cas 21436-03-3, (1S,2S)-(+)-1,2-Diaminocyclohexane

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In vivo studies of a platinum(II) metallointercalator
An in vivo study for determining the toxicity and efficacy of [Pt(S,S-dach)(phen)Cl2·1.5H2O·0.5HCl (PHENSS) in female Specific Pathogen Free (SPF) Swiss nude mice bearing PC3 tumour xenografts revealed PHENSS to be non-toxic and effective in decreasing tumour growth. The Royal Society of Chemistry.
Fisher, Dianne M.,Fenton, Ronald R.,Aldrich-Wright, Janice R.
p. 5613 - 5615
(2008)
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Thermochemical and Structural Studies of New Chiral and Achiral Long Alkyl Chain Functionalized Imidazolinium Ionic Liquids
Adding to the versatile class of ionic liquids (ILs), an entirely new series of imidazolinium-based ionic liquids is reported herein, offering chirality and important thermal characteristics, such as polymorphism, glass transition, and plastic crystalline behavior. An efficient and general procedure for the preparation of long N,N′-alkyl chain-substituted compounds with either saturated (s) or chiral (c) cyclohexyl (cyC6)-substituted imidazolium (Im) backbones, namely, [C12C12RsIm][A] (A = Br-, [BF4]-, [ClO4]-, [PF6]- R = H, Me, iPr) and [C12C12cIm-cyC6][A] (A = Br-, I-, [I3]-, [BF4]-, [ClO4]-, [PF6]-, [SbF6]-, [BPh4]-), was developed, and the novel compounds were studied by thermochemical methods (DSC, TGA), X-ray diffraction in the small angle regime (SAXS), single-crystal X-ray diffraction (SC-XRD), and specific rotation analysis.
Seidl, Vera,Sternberg, Michelle,Heinemann, Frank W.,Schmiele, Martin,Unruh, Tobias,Wasserscheid, Peter,Meyer, Karsten
p. 6276 - 6288
(2021/10/20)

“Backdoor Induction” of Chirality: Trans-1,2-cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts
This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer-coordination sphere, well-defined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β-dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.
Glasovac, Zoran,Kirin, Sre?ko I.,Kokan, Zoran,Opa?ak, Sa?a,Peri?, Berislav
p. 2115 - 2128
(2019/01/04)

Using enantioselective dispersive liquid–liquid microextraction for the microseparation of trans-cyclohexane-1,2-diamine enantiomers
A new chiral separation system effective for the enantioselective extraction of racemic trans-cyclohexane-1,2-diamine is presented. Enantioselective dispersive liquid–liquid microextraction has been used for the chiral microseparation of trans-cyclohexane-1,2-diamine, with a chiral azophenolic crown ether being identified as a versatile chiral selector. The influence of various process conditions on the extraction performance was studied experimentally. It was found that the operational selectivity in one extraction step is mainly related to the type and volume of the solvents, chiral selector concentration, extraction time, temperature of sample solution, and pH. At optimum conditions (300?μL of diethyl ether as the extraction solvent 1?mL of methanol as the disperser solvent, with 5?mmol?L?1 chiral selector concentration, pH of the sample equal to 4.5, 30?min extraction time and a temperature of 10?°C), the distribution ratio of (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine was 18.3 and 1.8, respectively, while the enantioselectivity value of 10.2 was found at the optimum condition.
Hashemi, Majid,Hadjmohammadi, Mohammad Reza
p. 454 - 459
(2017/03/23)

Method for synthesizing trans-cyclohexyldiamine
The invention discloses a method for synthesizing trans-cyclohexyldiamine. The method comprises the following steps: by using epoxy cyclohexane as the raw material, carrying out ring opening with ammonia water, adding sulfuric acid for dewatering and salification, adding free alkali, carrying out ring opening with ammonia water, and distilling to obtain the trans-cyclohexyldiamine. The method has the advantages of high repetitiveness of the synthesis route, and simple and accessible raw materials, and provides an alternative scheme for obtaining the trans-cyclohexyldiamine pure product.
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(2017/08/29)

Preparation of C 2-Symmetric Biaryl Bisiminium Salts and Their Use as Organocatalysts for Asymmetric Epoxidation
Two C 2-symmetric bisiminium salt species containing biphenylazepinium units and derived from two chiral diamines were prepared and tested as organocatalysts for asymmetric epoxidation.
Bulman Page, Philip C.,Farah, Mohamed M.,Buckley, Benjamin R.,Chan, Yohan,Blacker, A. John
p. 126 - 130
(2015/12/26)

METHOD OF PRODUCING OPTICALLY ACTIVE TRANS-1,2-DIAMINOCYCLOHEXANE
A method produces optically active trans-1,2-diaminocyclohexane, in which a crystal of optically active trans-1,2-diaminocyclohexane is obtained by crystallization from a solution of optically active trans-1,2-diaminocyclohexane. Optically active trans-1,2-diaminocyclohexane with high purity is obtained in a favorable yield from a solution of optically active trans-1,2-diaminocyclohexane. The optically active trans-1,2-diaminocyclohexane with high purity is useful as a raw material for a large number of medicines.
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Paragraph 0057

(2016/02/28)

The iron(II) complex [Fe(CF3SO3)2(mcp)] as a convenient, readily available catalyst for the selective oxidation of methylenic sites in alkanes
The efficient and selective oxidation of secondary C-H sites of alkanes is achieved by using low catalyst loadings of a non-expensive, readily available iron catalyst [Fe(II)(CF3SO3)2(mcp)], {Fe-mcp, [mcp=N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)cyclohexane-trans-1,2-diamine]}, and hydrogen peroxide (H2O2) as oxidant, via a simple reaction protocol. Natural products are selectively oxidized and isolated in synthetically amenable yields. The easy access to large quantities of the catalyst and the simplicity of the C-H oxidation procedure make this system a particularly convenient tool to carry out alkane C-H oxidation reactions on the preparative scale, and in short reaction times.
Canta, Merce,Font, David,Gomez, Laura,Ribas, Xavi,Costas, Miquel
p. 818 - 830
(2014/04/03)

Efficient chiral resolution of (±)-cyclohexane-1,2-diamine
A novel and efficient method has been developed for the chiral resolution and separation from cis-cyclohexane-1,2-diamine of (±)-cyclohexane-1,2- diamine, which reacts with xylaric acid, a substitute for tartaric acid. This method provides (1R,2R)-cyclohexane-1,2-diamine, and (1S,2S)-cyclohexane-1,2- diamine and cis-cyclohexane-1,2-diamine in good yield with high optical purity.
Gao, Chuan-Zhu,Wang, Tian-Shuai,Chen, Jia,Fei, Fan,Zhang, Yan,Yang, Bo
p. 490 - 492
(2014/11/08)

Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas
A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.
Lalonde, Mathieu P.,McGowan, Meredeth A.,Rajapaksa, Naomi S.,Jacobsen, Eric N.
supporting information
p. 1891 - 1894
(2013/04/10)

Mechanism of living lactide polymerization by dinuclear indium catalysts and its impact on isoselectivity
A family of racemic and enantiopure indium complexes 1-11 bearing bulky chiral diaminoaryloxy ligands, H(NNOR), were synthesized and fully characterized. Investigation of both the mono- and the bis-alkoxy-bridged complexes [(NNOR)InX]2[μ-Y][μ-OEt] (5, R = tBu, X = Y = Cl; 8, R = Me, X = I, Y = OEt) by variable temperature, 2D NOESY, and PGSE NMR spectroscopy confirmed dinuclear structures in solution analogous to those obtained by single-crystal X-ray crystallography. The dinuclear complexes in the family were highly active catalysts for the ring-opening polymerization (ROP) of lactide (LA) to form poly(lactic acid) (PLA) at room temperature. In particular, complex 5 showed living polymerization behavior over a large molecular weight range. A detailed investigation of catalyst stereoselectivity showed that, although (R,R/R,R)-5 is highly selective for l-LA, only atactic PLA is obtained in the polymerization of racemic LA. No such selectivity was observed for complex 8. Importantly, the selectivities obtained for the ROP of racemic LA with (R,R/R,R)-5 and (R,R/R,R)-8 are different and, along with kinetics investigations, suggest a dinuclear propagating species for these complexes.
Yu, Insun,Acosta-Ramirez, Alberto,Mehrkhodavandi, Parisa
supporting information; experimental part
p. 12758 - 12773
(2012/09/05)

Synthesis and characterization of cobalt(iii) cyanide complexes: Cobalt participation in the decomposition of radical anion of TCNQ
Reaction of Co(CH3COO)2·4H2O, KTCNQ (TCNQ = 7,7,8,8-tetracyanoquinodimethane) with the racemic or chiral H 2salency (N,N′-bis(salicylidene)-1,2-cyclohexanediamine) ligand afforded three Co(iii) complexes K[Co(salency)(CN)2]·CH 3OH (1), K[Co(S,S-salency)(CN)2]·H2O (1S) and K[Co(R,R-salency)(CN)2]·CH3OH (1R), which have been fully characterized. The cyanide groups in these three complexes are generated from the in situ decomposition of the radical anion of TCNQ with the participation of cobalt(ii). Single-crystal X-ray diffraction analysis reveals that complex 1 exhibits an infinite double stair-like chain structure. However, the chiral complexes 1S and 1R show chain structures consisting of two independent sub-chains. All of these chains are bridged by the K+ ions, with the cyanides interacting with K+ in the end-on and unusual side-on π-type mode. Second-order nonlinear optical effect studies in the solid state revealed that 1S and 1R are SHG active. The Royal Society of Chemistry.
Tan, Chun-Hong,Ma, Xiao,Zhu, Qi-Long,Huang, Yi-Hui,Wen, Yue-Hong,Hu, Sheng-Min,Sheng, Tian-Lu,Wu, Xin-Tao
p. 8708 - 8713
(2013/02/23)

METHOD FOR FRACTIONATING STEREOISOMERIC COMPOUNDS
The present invention relates to a method for fractionating stereoisomeric compounds which have at least one alcohol and/or amino group.
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(2009/02/11)

A new approach to enantiomerically pure bis-imidazoles derived from trans-1,2-diaminocyclohexane
Racemic as well as enantiomerically pure trans-1,1′-(cyclohexane-1,2-diyl)bis(imidazole N-oxides) were prepared from trans-cyclohexane-1,2-bis(methylidenamine) and 1,2-dione monooximes (α-hydroxyiminoketones). The enantiomeric purity of selected products was determined by means of 1H NMR spectroscopy in the presence of (+)-(R)-(tert-butyl)(phenyl)phosphonothioic acid as a chiral solvating agent. Deoxygenation by treatment with Raney-nickel led to the corresponding chiral bis-imidazoles.
Mucha, Paulina,Mloston, Grzegorz,Jasinski, Marcin,Linden, Anthony,Heimgartner, Heinz
p. 1600 - 1607
(2008/12/21)

Enantioselective analysis of an asymmetric reaction using a chiral fluorosensor
(Chemical Equation Presented) An axially chiral 1,8-dipyridylnaphthalene N,N′-dioxide has been employed in enantioselective fluorescence analysis of the enzymatic kinetic resolution of trans-1,2-diaminocyclohexane. The procedure eliminates cumbersome purification and derivatization steps required by traditional methods. The results demonstrate the potential of fluorescence spectroscopy using suitable chiral chemosensors for real-time analysis of the enantiomeric composition of chiral compounds and for high-throughput screening of asymmetric reactions.
Tumambac, Gilbert E.,Wolf, Christian
p. 4045 - 4048
(2007/10/03)

Improved resolution methods for (R,R)- and (S,S)-cyclohexane-1,2-diamine and (R)- and (S)-BINOL
Starting from inexpensive L-(+)-tartaric acid, it was possible to resolve and obtain pure both enantiomers of trans-cyclohexane-1,2-diamine 1 and thence both enantiomers of BINOL 2, two of the most powerful, chiral inducing backbones in asymmetric catalysis. The modified method is very economic, not only due to an almost doubling of the overall yields of enantiomerically pure compounds (86% 1, 83% 2) but also due to the easy recovery of resolving agent 1 [66% (R,R)-1, 79% (S,S)-1] in the BINOL resolution. An improvement in the yield of the preparation of racemic BINOL is also recorded.
Schanz, Hans-Joerg,Linseis, Michael A.,Gilheany, Declan G.
p. 2763 - 2769
(2007/10/03)

Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid
(S)-(+)-1-Amino-3-phenyloxy-2-propanol, (R)-(-)-2-amino-1-phenylethanol, (S)-(+)-1-amino-2-propanol, (1S,2S)-(+)-2-aminocyclohexanol and (1S,2S)-(+)-1,2-diaminocyclohexane were resolved using dehydroabietic acid. It was shown that good to high enantiomeric purity, between 81～>99% ee, was obtained and that dehydroabietic acid could be easily and efficiently recovered in a reusable form.
Guangyou, Zhang,Yuquing, Liao,Zhaohui, Wang,Nohira, Hiroyuki,Hirose, Takuji
p. 3297 - 3300
(2007/10/03)

Platinum (II) antitumor compounds
The present invention describes platinum (II) compounds and compositions useful for treating a subject with a tumor and/or inducing apoptosis in a population of cells. The present invention also describes pharmaceutical compositions containing the aforementioned inventive compound(s) in combination with a pharmaceutically acceptable carrier. Additionally, the invention further provides a method of inducing apoptosis in a population of cells and a method of treating a subject with a tumor, wherein the method comprises administering to the subject a therapeutically effective amount of the aforementioned compound(s) or composition(s).
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(2008/06/13)

The stereospecific addition of hydroxylamines to α,β-unsaturated sulfones, nitriles and nitro compounds
N-Alkyl hydroxylamines have been shown to undergo a highly stereospecific cis addition to α,β-unsaturated sulfones, nitriles and nitro compounds.
O'Neil, Ian A.,Cleator, Ed,Southern, J. Mike,Bickley, Jamie F.,Tapolczay, David J.
p. 8251 - 8254
(2007/10/03)

A diamine-exchange reaction of dihydropyrazines
Dihydropyrazines reacted with 1,2-diamines to form tetraazadecalins as intermediates, and then the reaction proceeded forward to dissociate into alternate dihydropyrazine and diamine, or backward to dissociate into the starting materials in certain equilibrium. The product distribution is controlled by diamine-exchange equilibrium reaction. The various equilibrium reactions were analyzed by NMR spectroscopy.
Yamaguchi, Tadatoshi,Ito, Shigeru,Iwase, Yukiko,Watanabe, Kenji,Harano, Kazunobu
p. 1677 - 1680
(2007/10/03)

An efficient method for opening nonactivated aziridines with TMS azide: Application in the synthesis of chiral 1,2-diaminocyclohexane
A variety of N-substituted aziridines have been opened with TMS azide in MeCN at rt in the absence of any Lewis acid. The reaction was extended to the synthesis of (R,R)- and (S,S)-1,2-diaminocyclohexane. (C) 2000 Elsevier Science Ltd.
Chandrasekhar,Sekar,Singh
p. 10079 - 10083
(2007/10/03)

Sequential biocatalytic resolution of (±)-trans-cyclohexane-1,2-diamine. Chemoenzymatic synthesis of an optically active polyamine
Candida antarctica lipase-catalysed double monoaminolysis of dimethyl malonate by (±)-trans-cyclohexane-1,2-diamine allows the sequential resolution of the latter compound, affording an enantiopure bis(amidoester), (R,R)-3, which is subsequently transformed into an optically active polyamine, (R,R)-9.
Alfonso, Ignacio,Astorga, Covadonga,Rebolledo, Francisca,Gotor, Vicente
p. 2471 - 2472
(2007/10/03)

Kinetic resolution of chiral auxiliaries with C2-symmetry by lipase-catalyzed alcoholysis and aminolysis
Three cyclic diols, 1,2-cyclohexanediol (1), 1,3-cyclohexanediol (2), and 1,3-cyclopentanediol (3), two acyclic unsaturated diols, 1,5-hexadiene-3,4-diol (4) and 1,7-octadiyne-3,6-diol (5), and a cyclic diamine, 1,2-cyclohexanediamine (6), have been kinetically resolved in alcoholysis and aminolysis reactions, catalyzed by Candida antarctica component B lipase, using S-ethyl thiooctanoate or ethyl octanoate as acyl donors. Acceptable stereoselectivity was achieved in most cases. Acta Chemica Scandinavica 1996.
Mattson, Anders,Orrenius, Christian,Oehrner, Niklas,Unelius, C. Rikard,Hult, Karl,Norin, Torbjoern
p. 918 - 921
(2007/10/03)

Diastereo- and enantioselective synthesis of vicinal diamines via aza-Michael addition to nitroalkenes
The asymmetric synthesis of protected 1,2-diamines 4 by aza-analogous Michael addition of (-)-(2S,3R,4R,5S)-1-amino-3,4-dimethoxy-2,5-bis(methoxymethyl)pyrrolid ine (ADMP) to nitroalkenes 1 in good overall yields and high enantiomeric excesses (ee = 93-96%) is described. The auxiliary constitutes a novel chiral equivalent of ammonia and is removed under reductive N-N bond cleavage with Raney nickel, which also reduces the nitro group. The absolute configuration was determined by NMR-spectroscopic methods and polarimetry.
Enders, Dieter,Wiedemann, Juergen
p. 1443 - 1450
(2007/10/03)

Process of synthesizing binaphthyl derivatives
A process of synthesizing a compound of the formula 1: STR1 is disclosed, which comprises reacting a compound of the formula 2: STR2 with diphenylphosphine in the presence of an amine base and a nickel catalyst to produce a compound of formula 1.
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(2008/06/13)

Optical resolution method
The present invention provides three optical resolution methods. The first aspect comprises the steps of adding an optically active bifunctional resolving reagent to a bifunctional compound to form a liquid material, precipitating crystals therefrom, and treating the crystals and the liquid material separately with an acidic material, a basic material, or a basic material and an acidic material, to obtain a pair of enantiomers of an optically active bifunctional compound. The second aspect comprises an optical resolution method by which one necessary enantiomer of a pair of enantiomers in an optically active bifunctional compound is exclusively obtained. The third aspect comprises a method for racemizing one unnecessary enantiomer of a pair of enantiomers in an optically active bifunctional compound which is formed by the optical resolution method of the present invention.
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(2008/06/13)

Water soluble platinum complexes of novel malonate derivatives
This disclosure describes water soluble platinum complexes of novel malonate derivatives which possess the property of inhibiting the growth of tumors in mammals.
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(2008/06/13)

Platinum complexes of aliphatic tricarboxylic acids
Platinum complexes of aliphatic tricarboxylic acids useful for inducing regression and/or palliation of cancer diseases in mammals.
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(2008/06/13)

Antineoplastic platinum (IV) complexes and compositions
New substantially isomerically pure tetrahalo (1,2-diaminocyclohexane) Pt (IV) complexes having antineoplastic activity are disclosed.
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(2008/06/13)

Synthesis of platinum (IV) antineoplastic agents
There is provided a method of synthesizing tetrachlorocyclohexanediammine platinum (IV) compounds in high purity and yield, the level of purity being suitable for pharmacological use. The compounds produced by this process have antineoplastic agents against tumor cells resistant to cis-platinum.
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(2008/06/13)

Process for optical resolution of crude trans-1,2-cyclohexanediamine
Crude trans-1,2-cyclohexanediamine (DACH) contained in a mixture of amines derived as a by-product from the manufacture of 1,6-hexanediamine (HDA) or any other synthesis process crude by-product stream may be directly resolved into its optical isomers by using a mixture of tartaric acid and a second acid selected from the group consisting of C1 to C8 carboxylic acids and HCl, without first separating the DACH in high purity from the mixed amine component by-product stream. Alternatively, racemic DACH may be separated from a crude mixed amine component by-product stream by use of oxalic, sulfuric and/or nitric acids. This racemic product may then be optically resolved by techniques known in the art.
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(2008/06/13)