3187-82-4Relevant articles and documents
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
Cívicos, José F.,Coimbra, Juliana S. M.,Costa, Paulo R. R.
, p. 3998 - 4006 (2017/08/29)
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.
Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols
Tsygankov, Alexey A.,Chun, Man-Seog,Samoylova, Alexandra D.,Kwon, Seongyeon,Kreschenova, Yuliya M.,Kim, Suhyeon,Shin, Euijin,Oh, Jinho,Strelkova, Tatyana V.,Kolesov, Valerii S.,Zubkov, Fedor I.,Semenov, Sergei E.,Fedyanin, Ivan V.,Chusov, Denis
supporting information, p. 615 - 619 (2017/03/11)
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.
Synthesis and crystal structure of a chiral lactam and three amino alcohols as potential protein tyrosine phosphates 1B inhibitors
?zhan Kocakaya, ?afak,Karakaplan, Mehmet,Scopelliti, Rosario
, p. 1342 - 1349 (2017/10/13)
Chiral lactam 2 and three chiral β-amino alcohols 3–5 have been synthesized and characterized by spectroscopic techniques. Regioselective ring opening reaction of chiral styrene oxide by an amine nucleophile was confirmed by X-ray diffraction data. Ligand 2–4 crystallizes in the tetragonal, orthorhombic and tetragonal crystal lattice system respectively. Ligands 2–6 have been used as potential inhibitors for protein tyrosine phosphatase 1B enzyme (PTP1B). The potential inhibitor effect of these molecules to the target protein was investigated by Dock and molecular dynamics calculations. Dock score analysis and Lipinski parameters suggested that ligands 1, 2, 4–6 are potential inhibitors towards PTP1B, thus indicating that the residues Arg24, Arg254 and Met258, Asp29 in the second active site of PTP1B are essential for the high selectivity of inhibitors. The results indicate that the polar hydrogen bonding interacts with Asp29, Gln102, and the amino acid residues of PTP1B are responsible for governing inhibitory potency of ligands 1–6.
Preparations of Saturated N-P-N Type Secondary Phosphine Oxides and their Applications in Cross-Coupling Reactions
Chang, Yu-Chang,Liang, Ya-Han,Hong, Fung-E
, p. 353 - 367 (2016/05/09)
A series of cyclohexane-1,2-diamine (3a-3d) and benzene-1,2-diamine derivatives (3e-3h) were pre- pared. Followed by hydrolysis, the reaction of 3a-3c with PCl3 successfully led to the formation of cor- responding metastable saturated heteroato
Zinc Acetate-Catalyzed Enantioselective Hydrosilylation of Ketones
Szewczyk, Marcin,Stanek, Filip,Bez?ada, Agata,Mlynarski, Jacek
supporting information, p. 3727 - 3731 (2016/01/25)
Zinc acetate complexes with a chiral diphenylethylenediamine (DPEDA)-derived ligand have been proved to be efficient catalysts for the enantioselective hydrosilylation of aryl ketones. Replacing pyrophoric dialkylzinc with the readily available zinc salt simplifies the procedures and provides excellent conversions (up to >99%) and enantioselectivities (ees up to 97%).
H2 CHX dedpa and H4 CHX octapa-Chiral acyclic chelating ligands for 67/68Ga and 111In radiopharmaceuticals
Ramogida, Caterina F.,Cawthray, Jacqueline F.,Boros, Eszter,Ferreira, Cara L.,Patrick, Brian O.,Adam, Michael J.,Orvig, Chris
, p. 2017 - 2031 (2015/06/09)
The chiral acyclic ligands H2CHXdedpa (N4O2), H2CHXdedpa-bb (N4O2), and H4CHXoctapa (N4O4) (CHX = cyclohexyl/cyclohexane, H2dedpa = 1,2-[[6-carbo
Crystal structure of a hybrid salt-cocrystal and its resolution by preferential crystallization: ((±)trans-N,N′- dibenzyldiaminocyclohexane)(2,3-dichlorophenylacetic acid)4
Mahieux, Julien,Gonella, Silvia,Sanselme, Morgane,Coquerel, Gerard
experimental part, p. 103 - 111 (2012/03/09)
trans-N,N′-Dibenzyldiaminocyclohexane (B) crystallizes with 2,3-dichlorophenylacetic acid (AH); the crystal structure, resolved by using crystal X-ray diffraction, revealed an odd stoichiometry composed of H 2B2+, two A- a
Asymmetric allylation reactions of aromatic aldehydes with allyltrichlorosilane catalyzed by chiral bisformamide-type organocatalysts
Tanimura, Yuya,Ishimaru, Kaori
experimental part, p. 345 - 349 (2012/07/14)
Asymmetric allylation reactions of aromatic aldehydes with allyltrichlorosilane were catalyzed by C2-symmetrical chiral bisformamides in the presence of potassium carbonate and potassium phosphate, to afford the corresponding homoallylic alcoho
Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols
Aral, Tarik,Karakaplan, Mehmet,Hosgoeren, Halil
experimental part, p. 794 - 802 (2012/08/28)
A series of novel chiral β-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1, 2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of β-blockers and structurally complex molecules.
Reversible aminal formation: Controlling the evaporation of bioactive volatiles by dynamic combinatorial/covalent chemistry
Buchsnee Levrand, Barbara,Godin, Guillaume,Trachsel, Alain,De Saint Laumer, Jean-Yves,Lehn, Jean-Marie,Herrmann, Andreas
, p. 681 - 695 (2011/03/22)
Dynamic mixtures generated by reversible aminal formation efficiently prolong the duration of evaporation of bioactive volatile aldehydes. Secondary diamines used for the generation of dynamic mixtures are obtained by treatment of primary diamines with carbonyl compounds and reduction of the diimines with NaBH4. The reversibilities of the reactions were demonstrated by NMR measurements in buffered aqueous solutions. Kinetic rate constants and equilibrium constants for the formation and hydrolysis of aminals were determined. The performance of dynamic mixtures as delivery systems for perfumery ingredients was tested after deposition onto cotton, and the long-lastingness of fragrance evaporation was investigated by dynamic headspace analysis against a reference sample. The simplicity of the concept together with its excellent performance makes this delivery system highly interesting for applied perfumery. Reversible aminal formation might also be successfully applicable to dynamic combinatorial/covalent chemistry for screening of pharmaceutically or catalytically active ligands and receptors. The evaporation of bioactive volatiles that are emitted from flowers to attract insects and that are used as fragrances in our everyday life is limited in time. Dynamic mixtures obtained by reversible aminal formation of suitably designed diamines with volatile aldehydes prolong the perception of these compounds in functional perfumery.
