Extracurricular laboratory:new discovery of (1S,2S)-Cyclohexane-1,2-diamine

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21436-03-3, Name is (1S,2S)-Cyclohexane-1,2-diamine, molecular formula is C6H14N2, belongs to chiral-catalyst compound, is a common compound. In a patnet, once mentioned the new application about 21436-03-3, Quality Control of: (1S,2S)-Cyclohexane-1,2-diamine

The isothermal and isochoric crystallizations of (±)-trans-1,2- diaminocyclohexane, C6H10(NH2)2, (±)-DACH, yield enantiomeric conglomerates of orthorhombic symmetry, space group P21212, the same as obtained by isobaric crystallization. Despite the compression to 73% of ambient pressure volume, no racemic compound of DACH was formed. This contradicts for this compound the possibility of reverse causality between density and preferred enantiomorphic/racemic crystallization in Wallach’s rule. The crystal structures have been determined at 0.36, 0.52, 0.65, 1.19 and 2.04 GPa at 296 K by single-crystal X-ray diffraction. It has been established that the enantiomeric-conglomerate crystallization of DACH at ambient pressure is mainly due to the molecular arrangement, governed by the close-packing rule in the crystal. High pressure enhances the close packing, and it does not change the course of crystallization of (±)-DACH. The shortest intermolecular contacts, NH…N and CH…N, become most compressed between 0.36 and 2.04 GPa, indicating that such weak hydrogen bonds are enhanced by pressure. The phase diagram of (±)-DACH has been outlined to 2.04 GPa. The Royal Society of Chemistry 2011.

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.21436-03-3, Name is (1S,2S)-Cyclohexane-1,2-diamine, molecular formula is C6H14N2. In a Article,once mentioned of 21436-03-3, category: chiral-catalyst

The previous literature demonstrates that donor atoms softer than oxygen are effective for separating trivalent lanthanides (Ln(III)) from trivalent actinides (An(III)) (Nash, K.L., in: Gschneider, K.A. Jr., et al. (eds.) Handbook on the Physics and Chemistry of Rare Earths, vol. 18-Lanthanides/ Actinides Chemistry, pp. 197-238. Elsevier Science, Amsterdam, 1994). It has also been shown that ligands that “restrict” their donor groups in a favorable geometry, appropriate to the steric demands of the cation, have an increased binding affinity. A series of tetradentate nitrogen containing ligands have been synthesized with increased steric “limits”. The pK a values for these ligands have been determined using potentiometric titration methods and the formation of the colored copper(II) complex has been used as a method to determine ligand partitioning between the organic and aqueous phases. The results for the 2-methylpyridyl-substituted amine ligands are encouraging, but the results for the 2-methylpyridyl-substituted diimines indicate that these ligands are unsuitable for implementation in a solvent extraction system due to hydrolysis. Springer Science+Business Media, LLC 2012.

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A series of homogeneous and heterogenized gold metal complexes show high activity and selectivity for the homo-coupling of a large variety of aryl boronic acids, being of general utility for the synthesis of C 2-symmetric biaryls. The Royal Society of Chemistry 2005.

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.21436-03-3, Name is (1S,2S)-Cyclohexane-1,2-diamine, molecular formula is C6H14N2. In a Patent,once mentioned of 21436-03-3, Quality Control of: (1S,2S)-Cyclohexane-1,2-diamine

The present invention relates to novel, non-peptidic small organic compounds having an affinity for cyclophilin (CyP)-type immunophilin proteins. In the compounds of this invention, at least two carbo- or heterocyclic groups are attached to a central saturated, partially saturated, or aromatic 5-6 membered carbocyclic ring by a combination of straight or branched linker chains. The invention further relates to pharmaceutical compositions comprising one or more of the said compounds, and to the uses of these compounds and compositions for binding CyP-type proteins, inhibiting their peptidyl-prolyl isomerase activity, and for research, development, and therapeutic applications in a variety of medical disorders, such as neurological disorders, hair loss disorders, ischemic disorders, and disorders caused by viral or protozoan infection.

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Reaction of chiral phosphorodiamidites with trimethylsilyltriflate affords chiral phophorus(III) triflate species, such as 1-trifluoromethylsulfonato-2,9-(dibenzyl)diaza-1-phospha[4.0.3]bicyclononane 4, which has been examined by a combination of solution and solid state analytical techniques. Arguably the most important feature of this molecule is the nature of the interaction between phosphorus and triflate oxygen atoms. Single crystal X-ray diffraction analysis reveals that the phosphorus atom interacts principally with two oxygen atoms from two different triflate groups in the solid state, implying overall four-coordination at phosphorus. At distances of 2.841 and 2.755 A, these interactions are well within the van der Waals distance for a phosphorus-oxygen [P-O] interaction (ca. 3.35 A) but are nevertheless over 1 A longer than expected for a single [P-O] covalent bond. Investigations in solution via a combination of 31P, 19F, 13C, variable concentration, variable temperature NMR spectroscopy and solution conductivity provide support for a phosphorus-oxygen interaction which is intermediate between ‘ionic’ (two-coordinate phosphorus) and ‘covalent’ (three-coordinate phosphorus) and which possesses dynamic character in solution. Indeed, it has proved possible to calculate a relative equilibrium constant between ‘ionic’ and ‘covalent’ forms of 4 using empirical NMR data (13C and 19F; CH2Cl2 solvent; 300 K). These calculations return an equilibrium constant of ca. 3 (2.8 using 13C-NMR data and 3.3 using 19F-NMR data) in favour of the ionic form, a result commensurate with those suggested from variable temperature 19F-NMR and solution conductivity studies. Indeed, that the triflate group in 4 is capable of being displaced readily has been demonstrated by reaction with two-electron nitrogen, oxygen and phosphorus donor molecules. We have found 13C{1H}-NMR spectroscopy to be an extremely valuable probe of the ionic character of the triflate group in such systems providing a quantitative measure of the relative strength of interaction (relative basicity Br) between donor molecule and phosphorus atom of 4; the stronger the interaction, the more ionic the character of the triflate group and the lower the value of Br. Indeed, Br values for various ligands correlate well with steric and electronic properties of the latter and 31P-NMR resonances of the adducts themselves. As expected, the relative basicity of a given ligand correlates to the equilibrium constants K for adduct formation, which range from 39 M-1 for the weakest binding ligand studied (1,4-dioxane) to 5.4×104 M-1 for the strongest binding ligand (4-Me2N-NC5H4).

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The construction of new and efficient chiral TADF materials with red emission and the exploration of their applications in OLED devices still remain a great challenge for the difficulty in molecular design and low efficiency of devices. In this work, we synthesized a couple of 1,8-naphthalimide-based enantiomers (?)-(R,R)-CAI-DMAC and (+)-(S,S)-CAI-DMAC. The enantiomers not only exhibit high thermal stability with decomposition temperature of 405 C, excellent electrochemical properties, and good thermally activated delayed fluorescence (TADF) properties with small DeltaEST of 0.07 eV, but also show obvious mirror-image circular dichroism and circularly polarized luminescence properties. Moreover, by using (?)-(R,R)-CAI-DMAC and (+)-(S,S)-CAI-DMAC as emitters, the OLEDs with the bands both centred at 592 nm achieved high maximum external quantum efficiency of 12.4% and 12.3%, respectively.

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In this work, we investigate the potential of separating mixtures of the guest solvents aniline (ANI), N-methylaniline (NMA) and N,N-dimethylaniline (DMA) by means of host?guest chemistry principles employing two novel host compounds, namely trans-N,N?-bis(9-phenyl-9-xanthenyl)cyclohexane-1,2-diamine (1,2-DAX) and trans-N,N?-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,2-diamine (1,2-DAT). These aniline solvents may exist in such mixtures since NMA and DMA are often prepared from ANI by alkylation methods, and reaction yields are seldom quantitative. Owing to their similar boiling points, ranging from 184 to 196 ºC, the more usual distillation techniques for their separation are challenging. After recrystallization experiments of the two host compounds from various combinations of these anilines, it was revealed that host?guest chemistry certainly has the potential to serve as an alternative separation strategy for such mixtures. Equimolar ANI/DMA solutions proved most successful, where both 1,2-DAX and 1,2-DAT showed near-quantitative selectivity for DMA (90%). Both single crystal diffraction and thermal analyses were employed in order to understand the preferential behaviour displayed by each host compound.

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An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions gamma-nitro-beta-aryl-alpha-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABAB receptor agonist baclofen.

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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 21436-03-3, Name is (1S,2S)-Cyclohexane-1,2-diamine, molecular formula is C6H14N2. In a Article,once mentioned of 21436-03-3, Formula: C6H14N2

A doubly stereocontrolled organocatalytic asymmetric Michael addition to the synthesis of substituted succinimides is described. Starting from aldehydes and maleimides, both enantiomers of the succinimides could be obtained in high to excellent yields (up to 98%) and enantioselectivities (up to 99%) when one of the two special chiral diterpene-derived bifunctional thioureas was individually used as a catalyst. Moreover, these catalysts can be efficiently used in large-scale catalytic synthesis with the same level of yield and enantioselectivity.

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New chiral manganese complexes of N4 ligands derived from 2-acetylpyridine were prepared and used as catalysts in the enantioselective epoxidation of olefins, using H2O2 as an oxidant to give epoxides, with excellent conversions (up to 99%) and enantiomeric excess (up to 88%) within 1 h at 0C. A detailed mechanistic study was undertaken based on the information obtained by single crystal X-ray, optical rotation, UV-Vis, CD spectra and kinetic studies, and revealed that the reaction is first order with respect to the concentration of catalyst and oxidant and independent of substrate concentration. The complex (0.1 mol%) was successfully subjected to recyclability experiments over 3 cycles in the epoxidation of styrene with H2O2 as an oxidant and acetic acid as an additive at 0C with retention of performance.

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Chiral Catalysts,
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