cas 69703-25-9, N,N'-DIBENZYL-1,4,10,13-TETRAOXA-7,16-DIAZACYCLOOCTADECANE

Articles about 69703-25-9Total 19 be found

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Specific Cation-transport Abilities of New Macrocyclic Polyamine Compounds
The lipophilic macrocyclic polyamine carriers (1) and (2) mediated efficient ammonium-cation transport with characteristic properties not observed in previously reported crown ether systems.
Tsukube, Hiroshi
p. 970 - 971
(1983)
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Characteristic Transport Properties of Diaza-crown Ethers for Primary and Secondary Ammonium Cations
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Tsukube, Hiroshi
p. 2685 - 2686
(1984)
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Selective mono-alkylation of N-methoxybenzamides
We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.
Chen, Zenghua,Hu, Le'an,Zeng, Fanyun,Zhu, Ranran,Zheng, Shasha,Yu, Qingzhen,Huang, Jianhui
supporting information
p. 4258 - 4261
(2017/04/21)

Improved Syntheses of Benzyl Hydraphile Synthetic Cation-Conducting Channels
The tris(macrocycle)s that function in bilayer membranes as ion channels have recently shown versatile new applications such as antibiotic synergists and as agents for direct injection chemotherapy. This report records the development of new and versatile approaches to these molecules that produce significantly better overall yields for a group of previously reported hydraphiles having spacer chains ranging from octylene to hexadecylene.
Curvey, Nichole S.,Luderer, Sarah E.,Walker, John K.,Gokel, George W.
p. 2771 - 2779
(2015/02/19)

The syntheses and structural characterizations of some monoaza- and diaza-crown ethers
Several aza-crown ethers have been synthesized and their structures determined by X-ray crystallography. In a modified synthesis of diaza-18-crown-6 we isolated two of the intermediates, viz. the NaI salt (1) of N,N′-dibenzyldiaza-18-crown-6 and the salt-free macrocycle (2), and determined their stuctures. In compound (1) a hydrated crown-encapsulated sodium cation was revealed with both benzyl groups folded down and away from the water molecule while in compound (2) a centrosymmetric crown with the benzyl groups splayed out from the ring was found. In addition, we have determined the X-ray crystal structures of monoaza-18-crown-6 and the hydrochloride salt of monoaza-15-crown-5. In the former, the crown resides on an inversion centre showing N/O disorder, and in the latter the protonated amine hydrogen bonds with the chloride anion. CSIRO 1999.
Fewings, Kym R.
p. 1109 - 1114
(2007/10/03)

Synthetic models for transmembrane channels: Structural variations that alter cation flux
Twelve novel bis- or tris(macrocyclic) compounds have been designed as models for cation-conducting channels that function in phospholipid bilayer vesicle membranes. In general, the channel model systems have the structure "sidearm-crown-spacer-crown-spac
Murillo, Oscar,Watanabe, Shigeru,Nakano, Akio,Gokel, George W.
p. 7665 - 7679
(2007/10/03)

Synthesis and Spectral Properties of New Fluorescent Probes for Potassium
Studies on the preparation and properties of two new, selective fluorescent probes CD18, 1 and C18, 2 for potassium are described.The probes incorporate the 1,10-diaza-18-crown-6 chelating group for the ion and the coumarin group as the fluorophore.The probes are compared with the known reagent PBFI.C18 shows considerably greater selectivity for potassium over sodium than PBFI.
Crossley, Roger,Goolamali, Zia,Gosper, Jeffrey J.,Sammes, Peter G.
p. 513 - 520
(2007/10/02)

KINETIC AND EQUILIBRIUM STUDIES OF THE REACTION OF 1,3,5-TRINITROBENZENE WITH CRYPTANDS IN ACETONITRILE
Kinetic and equilibrium data for the formation of the adduct from 1,3,5-trinitrobenzene (TNB) with cryptands (221, 222, 21, 22 and di-(Ph-CH2)22) in acetonitrile are reported.The influence of structure and pKa of cryptands on the rate constants, activation and reaction parameters are discussed.A reaction mechanism between TNB and different cryptands has been proposed.
Leska, Boguslawa,Hes, Marzanna,Schroeder, G.
p. 671 - 680
(2007/10/02)

