3187-83-5

Upstream product

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane tartrate 
• 694-83-7 rac-diaminocyclohexane 
• 4383-05-5 2-hydroxy-3-methoxybenzyl alcohol 
• 32044-22-7 (1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate 
• 110-83-8 cyclohexene 

Downstream Products

• 193824-05-4 (1R,2R)-N,N’-di(2-hydroxybenzyl)-1,2-diaminocyclohexane 
• 133603-96-0 C₂₀H₂₄N₂O₂ 
• 249931-84-8 N-(2-hydroxylbenzaldehyde)-1-amino-2-cyclohexaneimine 
• 1537890-05-3 (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxyphenyl)-methylphosphonic acid] 
• 1537890-09-7 tetraisopropyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxyphenyl)methylphosphonate] 
• 1537890-07-5 tetraethyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxyphenyl)methylphosphonate] 
• 1537890-04-2 tetramethyl (R,R)-1,2-cyclohexylenediamino-di-(R,R)-[(2-hydroxyphenyl)methylphosphonate] 

Relevant academic research and scientific papers

Stereoselective protonation of 2-methyl-1-tetralone lithium enolate catalyzed by salan-type diamines

Asymmetric protonation of ketone enolates is a convenient alternative to asymmetric alkylation of enolates that allows to convert racemic ketones into their optically active form. Here, we have reported an efficient enantioselective protonation of 2-methyl-1-tetralone lithium enolate catalyzed by salan-type diamines. A broad series of salan-type catalysts were synthesized, including several previously unknown, and subsequently tested in the title reaction. For the first time, a chiral amine used as organocatalyst has shown better results than as stoichiometric protonating agent. Application of only 10 mol% of salan allows to obtain the title ketone with high yield and enantiomeric excess up to 75%. The DFT calculations of the structure of the catalyst and its complex with lithium enolate were conducted, which makes it possible to propose a likely reaction mechanism.

Synthesis, Characterization, and in Vitro Cytotoxicity of Platinum(II) Complexes Bearing Chiral Tetradentate Salicylaldimine Ligands

A series of platinum(II) complexes with chiral Schiff base ligands derived from various salicylaldehydes with (R,R′)- and (S,S′)-cyclohexanediamine were synthesized and characterized by ESI-MS, IR, and NMR. Obtained spectra with typical signals were in agreement with suggested molecular formulae of the complexes. Their photophysical properties were studied by UV-visible and emission spectroscopies. The UV-Vis showed the typical band with low energy at visible range 400-500 nm for MLCT, and this band can emit the luminescent band with emission maximum wavelengths at 529-595 nm. The in vitro cytotoxicity of obtained platinum(II) complexes was screened for KB and MCF-7 human cancer cell lines. The results showed that (S)-enantiomers were more active than (R)-enantiomers and the different positions of methoxy group in salicyl ring gave different cytotoxicities.

Polymerization of Ethylene in the Presence of Titanium(IV), Zirconium(IV), and Vanadium(V) Coordination Compounds with Salen Ligands

Abstract: Coordination compounds of titanium(IV), zirconium(IV), and vanadium(V) with chiral salen ligands have been obtained and characterized, and their catalytic activity in the polymerization reaction of ethylene has been studied. It has been shown that in the presence of polymethylaluminoxane as a cocatalyst, the activity of the titanium-containing catalyst system reaches 944 kgPE mol(Ti)?1 h?1 and leads to the preparation of ultrahigh-molecular-weight polyethylene.

Efficient conversion of CO2into cyclic carbonates at room temperature catalyzed by Al-salen and imidazolium hydrogen carbonate ionic liquids

A novel process for the efficient synthesis of cyclic carbonates from CO2 and epoxides at room temperature in the absence of a solvent has been achieved by using Al-salen complexes as catalysts and imidazolium hydrogen carbonate ionic liquids ([CnCmIm][HCO3]) as cocatalysts. As a halide ion-free cocatalyst, [CnCmIm][HCO3] showed higher catalytic reactivity compared to traditional halogen-containing quaternary ammonium salts (such as (nBu)4NBr) and organic bases. The catalytic system can be used for the cycloaddition of a series of substrates with good to excellent yields at room temperature in the absence of a solvent. Besides, the catalytic system can be easily recycled at least four times without significant loss of catalytic activity. A possible mechanism was proposed, in which Al-salen and carbene activate the epoxides and CO2 respectively.

Stabilized Ru[(H2O)6]3+ in Confined Spaces (MOFs and Zeolites) Catalyzes the Imination of Primary Alcohols under Atmospheric Conditions with Wide Scope

Imines are ubiquitous intermediates in organic synthesis, and the metal-mediated imination of alcohols is one of the most direct and simple methods for their synthesis. However, reported protocols lack compatibility with many other functional groups since basic supports/media, pure oxygen atmospheres, and/or released hydrogen gas are required during reaction. Here we show that, in contrast to previous metal-catalyzed methods, hexa-aqueous Ru(III) catalyzes the imination of primary alcohols with very wide functional group tolerance, at slightly acid pH and under low oxygen atmospheres. The inorganic metal complex can be supported and stabilized, integrally, within either faujasite-type zeolites (Y and X) or a metal organic framework (MOF), to give a reusable heterogeneous catalyst which provides an industrially viable process well below the flammability limit of alcohols and amines.

Solvent-Free Synthesis of Salen Ligands and Pd(II)- and Cu(II)-Salen Complexes: Their Use in the Oxidation of α-Tetralones to α-Naphthols

Racemic trans -cyclohexane-1,2-diamine was allowed to react with eleven aldehydes with different patterns of substitution at the aromatic ring, in the absence of solvent, by manually milling the reagents. The corresponding imines were obtained in moderated to high chemical yields, in only 10 minutes of reaction. A one-pot, two-step preparation of stable complexes of selected imines with Pd(OAc) 2 and Cu(OAc) 2 and the use of these complexes as catalysts in the aromatization of methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate to the corresponding methyl 1-hydroxynaphthalene-2-carboxylates, is also reported.

Chiral and non-conjugated fluorescent salen ligands: AIE, anion probes, chiral recognition of unprotected amino acids, and cell imaging applications

Natural products are usually non-conjugated and chiral, but organic luminescent materials are commonly polycyclic aromatic molecules with extended π-conjugation. In the present work, we combine with the advantages of non-conjugation and chirality to prepare a series of novel and simple salen ligands (41 samples), which have a non-conjugated and chiral (S,S) and (R,R) cyclohexane or 1,2-diphenylethane bridge but display strong blue, green, and red aggregation-induced emission (AIE) with large Stokes shifts (up to 186 nm) and high fluorescence quantum yields (up to 0.35). Through hydrogen and halogen bonds, these flexible salen ligands can be used as universal anion probes and chiral receptors of unprotected amino acids (enantiomeric selectivity up to 0.11) with fluorescence quantum yields up to 0.29 and 0.27, respectively. Moreover, the effects of different chiral bridges on the molecule arrangement, AIE, and anion and chiral recognition properties are also explored, which provide unequivocal insights for the design of non-conjugated chiral and soft fluorescent materials.

Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols

A series of N,N′-dialkylated derivatives of (1R,2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of α-hydroxy γ-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein-Ponndorf-Verley reductions and Henry reactions.

Efficient and diastereoselective synthesis of bis-quinazolinedione derivatives via low-valent titanium reagent

An efficient and simple method for the synthesis of chiral benzo[5,6][1,3]oxazino[4,3-c]quinoxalinedione and octahydroquinoxalino-[1,2-c:4,3-c′]diquinazolinedione derivatives using 2-hydroxybenzaldehydes (or 2-nitrobenzaldehydes) and chiral cyclohexane-1,2-diamine as the starting materials promoted by low-valent titanium reagent has been described. The structures of all synthesized products were identified by their IR, 1H NMR, 13C NMR and HRMS analysis, and the structure of compound 8b was confirmed by X-ray diffraction analysis.

Salen(Co(III)) imprisoned within pores of a metal-organic framework by post-synthetic modification and its asymmetric catalysis for CO2 fixation at room temperature

Herein, a new preparation strategy of chiral metal-organic frameworks (CMOFs) has been demonstrated. By adsorption and then post-synthetically modified (PSM) procedures, chiral salen(Co(iii)) could be imprisoned within the cages of an MOF and remained in its free form. This is the first report on the successful application of CMOFs in heterogeneous asymmetric catalysis for coupling CO2 with epoxides to obtain optically active cyclic carbonates at room temperature.