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

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To obtain a new anticancer drug, we focused on FER tyrosine kinase. Starting with high-throughput screening with our in-house chemical library, compound 1, which has a pyridine moiety, was found. Referring to their X-ray crystal structure with FES proto-oncogene tyrosine kinase, as a surrogate of FER followed by chemical modification including scaffold hopping of the pyridine template, we discovered pyrido-pyridazinone derivatives with potent FER kinase inhibitory activity. Here, we disclose the structure-activity relationship on the scaffold and representative compound 21 (DS21360717), which showed in vivo antitumor efficacy in a subcutaneous tumor model.

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Reference:
Chiral Catalysts,
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The one-pot reaction of (1S,2S)-(+)-1,2-diaminocyclohexane, 3-tert-butyl-2-hydroxybenzaldehyde and Zn(OAc)2·1.5H 2O in methanol under reflux gives the diastereoselective formation of the first zinc(II)-salen double helicate, P-(S, S)-1, which adopts a right-handed helicity. The stereochemistry of the helicates can be readily tuned through varying the chiral diamine backbone.

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Reference:
Chiral Catalysts,
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Development in the field of asymmetric catalysis is driven by the importance of stereochemically pure compounds in the field of pharmaceutical industry, agrochemicals and flavors. The unpredictable results given by new catalysts make the design of effective ones a long and costly work. Combinatorial asymmetric catalysis is efficient tools for finding best catalysts and it helps for many catalytic systems to be screened in a short period of time to decide about their effectiveness in synthesizing stereospicific products. This work describes rapid screening of chiral asymmetric oxazoline, imine, aminal and bisimine bidentate ligands and their in situ use for catalytic transfer hydrogenation of ketone in the presence of zinc. The ligands thus prepared in situ gave nearly same results with that of the purified version. The ligands which gave more than 70% ee with excellent conversions (?90%) were readily identified. Thus ligands with excellent results can be purified in bulk to save time and money.

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Chiral Catalysts,
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Besides the adducts from lithium amides to aromatic aldehydes, iminium salts, aminals, and N-silylimines of aromatic aldehydes are coupled by the black suspension obtained from TiCl4 and Mg turnings in tetrahydrofuran (THF).The 1,2-diarylethylenediamines with tertiary and primary amino groups thus obtained are formed with no or only moderate diastereoselectivity (products 4a-d (Scheme 2) and 5a-e (Scheme 3), respectively); the amine component may contain a strained ring or additional heteroatoms as in azetidin, bis(2-metoxyethyl)amine piperazine, morpholine, and thiomorpholine (products 6a-e; Table 1).By an in-situ procedure, ethylenediamines and propane-1,3-diamines with two secondary amino groups are cyclized with aromatic aldehydes to give exclusively trans-diaryl-substituted piperazine and perhydro-1,4-diazepine derivatives (products 7a-f; Table 2).Enantiomerically pure monocyclic trans,cis-5-alkyl-2,3-diaryl-piperazines and diazabicyclo<4.3.0>nonanes and –<4.4.0>decanes are obtained by employing suitable diamines prepared from the amino acids (S)-alanine, (S)-phenylalanine, (S)-proline, and from (S,S)- or (R,R)-cyclohexane-1,2-diamine, respectively (products 11a-i, 7e; Table 4).The configurations of all products are derived from the high-field NMR spectra, some of which are discussed in detail (Figs. 1 and 2, Tables 3 and 5); all new compounds are fully characterized by their physical data.Depending upon the structure of the components employed, the yields of purified products range from as low as 7percent to essentially quantitative.

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Chiral Catalysts,
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(E)1-acetyl-[2-(3-methyl-2-butenyloxy)benzylidene]indolin-2-one (1) gives competition between the intramolecular Hetero Diels-Alder (HDA) (thermal conditions) and the intramolecular ene reaction (IER) (magnesium perchlorate – MP – catalyzed conditions). Several complexes derived from MP and chiral bis-oxazolines were found to be excellent chemo- and enantioselective catalysts with a different degree of selectivity depending on the substituents on the oxazoline ring. The most chemoselective oxazolinic ligand forced the reaction to give a ratio of [HDA]:[[IER] products 5:95. The trans-(4,5-diphenyloxazoline)-MP complex is the best enantioselective catalyst and the product of the IER of 1 can be prepared in 75% yield and 88% e.e..

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Chiral Catalysts,
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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, Product Details of 21436-03-3

The left- and right-handed helical silica nanostructures were obtained with the aid of organic templates, the formation of the nanostructures might follow a co-operation self-assembly mechanism. The chirality of the organogel self-assemblies was successfully transcribed in to the silica. The helical pitch and pore size silica nanotubes sensitively depended on the optical purity of the neutral gelator in the reaction mixtures.

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Chiral Catalysts,
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Properties and Exciting Facts About (1S,2S)-Cyclohexane-1,2-diamine

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Compounds of formula (I) STR1where R 1 is hydrogen; R 2 is nitro, cyano or halo(lower)alkyl; R 3 is phenyl substituted with one or more substituents selected from halogen, cyano and lower alkoxy; A is a lower alkylene group; R 4 is a group CR 6 R 7 R 8 wherein R 6 and R 7 form, together with the carbon atom to which they are attached a cycloalkyl group optionally substituted with hydroxy, lower alkoxy or a lower alkanoylamino; and R 8 is hydrogen; its prodrug and a salt thereof.

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Chiral Catalysts,
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Asymmetric oxidation of sufides to sulfoxides by aqueous hydrogen peroxide with catalysis by titanium-salan complexes is presented. Optically active sulfoxides have been obtained with good to high enantioselectivities (up to 97% ee) by a tandem enantioselective oxidation and kinetic resolution procedure, the catalyst performing over 500 turnovers with no loss of enantioselectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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

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New substantially isomerically pure tetrahalo (1,2-diaminocyclohexane) Pt (IV) complexes having antineoplastic activity are disclosed.

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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 Patent,once mentioned of 21436-03-3, category: chiral-catalyst

The present invention is related to pure cis-diiodo-(trans-L-1,2-cyclohexanediamine) Pt (II) complex, and a process of its preparation. The present invention is further related to the preparation of oxaliplatin using said cis-diiodo-(trans-L-1,2-cyclohexanediamine) Pt (II) complex.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare