactive for electrochemical reduction, were formed in the course of reaction.When imidazole was added to solutions for the electrolysis, the reaction proceeded efficiently by the trans effect arising from the coordinated axial base and the corresponding carbon-skeleton rearrangement products were obtained.On the other hand, the carbon-skeleton rearrangement proceeded in an undivided cell even in the absence of imidazole; the dialkylated complex was decomposed to give the monoalkylated complex and the reduction and rearrangement products by electrochemical ocxidation on the anode.
- Murakami, Yukito,Hisaeda, Yoshio,Fan, Sheng-Di,Matsuda, Yoshihisa
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p. 2219 - 2228
(2007/10/02)
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- Reactions of 2-, 3-, and 4-(N-Nitroso)methylaminopyridine with Esters Containing Active Methylene Groups
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2-N-Nitrosomethylaminopyridine but not 2-methylaminopyridine, 3-N-nitrosomethylamino- or 3-methylaminopyridine and 4-N-nitrosomethylamino- or 4-N-methylaminopyridine react with malonate esters to form the corresponding derivatives of carbamates, amides and dihydropyridines respectively.In the reaction of the 4-isomers with diisopropyl malonate small amounts of the corresponding carbamates was also formed.
- Kiriazis, L.,Kalatzis, E.,Alexandrou, N. E.
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p. 155 - 160
(2007/10/02)
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- REACTIONS RELATED TO COENZYME B12 DEPENDENT REARRANGEMENTS: METAL MEDIATED FREE RADICAL ACYL MIGRATIONS IN METHYL AND CYCLOPROPYL SUBSTITUTED MODELS
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Free radicals generated from the methylmalonylcoenzyme A mutase model substrates (3) and (4) by chromium(II) reduction, or by pyrolysis of the analogous cobaloximes, underwent -migration only in the acyl series (R=Ph, Me) and not the critical ester series (R=OEt, SBu).The mechanism of the migration was implied by incorporation into (4) of the cyclopropyl ring, the opening of which demonstrated the free radical nature of rearranged intermediate.
- Best, Wayne M.,Widdowson, David A.
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p. 5943 - 5954
(2007/10/02)
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- Carbon -Skeleton Rearrangement of an Alkyl Ligand Coordinated to Simple Vitamin B12 Model Complexes in Synthetic Bilayer Membrane
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The carbon-skeleton rearrangement of an alkyl ligand coordinated to the nuclear cobalt of simple vitamin B12 model complexes formed with diimine-dioxime-type ligands took place efficiently in a synthetic bilayer membrane under irradiation with visible light.
- Murakami, Yukito,Hisaeda, Yoshio,Song, Xi-Ming,Fan, Sheng-Di
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p. 877 - 880
(2007/10/02)
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- Electrochemical Carbon-skeleton Rearrangements catalysed by Hydrophobic Vitamin B12 immobilised in a Polymer-coated Electrode
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A glassy carbon electrode was coated with a polymer species derived from a hydrophobic vitamin B12 and Araldite CT-200, and the immobilised cobalt complex catalysed the electrochemical carbon-skeleton rearrangements of alkyl halides having electron-withdrawing groups.
- Murakami, Yukito,Hisaeda, Yoshio,Ozaki, Toshiaki,Matsuda, Yoshihisa
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p. 1094 - 1096
(2007/10/02)
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- Redox Behavior of Simple Vitamin B12 Model Complexes with Cobalt-Carbon Bonds and Catalytic Carbon-Skeleton Rearrangements
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The cobalt complex of 2,10-diethyl-3,9-dipropyl-1,4,8,11-tetraaazaundeca-1,3,8,10-tetraene-1,11-diol catalyzed electrolyses of alkyl halides with electron-withdrawing groups at the β-position to afford rearrangement products via oxidation of the corresponding dialkylated complexes as intermediates.
- Murakami, Yukito,Hisaeda, Yoshio,Fan, Sheng-Di,Matsuda, Yoshihisa
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p. 835 - 838
(2007/10/02)
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- Hydrophobic Vitamin B12. Part 6. Carbon-skeleton Rearrangement via Formation of Host-Guest Complexes derived from an 'Octopus Azaparacyclophane and hydrophobic Vitamin B12 Derivatives: a Novel Holoenzyme Model System
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The alkylation reactions of a hydrophobic vitamin B12 derivative with alkyl bromides in an 'octopus' azaparacyclophane having eight hydrocarbon chains have been investigated.Molecular discrimination has been shown to originate from electrostatic interaction between the octopus cyclophane and the alkyl bromides.Alkylation was enhanced by desolvation and proximity effects operating on the reacting species via formation of a ternary complex composed of the octopus cyclophane, the hydrophobic vitamin B12 derivative, and an alkyl halide.Carbon-skeleton rearrangement reactions of alkyl ligands bound to the hydrophobic vitamin B12 were found to be markedly favoured in the hydrophobic cavity provided by the octopus cyclophane, relative to the reactions in methanol and benzene, under anaerobic photolysis conditions at ordinary temperatures.The same reactions took place readily in solid benzene below 4 deg C under similar conditions.The central cobalt atom of the hydrophobic vitamin B12 participates in the rearrangement reaction via formation of a tight pair with an alkyl radical species.Non-enzymic rearrangement reactions have been shown here to proceed quite efficiently by employing a relevant apoenzyme model.
- Murakami, Yukito,Hisaeda, Yoshio,Kikuchi, Jun-ichi,Ohno, Teruhisa,Suzuki, Masashi,et al.
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p. 1237 - 1246
(2007/10/02)
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- Hydrophobic Vitamin B12. V. Electrochemical Carbon-Skeleton Rearrangement as Catalyzed by Hydrophobic Vitamin B12: Reaction Mechanisms and Migratory Aptitude of Functional Groups
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The carbon-skeleton rearrangements as catalyzed by heptamethyl cobyrinate perchlorate, 1ester>ClO4, were investigated under electrochemical conditions.The controlled-potential electrolysis of 2,2-bis(ethoxycarbonyl)-1-bromopropane, which is considered to be a model substrate for methylmalonyl-CoA mutase, was catalyzed by 1ester>ClO4 in N,N-dimethylformamide to give the rearrangement product, 1,2-bis(ethoxycarbonyl)propane, as a major one at -1.5 V vs.SCE in the presence of acetic acid and at potentials more cathodic than -1.8 V vs.SCE without acetic acid in the dark.The electrochemical carbon-skeleton rearrangement was postulated to proceed via formation of anionic intermediates.The electrolyses of 1-bromo-2-cyano-2-ethoxycarbonylpropane, 2-acetyl-1-bromo-2-ethoxycarbonylpropane, and 1-bromo-2-propane with 1ester>ClO4 also afforded the corresponding carbon-skeleton rearrangement products.The results indicated that substrates with two electron-withdrawing groups placed on the β-carbon atom with combination of one carboxylic ester and one of carboxylic ester, acetyl, and cyano moieties readily gave the corresponding rearrangement products which were derived from individual migration of the substituent groups.Substrates with only one of the electron-withdrawing groups, carboxylic ester, acetyl, and cyano, did not give any rearrangement product, but a substrate with one thioester group afforded the corresponding rearrangement product.The migratory aptitude of electron-withdrawing groups was found to decrease in the order: COSR>COR>COOR>CN.Both electronic character and steric bulkiness of the migrating groups are apparently reflected on this tendency, even though relative contributions of these effects are much dependent on the nature of β-substituents.
- Murakami, Yukito,Hisaeda, Yoshio,Ozaki, Toshiaki,Tashiro, Takako,Ohno, Teruhisa,et al.
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p. 311 - 324
(2007/10/02)
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- PREPARATION AND REACTIONS OF CYCLOPENTADIENYLDICARBONYLIRON
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Although , (Fp=η-C5H5Fe(CO)2) (I) is stable and characterizable, the lower homologue FpCH2CH(CO2CH3)2 (II) is not; this we attribute to a facile elimination reaction resulting from the reactively acidic β-hydrogen of II.Formation of I from Fp- and XCH2CE2CH3 (X=Br, Cl; E=CO2CH2CH3) and cleavage of its Fe-C bonds (using H+, Br2, CeIV and HgII) occur without major amounts of ester group migrations, even though CH2CE2CH3 radicals are involved in some of these reactions.
- Chatnam, Peggy E.,Karp, Gary M.,Kaufman, Michael J.,Nyitray, William,Kerber, Robert C.
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p. 257 - 266
(2007/10/02)
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