Syntheses of unsymmetrically N,N′-bis (substituted)-4,13-diaza-18-crown-6-ether derivatives as a new electron donor-spacer-acceptor triad
A simple and general synthetic strategy potentially applicable for the preparation of a wide variety of unsymmetrically N,N′-bis(substituted)-4, 13-diaza-18-crown-6-ether derivatives was reported.
Morimoto, Minoru,Fukui, Keijiro,Kawasaki, Norioki,Iyoda, Tomokazu,Shimidzu, Takeo
p. 95 - 98
(2007/10/02)

4,13-Diaza-18-crown-6
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Gatto, Vincent J.,Miller, Steven R.,Gokel, George W.
p. 227 - 227
(2017/05/06)

PYRIDINO-ARMED DIAZA-CROWN ETHERS FOR SPECIFIC TRANSPORT OF "TRANSITION METAL CATIONS"
A new series of double armed diaza-crown ethers, bearing pyridino- and quinolino-arm groups, were first shown to effectively bind and transport some "transition metal cations" via threedimensional complexations, which were not attained by common crown ethers.
Tsukube, Hiroshi,Yamashita, Kouichi,Iwachido, Tadashi,Zenki, Michio
p. 569 - 572
(2007/10/02)

N,N'-BIS(SUBSTITUTED)-4,13-DIAZA-18-CROWN-6 DERIVATIVES HAVING PI-DONOR-GROUP-SIDEARMS: CORRELATION OF THERMODINAMICS AND SOLID STATE STRUCTURES
Solution thermodynamic data and solid state structure information are used to show that a series of N,N'-bis(substituted)-4,13-diaza-18-crown-6 (BiBLE) derivatives which lack oxygen or nitrogen donor groups in the sidearms do not utilize the sidearms for binding but show considerable variation in their binding constants.
Arnold, Kristin A.,Viscariello, Anthony M.,Kim, MinSook,Gandour, Richard D.,Fronczek, Frank R.,Gokel, George W.
p. 3025 - 3028
(2007/10/02)

NOVEL SYNTHETIC ACCESS TO 15- AND 18-MEMBERED RING. DIAZA-BIBRACCHIAL LARIAT ETHERS (BiBLEs) AND A STUDY OF SIDEARM-MACRORING. COOPERATIVITY IN CATION BINDING
An extremely practical synthesis of 4,10-diaza-15-crown-5, 4,13-diaza-18-crown-6, and symmetrically N,N'-disubstituted derivatives thereof, is presented along with the first survey of cation binding data for the 15-membered ring systems.
Gatto, Vincent J.,Arnold, Kristin A.,Viscariello, Anthony M.,Miller, Steven R.,Gokel, George W.
p. 327 - 330
(2007/10/02)

Syntheses and Binding Properties of Bibracchial Lariat Ethers (BIBLEs): Survey of Synthetic Methods and Cation Selectivities
A new, two-step method for the synthesis of 4,10-diaza-15-crown-5 and 4,13-diaza-18-crown-6 and their N,N'-disubstituted derivatives from bis(secondary amines) and 1,2-bis(2-iodoethoxy)ethane is described.Essentially, the method utilizes the incipient sidearms as nitrogen-protecting groups prior to cyclization.The yields for cyclization are high, ranging from 32percent to 77percent.The N,N'-disubstituted derivatives of 4,10-diaza-15-crown-5 produced by alkylation or acylation (A), acylation followed by reduction (AR), cyclization (C), hydrogenolysis (H), or single-step cyclization (O) have the following sidearms: H (H, 91percent), MeOCH2CH2 (C, 38percent), EtOCOCH2 (A, 62percent), PhCH2 (C,72percent), 2-MeOPh (C, 52percent), 2-furanylmethyl (C, 67percent), and 2-nitrobenzyl (A, 50percent).N,N'-Dibenzyl-4,10-diaza-18-crown-6 was obtained by cyclization in 63percent yield.The N,N'-disubstituted derivatives of 4,13-diaza-18-crown-6 produced with the new method have the following sidearms: H (H, 92percent), CO-Et (A, 100percent), n-propyl (AR, 78percent), n-butyl (C, 77percent), n-hexyl (C, 32percent; A, 50percent; O, 7percent), n-octyl (AR, 45percent), CO-n-heptyl (A, 71percent), n-nonyl (O, 11percent;A, 45percent;AR, 39percent), CO-n-undecyl (A, 87percent), n-tetradecyl (AR, 26percent), CO-n-tridecyl (A, 78percent), n-hexadecyl (A, 25percent), n-octadecyl (AR, 60percent), CO-n-heptadecyl (A, 100percent), allyl (O, 26percent), propargyl (O, 22percent), HOCH2CH2 (O, 28percent), MeOCH2CH2 (C, 43percent; AR, 76percent), HOCOCH2 (hydrolysis, 81percent), EtOCOCH2 (A, 92percent), PhCH2 (O, 29percent;C, 66percent), 2-furanylmethyl (O, 27percent, C, 62percent), 2-hydroxybenzyl (A, 85percent), 2-methoxybenzyl (O, 30percent), 2-cyanobenzyl (A, 95percent), 2-nitrobenzyl (A, 90percent), 3-nitrobenzyl (A, 95percent), and 4-nitrobenzyl (A, 70percent).The new cyclization method is compared with other, previously published cyclization reactions with respect to overall yield and ease of purification.When this new cyclization cannot be used, diaza crown ethers can be prepared by alkylation of 4,10-diaza-15-crown-5 or 4,13-diaza-18-crown-6.The homogeneous equilibrium cation binding constants (log Ks) have been determined in anhydrous methanol solution for many of the compounds described herein with Na+, K+, and Ca+.The cation selectivities are rationalized in terms of polar, structural, and lipophilicity effects.
Gatto, Vincent J.,Arnold, Kristin A.,Viscariello, Anthony M.,Miller, Steven R.,Morgan, Charles R.,Gokel, George W.
p. 5373 - 5384
(2007/10/02)

Lipophilic Bis(monoaza crown ether) Derivatives: Synthesis and Cation-Complexing Properties
Eleven lipophilic bis(monoaza crown ether) derivatives were synthesized, in which two monoaza crown ethers with 9-, 12-, 15-, or 18-membered rings are linked through the nitrogen atoms by an alkane-, diether-, or diester-type bridge chain bearing a dodecyl group.Sodium and potassium binding with the bis(monoaza crown ether) was determined potentiometrically and compared with those for previous bis(crown ethers) 5 (n = 1 - 3) and corresponding monocyclic analogues 4 and 6 (n = 1 - 3).Marked bis(crown ether) effect was observed only for the alkane-type bis(monoaza-12-crown-4) and bis(monoaza-15-crown-5) derivatives 1 (n = 1,2) on complexing Na+ and K+, respectively.It was suggested that in some of the other bis(monoaza crown ethers) lariat-ether effect works instead.Bis(monoaza-9-crown-3) derivatives 1 and 2 (n = 0) possess very poor cation-complexing ability.Acidity constant values gave some hints about the bis(crown ether) effect.
Sakamoto, Hidefumi,Kimura, Keiichi,Koseki, Yasuaki,Matsuo, Mitsunori,Shono, Toshiyuki
p. 4974 - 4979
(2007/10/02)

Cation-binding Properties of New Armed Macrocyclic Host Molecules and Their Applications to Phase-transfer Reactions and Cation Membrane Transport
A new series of armed macrocyclic host molecules was prepared; the macrocycles were characterized by parent macrocyclic ligands and cation-ligating donor arms.Their cation-binding properties were significantly controlled by co-ordination characteristics od their parent macro-ring and donor sidearms, and chemical modifications of their basic structures provided interesting chemical functions.For example, a furan-bearing double armed crown ether showed high catalytic activity in some phase-transfer reactions; a multi-armed cyclam containing furan-oxygen atoms discriminated NH4(1+) ion from K(1+) and other related cations effectively.Such chemical functions of these armed macrocycles were not attained with common crown ethers and cryptands.Hence, further variations of ligand structures may lead to a new series of host molecules showing unique and important chemical functions.
Tsukube, Hiroshi,Takagi, Kentaro,Higashiyama, Tatsuo,Iwachido, Tadashi,Hayama, Naomi
p. 1033 - 1038
(2007/10/02)

Syntheses of Calcium-Selective, Substituted Diaza-Crown Ethers: A Novel, One-Step Formation of Bibracchial Lariat Ethers (BiBLEs)
Ten N,N-disubstituted derivatives of 4,13-diaza-18-crown-6 (7) have been prepared, three of which exhibit Ca2+, over either Na+ or K+, selectivity.This selectivity has been achieved by utilizing polar, yet uncharged, donor groups such as carbethoxymethyl.Several of these compunds have been prepared by a novel, one-step reaction of aliphatic primary amines with triethylene glycol diiodide.The compounds prepared by this method include examples having the following substituents on nitrogen: benzyl, 2-methoxybenzyl, 2-hydroxyethyl, allyl, 2-furylmethyl, and 2-pyridylmethyl.Isolated yields of pure product for the one-step reaction were in the range 26 +/- 4percent.The corresponding derivatives of 7 having 2-methoxyethyl, carbethoxymethyl, carboxymethyl, and 2-hydroxybenzyl sidearms were also prepared so that cation selectivity as a function of structure could be assessed.Homogeneous stability constants (Ks) for the association between the various ligands and Na+, K+, and Ca2+ were determined and are reported.Significant Ca2+ selectivity is achieved for the first time in these systems which should retain a high degree of binding dynamics since the donor groups of primary interest in this study are non-ionizable.
Gatto, Vincent J.,Gokel, George W.
p. 8240 - 8244
(2007/10/02)

'Double Armed' Crown Ethers with Specific Cation Transport Ability
Macrocyclic polyethers having two 'arms' available for cation binding provide new and characteristic transport abilities, based on their unique ligand topology, which were not attained in the usual crown ether and cryptand systems.
Tsukube, Hiroshi
p. 315 - 316
(2007/10/02)

Azethoxyl Nitroxide Spin-Labeled Crown Ethers and Cryptands with the N-O. Group Positioned near the Cavity
We report the synthesis and complexation properties of several nitroxide spin-labeled crown ethers and cryptands in which the N-O. group, in certain conformations, is thrust toward the cavity of the molecule.While initial approaches involving the cyclization of various unsymmetrically substituted tetraethylene glycols (e.g, 10, 11, and 15) were not promising, success was achieved by the sequential addition of substituted phenyl groups to nitrone 28, leading to nitroxide crown ethers 37 and 38.Nitroxide cryptand 60 was prepared by diacylation of diaza-18-crown-6 51 with azethoxyl nitroxide diacid chloride 57 followed by reduction.The ESR spectrum aN values of these nitroxides were not sensitive to the presence of K+, Na+, or Li+ in MeOH, While diaza-18-crown-6, decamethylene cryptand 55, and nitroxide cryptand 60 formed 1:1 complexes with NaBPh4 in CDCl3, nitroxide crown ethers 37 and 38 and amide 54 did not.Adaption of the quantitative methodology of Cram et al. showed that 55 and 60 bind Na+ somewhat better than dicyclohexyl-18-crown-6.K+ is bound better than Na+ by 55 and 60, tough not as strongly as dicyclohexyl-18-crown-6.The binding of K+ and Na+ by 37 and 38 is minimal.
Keana, John F. W.,Cuomo, John,Lex, Laszlo,Seyedrezai, Seyed E.
p. 2647 - 2654
(2007/10/02)