Archives for Chemistry Experiments of 4254-15-3

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Chiral MOF incorporating chiral guests: Structural studies and enantiomer-dependent luminescent properties

Two new inclusion compounds of chiral guest molecules in chiral metal?organic framework (MOF) were obtained by soaking the crystalline [Zn2(dmf)(bdc)(S-lac)]·DMF (dmf = N,N-dimethylformamide; bdc = terephthalate; S-lac = S-lactate) in neat R-1,2-propanediol (R-pd) or S-1,2-propanediol (S-pd). Single crystal X-ray analysis for [Zn2(dmf)(bdc)(S-lac)]·R-pd (1) and [Zn2(S-pd)2(bdc)(S-lac)]·S-pd (2) showed that two enantiomers of the same alcohol react quite differently with the chiral porous framework, occupying different positions and form different types of interactions with the host. While the R-pd acts only as a guest molecule inside the channels, the S-pd coordinates to zinc cations of the framework and substitutes both guest and coordinated DMF of the original MOF. The chirality of 1,2-propanediol guest molecules has a considerable effect on luminescent properties of the [Zn2(dmf)(bdc)(S-lac)] host. The luminescence spectra of [Zn2(S-pd)2(bdc)(S-lac)]·S-pd and the original [Zn2(dmf)(bdc)(S-lac)]·DMF are almost identical while the luminescence spectra of [Zn2(dmf)(bdc)(S-lac)]·R-pd features new peak, compared with the original host. Also, the incorporation of alcohol guest molecules has different impact on quantum yields of the luminescence of the host, depending on the chirality of the isomer. In a more general prospect, such enantiomer-dependent luminescent properties of [Zn2(dmf)(bdc)(S-lac)] represent a chiral luminescence sensing, which is quite an extraordinary and rare phenomenon for chiral MOFs.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Discovery of 24621-61-2

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Absolute stereochemistry of amphidinolide C.

[structure in text] The absolute configurations at 12 chiral centers in amphidinolide C (1), a potent cytotoxic 25-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were determined to be 3S, 4R, 6R, 7R, 8R, 12R, 13S, 16S, 20R, 23R, 24R, and 29S by combination of NMR analyses, degradation experiments, and synthesis of the C-1-C-7 segment.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Mixed neutral compounds of palladium(II) and platinum (II) chelated by diolato(2-) and di-imine ligands

The synthesis and characterization are described for compounds abbreviated (a) 1-5: [Pd(phen)(OO)], where OO = the dianion from 1,2-ethanediol (1), (+)-1,2-propanediol (2), (±)-2,3-butanediol (3), (-)-1,2-butanediol (4), catechol (5); (b) the sulphur analogue (6) [Pd(phen)(SCH2CH2S)], from ethane-1,2-dithiol; (c) the platinum analogue (7) [Pt(phen)(OCH2CH2O)]; (d) the 2,2?-bipyridyl analogue (8), [Pd(bipy)(OCH2CH2O)] (phen = 1,10-phenanthroline and bipy = 2,2?-bipyridyl).

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Final Thoughts on Chemistry for C17H14O

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Sulfamic acid: An efficient, cost-effective and green catalyst for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free

Aromatic aldehydes undergo crossed-aldol condensation with ketones in the presence of catalytic amount of sulfamic acid (SA) to afford the corresponding alpha, beta-unsaturated aldol products under solvent-free conditions in good to high yields at 45-80 C.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The Absolute Best Science Experiment for C4H10O2

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This type of reactivity has quickly become one of the cornerstones of modern catalysis .In a patent, Computed Properties of C4H10O2, name is (2S,3S)-Butane-2,3-diol, belongs to chiral-oxygen-ligands compound, introducing its new discovery. Computed Properties of C4H10O2

Production of (2S,3S)-2,3-butanediol and (3S)-acetoin from glucose using resting cells of Klebsiella pneumonia and Bacillus subtilis

Production of highly pure (2S,3S)-2,3-butanediol ((2S,3S)-2,3-BD) and (3S)-acetoin ((3S)-AC) in high concentrations is desirable but difficult to achieve. In the present study, glucose was first transformed to a mixture of (2S,3S)-2,3-BD and meso-2,3-BD by resting cells of Klebsiella pneumoniae CICC 10011, followed by biocatalytic resolution of the mixture by resting cells of Bacillus subtilis 168. meso-2,3-BD was transformed to (3S)-AC, leaving (2S,3S)-2,3-BD in the reaction medium. Using this approach, 12.5gl-1 (2S,3S)-2,3-BD and 56.7gl-1 (3S)-AC were produced. Stereoisomeric purity of (2S,3S)-2,3-BD and enantiomeric excess of (3S)-AC was 96.9 and 96.2%, respectively.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Extended knowledge of C17H14O

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The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. An article , which mentions Computed Properties of C17H14O, molecular formula is C17H14O. The compound – 1,5-Diphenylpenta-1,4-dien-3-one played an important role in people’s production and life., Computed Properties of C17H14O

Deprotection of oximes, phenylhydrazones, semicarbazones and thiosemicarbazones to the corresponding carbonyl compounds using cetyltrimethylammonium peroxodisulfate as a new and selective oxidizing agent

Cetyltrimethylammonium peroxodisulfate (CTA)2S2O 8 was quantitatively prepared and used for the deprotection of oximes, phenylhydrazones, semicarbazones and thiosemicarbazones to the corresponding carbonyl compounds in acetonitrile. Its agent is more efficient and has advantages over similar reagents in terms of the amount of oxidant, short reaction time, simple work up, and high yield.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Brief introduction of (2S,3S)-Butane-2,3-diol

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Tetrahydrofuran antifungals

A compound represented by the formula I STR1 wherein X is independently both F or both Cl or one X is independently F and the other is independently Cl; R1 is a straight or branched chain (C3 to C8) alkyl group substituted by one or two phosphate ester groups (e.g., a phosphate ester convertible in vivo into a hydroxy group) thereof or a pharmaceutically acceptable salt thereof and pharmaceutical compositions thereof useful for treating and/or preventing fungal infections are disclosed.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Final Thoughts on Chemistry for (2S,3S)-Butane-2,3-diol

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Enantiomeric recognition of amino acid salts by macrocyclic crown ethers derived from enantiomerically pure 1,8,9,16-tetrahydroxytetraphenylenes

Asymmetric synthesis of (R,R)- and (S,S)-1,8,9,16- tetrahydroxytetraphenylenes was achieved from starting material (2R,3R)-butane-2,3-diol and (2S,3S)-butane-2,3-diol respectively by utilizing a center-to-axis strategy. A series of crown ether compounds 20, 24, and 25 and their corresponding enantiomers derived from chiral tetrahydroxytetraphenylene were synthesized in enantiomerically pure forms. Enantiomeric recognition properties of these hosts toward l- and d-amino acid methyl ester hydrochloride were studied by the UV spectroscopy titration. The tetramer hosts (S,S,S,S,S,S,S,S)-20 and (R,R,R,R,R,R,R,R)-20 exhibited the best enantioselectivities toward l- and d-alanine methyl ester hydrochloride salt with KL/KD = 4.1 and KD/KL = 3.9, respectively. The new chiral macrocyclic hosts would further enrich the host-guest chemistry.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

More research is needed about 1,5-Diphenylpenta-1,4-dien-3-one

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Gem-Dimethyl-cyclo-propanation of dibenzyl-ideneacetone using triisopropyl sulfoxonium tetra-fluoro-borate

The reaction between dibenzyl-ideneacetone (dba) and tri-isopropyl sulfoxonium tetra-fluoro-borate has been reinvestigated. The stereochemistry of the major diasteromeric bis-(gem-dimethyl-cyclo-propane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenyl-cyclo-prop-yl][(1SR,3SR)-2,2- dimethyl-3-phenyl-cyclo-prop-yl]methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two ml-ecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclo-propanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The mol-ecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis-(dimethyl-cyclo-prop-yl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclo-propanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis-(dimethyl-cyclo-prop-yl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Modellreaktionen zur Umsetzung von Ferrocen-1,1′-dithiol mit Diolefinen:II. Die Saeuren- und Basenkatalysierten Reaktionen von Ferrocenthiolen mit aktivierten Olefinen

Both ferrocenethiol and ferrocene-1,1′-dithiol, Fe(C5H5)(C5H4SH) and Fe(C5H4SH)2, add to activated olefins to give 1:1 and 1:2 adducts, respectively.The base-catalysed (NEt3) reactions of the monofunctional ferrocenethiol with the mono-olefins methyl methacrylate, methyl vinyl sulfone and benzylidene acetone lead to expected 1:1 adducts whereas 2:1 adducts are obtained with bifunctional olefins such as divinyl sulfone and dibenzylidene acetone.The corresponding bifunctional ferrocene-1,1′-dithiol gives 1:2 adducts with methyl methacrylate, methyl vinyl ketone and benzylidene acetone.For comparison, the aliphatic 2-ferrocenyl-ethanethiol, Fe(C5H5)(C5H4-CH2CH2SH), was reacted with methyl vinyl sulfone and divinyl sulfone.In all cases, the disulfides Fc-SS-Fc and Fc-CH2CH2-SS-CH2CH2-Fc, respectively, are also formed.The acid-catalysed (HCl) reactions of ferrocenethiol and ferrocene-1,1′-dithiol, Fe(C5H5)(C5H4SH) and Fe(C5H4SH)2, with isobutyl vinyl ether produce the expected 1:1 and 1:2 adducts although the formation of dimercaptals is also possible.Thus the reaction of ferrocene-1,1′-dithiol with isobutyl vinyl ether leads to both the 1:2 adduct and the 2-methyl 1,3-dithia-<3>ferrocenophane, Fe(C5H4S)2CH(CH3), and the HCl-catalysed addition of ferrocenethiol to 1,4-butadienol divinyl ether gives 1,1-di(ferrocenylmercapto) ethane, CH3CH(SFc)2.The new sulfur derivatives of ferrocene were characterized by 1H and 13C NMR spectroscopy.Keywords: Iron; Ferrocene; Ferrocene thiol; Addition to olefins; NMR

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate