Awesome and Easy Science Experiments about (1S,2S)-Cyclohexane-1,2-diamine

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A mono methylether Salen-type ligand, SalenMe-H (1) is prepared in a one flask reaction by condensation of trans-1,2-diaminocyclohexane with 2-methoxybenzenaldehyde and followed by the addition of 2,4-di-tert- butylsalicylaldehyde. Further reaction of 1 with Mg(OBn)2 in THF produces a magnesium alkoxide, [(SalenMe)Mg(OBn)]2 (2). Compound 1 reacts with ZnEt2 yields monomeric complex (SalenMe)ZnEt (3), which further reacts with 1 molar equiv of benzyl alcohol giving [(SalenMe)Zn(OBn)] 2 (4). Experimental results show that complexes 2 and 4 efficiently initiate the ring-opening polymerization of l-lactide and rac-lactide in a controlled fashion, yielding polymers with very low polydispersity indexes. Kinetic studies show a second-order dependency on [LA] and a first-order on [2] with magnesium complex 2 as an initiator. While zinc complex 4 is used as an initiator, the polymerization rate has a first order dependency on both [LA] and [4].

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Chiral Catalysts,
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Discovery of (1S,2S)-Cyclohexane-1,2-diamine

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Suitable derivatives of the four isomeric pentanoates have been structurally characterized in the solid and the gas phase. For the latter, the volatile ethyl esters of valeric, isovaleric, methylbutyric, and pivalic acid were investigated by a combination of molecular beam Fourier transform microwave (MB-FTMW) spectroscopy and theoretical calculations. Crystalline salts rather than esters were formed by reaction between the carboxylic acids and trans-1,2-diaminocyclohexane. For both gaseous and crystalline methylbutyrates, an essentially perpendicular arrangement of carboxylate and methyl group was observed; earlier structure determinations documented in the data base agree with this result. Two competing conformers of favourable energy were relevant for the corresponding isovalerates: They were associated with torsion angles around 20 and 50 between the carboxylate and the alkyl chain. Good agreements in conformation have also been achieved for our experimentally observed unbranched valerate derivatives and fully branched pivalates in solid and gas phase. Despite the apparent simplicity of the pentanoates, the identification of their lowest energy conformers represents a challenge for different methods and levels of theory.

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Can You Really Do Chemisty Experiments About (1S,2S)-Cyclohexane-1,2-diamine

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A three-component reaction between diamines (diaminobenzenes, diaminocyclohexanes, and piperazines), triethyl orthoformate, and diethyl phosphite was studied in some detail. In the case of 1,3- and 1,4-diamines and piperazines, products of the substitution of two amino moieties?the corresponding tetraphosphonic acids?were obtained. In the cases of 1,2-diaminobenzene, 1,2-diaminocyclohexanes and 1,2-diaminocyclohexenes, only one amino group reacted. This is most likely the result of the formation of hydrogen bonding between the phosphonate oxygen and a hydrogen of the adjacent amino group, which caused a decrease in the reactivity of the amino group. Most of the obtained compounds inhibited the proliferation of RAW 264.7 macrophages, PC-3 human prostate cancer cells, and MCF-7 human breast cancer cells, with 1, trans-7, and 16 showing broad nonspecific activity, which makes these compounds especially interesting in the context of anti-osteolytic treatment and the blocking of interactions and mutual activation of osteoclasts and tumor metastatic cells. These compounds exhibit similar activity to zoledronic acid and higher activity than incadronic acid, which were used as controls. However, studies of sheep with induced osteoporosis carried out with compound trans-7 did not support this assumption.

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Chiral Catalysts,
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Properties and Exciting Facts About 21436-03-3

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Compounds represented by general formula (I) below wherein R¹ and R², which are the same or different, each represent a hydrogen atom or a protective group for a hydroxyl group;, R³ represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5?C25-aliphatic hydrocarbon group which may be substituted with an aro­matic group, or a group of formula where R4 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5?C25-­aliphatic hydrocarbon group which may be sub­stituted with an aromatic group, and, R5 represents a hydrogen atom, or a saturated or unsaturated, linear, branched or cyclic, monovalent hydrocarbon group which may be substituted with an aromatic group; Q represents (a) a group of formula -X¹-A-Y¹-,where A represents a saturated or unsaturated, linear, branched or cyclic divalent C2?C16-­aliphatic hydrocarbon group which may be sub­stituted with an aromatic group, a divalent aromatic hydrocarbon group or a divalent aro­matic heterocyclic group;, one of X¹ and Y¹ represents and the other represents -O-, -S- or in which R6 and R7 each represent a hydrogen atom or a lower alkyl group; (b) a group of formula -X²-(CH2)l-Y²-,where one of X² and Y² represents a group of formula and the other represents -O-, -S- or represents a 4?7-­membered, divalent nitrogen-containing aromatic heterocyclic group, and R6 has the same meaning as defined above, and l is 0, 1 or 2; or (c) a group of formula where m is 2 or 3;, n is an integer of from 1 to 4. The compounds have excellent inhibitory activ­ity against acyl Co A-cholesterol-acyltransferase.

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Chiral Catalysts,
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Awesome and Easy Science Experiments about 21436-03-3

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An organocatalyzed endo [4+2] cycloaddition between enones as pro-diene and allylidene malononitrile as dienophile leading to cyclohexanones with two 1,3-related stereogenic centres and an all-carbon quaternary centre has been developed. The reactions were performed under ?green reaction? conditions using water as the reaction medium and ambient conditions. When allylidene cyanoacetate was used as the dienophile, cyclohexanones with three contiguous stereogenic centres, one of which is an all-carbon quaternary centre, were formed. The products were obtained in high yield and with acceptable diastereo- and enantioselectivity.

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Chiral Catalysts,
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New explortion of 21436-03-3

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The cleavage of DeltaDelta[Rh(th4,5ppy)2(mu-C1)]2 [th4,5ppy is enantiomerically pure (8R,10R)-2-(2?-thienyl)-4,5-pinenopyridine(-)] by 5 different diimines and 11 diamines yields monomeric cations Delta[Rh(th4,5ppy)2(N?N)]+. In all cases, the cleavage reaction preserves the original Delta configuration at the metal center. When N?N is a chiral or a prochiral ligand, various degrees of stereoselectivity is observed, depending on where the stereogenic center is located in N?N. The reported results open up a systematic method towards the synthesis of tris(bidentate)RhIII complexes with a completely predetermined stereochemistry.

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Chiral Catalysts,
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Some scientific research about (1S,2S)-Cyclohexane-1,2-diamine

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A series of N,P-ligands has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts for enantioselective allylic alkylation and olefin hydrogenation, respectively.

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Chiral Catalysts,
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Final Thoughts on Chemistry for (1S,2S)-Cyclohexane-1,2-diamine

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A Ni(NTf2)2 and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrate, which was the dinuclear chiral Ni complex. From information regarding the structure of the complex, the substrate was distorted to form a helical shape, and the carbon atoms involved in bond formation were close to each other. In addition, mechanistic studies revealed that the configuration of the olefin moiety was isomerized before bond formation.

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Chiral Catalysts,
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Some scientific research about (1S,2S)-Cyclohexane-1,2-diamine

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The deuterium isotope effects on the 13C chemical shifts and the electronic structure of the molecules, were analyzed. It was observed that the nuclear magnetic shielding depends on the vibrationally and rotationally averaged bond lengths and bond angles. The prerequisite for observing separate signals for the H- and the D species was to have slow exchange on the NMR time scale. Results show that the largest effects occurred in the bond in which the subsituted atom was directly involved.

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Chiral Catalysts,
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The Absolute Best Science Experiment for (1S,2S)-Cyclohexane-1,2-diamine

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Synthesis and properties of new imines and bisimines derived from 2-phenyl-1H-imidazole-4-carbaldehyde and amines/diamines were studied. (2-Phenyl-1H-imidazole-4-yl)methanol was oxidized to 2-phenyl-1H-imidazole-4- carbaldehyde with better yield 55% by the modification of literature procedure. This aldehyde was condensed with the following achiral and chiral amines or 1,2-diamines: ethanamine, propan-1-amine, butan-1-amine, 2-methylpropan-1-amine, cyclohexanamine, (2R)- and (2S)-3-methylbutan-2-amine, (1R)- and (1S)-1-cyclohexylethanamine, (S)-1-aminopropan-2-ol, (S)-1-(2-phenyl-1H- imidazol-4-yl)ethanamine, (S)-1-(2-phenyl-1H-imidazol-4-yl)-2-methylpropan-1- amine, (S)-1-(2-phenyl-1H-imidazol-4-yl)-3-methylbutan-1-amine, ethane-1,2-diamine, and (1R,2R)- and (1S,2S)-cyclohexane-1,2-diamine. Sixteen condensation products, especially chiral imines and bisimines, were prepared by founded procedures in 45-99% of yields and characterized by the 1H NMR spectroscopy in solution, mass spectrometry, and elemental analyses. The optical rotation values in the case of chiral ones were also observed. Stability constants of Cu(II) complexes of selected prepared imines/bisimines were determined.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare