Asymmetric Synthesis and Crystal Structure of a Bioactive Morpholine Derivative

A novel morpholine derivative was synthesized by Michael addition/internal nucleophilic substitution of 4-（L）-menthyloxy（1R,2S,5R）-butenolide with phenyl-glyalcohol under mild condition, and its structure was determined by X-ray diffraction. The target compound belongs to orthorhombic, space group P212121 with a = 5.7729（7）, b = 11.5032（14）, c = 25.161（3）A, Mr = 319.35, Z = 4, V = 1670.8（4）A^3, Dc = 1.270 g/cm3, μ（MoKα） = 0.094 mm^-1, F（000） = 680, Flack = 0.01（2）, R = 0.0398 and wR = 0.0914.

An ionic 2D inorganic-organic hybrid of tris[((1H-tetrazol-5-yl)methyl)morpholine] dodecatungstophosphate(Ⅴ) pentahydrate:Synthesis X-ray crystal structure and spectroscopic characterizations

A unique ionic hybrid material[C_6H_(12)N_5O]_3[(PO_4)W__(12)O_(36)]·5H_2O has been synthesized from the reaction of((1H-tetrazole-5- yl)methyl)morpholine andα-H_3[(PO_4)W_(12)O_(36)]·21H_2O.It has successfully been characterized by elemental analysis,IR and ~1H NMR spectroscopies,TGA and single-crystal X-ray diffraction method.The title compound is constructed from the three [C_6H_(12)N_5O]^+ cations andα-Keggin[(PO_4)W_(12)O_(36)]^(3-) polyoxoanion.The most remarkable structural feature of this hybrid can...

Synthesis, Crystal Structure and Biological Activities of 2-(4-Fluorophenyl)-2-oxo-1-(1H-1,2,4-triazol-1-yl) ethyl morpholine-4-carbodithioate

The title compound, 2-（ 4-fluorophenyl ） -2-oxo-1-（ 1H-1, 2,4-triazol-1-yl ） ethyl morpholine-4-carbodithioate, was synthesized and its structure was confirmed by means of IR, MS, 1 H NMR and elemental analysis. The single crystal structure of the title compound was determined by X-ray diffraction. The preliminary biological test showed that the synthesized compound possesses some biological activities.

Dissociative Photoionization of Heterocyclic Molecule-Morpholine under VUV Synchrotron Radiation

The radiation damage of biomolecules, in particular with aliphatic compound, has been extensively studied. Morpholine is a typical six-membered aliphatic heterocyclic compound. In the present work, photoionization and dissociation of the morpholine monomer and subsequent fragmentations have been investigated by synchrotron vacuum ultraviolet photoionization mass spectrometry and theoretical calculations. The vertical ionization energy of morpholine monomer is 8.37±0.05 eV, which agrees reasonably well with a theoretical value 8.41 eV of morpholine. Experimentally observed fragmentation of morpholine (m/z=87 amu) gives rise to m/z=86 amu, m/z=57 amu, and m/z=29 amu. Based on experimental and theoretical results, it is found that the m/z=86 amu is produced by losing H atom, the m/z=57 amu is formed by the elimination of CH2O with a ring-opening process, the m/z=29 amu is generated by further dissociation of the fragment m/z=57 amu (C3H7N)+ by the elimination of C2H4. This finding would provide valuable insight into the photo-damage of aliphatic compounds, which may be related to living cells and other biological system.

Solid-phase Synthesis of-Haloaldehydes from Polymer-supported 4-(Phenylseleno)morpholine

Polystyrene-supported 4-(phenylseleno)morpholine was synthesized and could be used as an efficient ?selenenylating agent for saturated aldehydes. ?Haloaldehydes were prepared by reaction of polystyrene-supported ?selenoaldehydes with bromine or sulfuryl chloride in good yield and high purity.

Solid-phase Synthesis of Unsaturated β-Dicarbonyl Compounds from Polymer-supported 4-(Phenylseleno)morpholine

The solid-phase synthesis of unsaturated ?dicarbonyl compounds has been reported.

Tribological Behaviors of S,B-Containing Morpholine Derivatives as Additives in Rapeseed Oil

Two novel ashless and non-phosphorus S, B-containing morpholine derivatives, MBOC and MBOD, were prepared and their tribological behaviors in rapeseed oil （RSO） were evaluated using a four-ball tester. Thermal degradation tests were conducted to identify their thermal stabilities using a thermo-gravimetric analyzer. The worn surfaces of the steel balls were investigated by scanning electron microscopy （SEM）. The results indicated that the additives possessed high thermal stabilities and good load-carrying capacities. Moreover, they both had good anti-wear and friction reducing property at a relatively high concentration （1.5 m%） and under all test loads. The results of XPS analyses illustrated that the prepared compounds as additives in RSO could form a protective film containing inorganic sulfide, sulfate, oxidized compounds and organic nitrogen-containing compounds on the metal surface during the sliding process.

NON-ISOTHERMAL KINETICS OF THERMAL DECOMPOSITION OF A NOVEL ANTITUMOR AGENT 4-{5-[3,4-DIMETHYL-5-(3,4,5-TRIMETHOXYPHENYL)THIOPHEN-2-YL]-2-METHOXYPHENYL}MORPHOLINE

The thermal decomposition of a new antitumor agent,4-{5-[3,4-dimethyl-5-(3,4,5-trimethoxyphenyl)thiophen-2-yl]-2-methoxyphenyl}morpholine was studied by Differential Scanning Calorimetry(DSC)and Thermogravimetry(TG)/Derivative Thermogravimetry(DTG)methods at a flow rate of nitrogen gas of 120 mL/min,The kinetic parameters were obtained from the analysis of the corresponding curves by Kissinger's method,Ozawa's method and the integral method,The results indicate that the apparent activation energy and pre-exponential constants of the decomposition reaction are 106.67 kJ/mol and 10^6.19s^(-1),respectively.

Studies of Oxide Layers Grown at 260°C on A106 B Carbon Steel in Aqueous Medium with Ethanolamine or Morpholine

The water chemistry of the secondary coolant in the majority of Nuclear Power Plants is controlled by AVT (All Volatile Treatment), wherein volatile amines are used to maintain the alkaline pH required for minimizing the corrosion of structural materials which one of them is Carbon Steel. In this treatment, ammonia, morpholine and ethanolamine are commonly used as conditioning reagents. In this context, experiments were carried out by exposing carbon steel A106 B samples in a simulated secondary coolant in order to study the nature of the oxide films. The tests were performed in a static autoclave at 260°C using two media: I) hydrazine + morpholine and II) hydrazine + ethanolamine during different exposure periods up to ≈1020 h. The oxide film characterization was mainly studied using Scanning Electron Microscopy and X-ray diffraction. A chemical descaling procedure was used to obtain the material weight loss (W) of samples, the adherent and released oxide. The XRD analyses, for all exposures studied, showed that magnetite was the corrosion product formed in the films grown in both media. The material weight loss, after descaling, could be fitted by a law of the type W = ktn, up to 1020 h of exposure tested, resulting in n = 0.42, k = 6.24 for films grown in medium I) and n = 0.39, k = 6.08 for films grown in medium II) respectively (W is in mg/dm2 and t in h). The higher corrosion product release measured in the medium with morpholine could be important in power plant operation.

Utilizing morpholine for purely organic room temperature phosphors

In this article,morpholine,a non-conjugated heterocycle,is embedded intoπsystem to construct single-component organic room temperature phosphorescence(RTP)luminogens.The effect of morpholine on intermolecular interaction,crystal packing modes,and RTP performance is investigated systematically.The experimental and theoretical calculation results illustrate the versatility of morpholine in promoting the n-π*transition and intensifying the intermolecular interactions,which not only enhances the generation of triplet excitons,but also suppresses the nonradiative decay of triplet excitons.Impressively,TMPh containing three morpholine units shows an ultralong lifetime of 1.03 s and a visible afterglow up to 10 s.The unique dual delayed emission and long afterglow property allow potential application of morpholine derivatives in data encryption,and the time-dependent color change of afterglow emission is realized after removing the excitation source,providing a high-level data security.This article provides a new perspective for the design of purely organic RTP system without utilization of metal,or even any heavy atoms.

An Unexpected Discovery in the Willgerodt-Kindler Reaction of Acetophenone--the Formation of the 4-（Benzoylthiocarbonyl）morpholine

The Willgerodt-Kindler reaction of acetophenone was studied. Apart from the normal product 4-（benzylthiocarbonyl）morpholine, another product 4-（benzoylthiocarbonyl）morpholine was obtained unexpectedly. The structure of the latter was confirmed by 1R, IH NMR spectra and X-ray diffraction analysis. The mechanism of the reaction was discussed.

Morpholine Catalyzed One-pot Multicomponent Synthesis of Compounds Containing Chromene Core in Water

A series of dihydropyrano[c]chromene was obtained via condensation of aldehyde, malononitrile and 4-hydroxycoumarin in water catalyzed by morpholine, as a one-pot reaction. The significance of our findings relates to reducing the use of organic solvents, potentially toxic and hazardous materials, as well as its simplicity, good yields, mild conditions, and lower costs.

Morpholine triflate promoted one-pot,four-component synthesis of dihydropyrano[2,3-c]pyrazoles

A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate （MorT） to afford a series of dihydropyrano[2,3-c]pyrazoles, which were generally catalyzed by organic alkalis. Moderate to excellent yields, no chromatographic purification, and evasion of environmentally hazardous solvents in the reaction process make this protocol very useful for academia and industry.

Synthesis, Spectroscopic and Electrochemical Investigations of Two vic-Dioximes and Their Mononuclear Ni（Ⅱ）, Cu（Ⅱ） and Co（Ⅱ） Metal Complexes Containing Morpholine Group

Two vic-dioxime ligands （LxH2） containing morpholine group have been synthesized from 4-[2-（dimethylaminoethyl）] morpholine with anti-phenylchloroglyoxime or anti-monochloroglyoxime in absolute THF at -15 ℃. Reaction of two vic-dioxime ligands with MCl2·nH2O （M： Ni, Cu or Co and n=2 or 6） salts in 1 ： 2 molar ratio afforded metal complexes of type [M（LxH）2] or [M（LxH）2·2H2O]. All of metal complexes are non-electrolytes as shown by their molar conductivities （Am） in DMF （dimethyl formamide） at 10^-3 mol·L^-1. Structures of the ligands and metal complexes have been solved by elemental analyses, FT-IR, UV-Vis, ^1H NMR and ^13C NMR, magnetic susceptibility measurements, molar conductivity measurements. Furthermore, redox properties of the metal complexes were investigated by cyclic voltammetry.

Sulfonamide and Morpholine-Based Dual Chemosensor for Cu^2＋ and Ag^＋ in Different Solvent Media

The detection of cations has attracted considerable interest because of their importance in various physiological processes. In this study, compound 1 bearing sulfonamidc and morpholine functionalities was synthesized. Its structure was well characterized by NMR spectroscopy and mass spectrometry. UV/vis absorption spectra and fluorescence spectra indicated that it displayed high sensitivity and selectivity for Cu^2＋ and Ag^＋ by switching solvent media. It means that： （1） it showed selective response to Cu2＋ in acetonitrile, （2） whereas it exhibited high selectivity for Ag^＋ in water. The density functional theory calculations were used to clearly explain the different recognition behaviors in different solvent media. This research suggests that compound 1 bearing sulfonamide and morpholine functionalities could act as a multiftmctional chemosensor for monitoring multiple cations by changing solvent media and provides an alternative approach to design novel dual cations chemosensors.

Morpholine hydrazone scaffold： Synthesis, anticancer activity and docking studies

In this paper, synthesis and anticancer activities of morpholine hydrazones scaffold（1-17） thoroughly studied. Small series of morpholine hydrazones synthesized by treating 5-morpholinothiophene-2-carbaldehyde with different aryl hydrazides to form morpholine hydrazones scaffold（1-17）. The in vitro anticancer potential of all these compounds was checked against human cancer cell lines like Hep G2（human hepatocellular liver carcinoma） and MCF-7（human breast adenocarcinoma）. Analogs 13 had similar substantial cytotoxic effects towards Hep G2 with IC_（50） value 6.31±1.03μmmol/L when compared with the standard Doxorubicin（IC_（50）value 6.00±0.80μmmol/L）; while compounds 5,8 and 9 showed potent cytotoxicity against MCF-7 with IC_（50） value 7.08±0.42μmmol/L, 1.26±0.34μmmol/L and11.22±0.22μmmol/L respectively when compared with the standard Tamoxifen（IC_（50）= 11.00±0.40μmol/L）. Molecular docking studies also performed to understand the binding interaction.

Relative efficacy of some prokinetic drugs in morphine-induced gastrointestinal transit delay in mice

AIM:To study the relative efficacy of cisapride, metoclopramide,domperidone,erythromycin and mosapride on gastric emptying(GE)and small intestinal transit(SIT) in morphine treated mice. METHODS:Phenol red marker meal was employed to estimate GE and SIT in Swiss albino mice of either sex.The groups included were control,morphine 1 mg/kg(s.c.15 rain before test meal)alone or with(45 rain before test meal p.o.)cisapride 10 mg/kg,metoclopramide 20 mg/kg, domperidone 20 mg/kg,erythromycin 6 mg/kg and mosapride 20 mg/kg. RESULTS:Cisapride,metoclopramide and mosapride were effective in enhancing gastric emptying significantly(P<0.001) whereas other prokinetic agents failed to do so in normal mice.Metoclopramide completely reversed morphine induced delay in gastric emptying followed by mosapride. Metoclopramide alone was effective when given to normal mice in increasing the SIT.Cisapride,though it did not show any significant effect on SIT in normal mice,was able to reverse morphine induced delay in SIT significantly(P<0.001) followed by metoclopramide and mosapride. CONCLUSION:Metoclopramide and cisapride are most effective in reversing morphine-induced delay in gastric emptying and small intestinal transit in mice respectively.

Synthesis and structure characterization of novel calix[4](aza)crown derivatives

Three novel calix[4]（aza）crown deravatives have been synthesized, including a new [2]pseudorotaxane in which calix[4]- azacrown behaves as a stopper, a novel ＇tren＇ type calix[4]azacrown and a novel ＇spiro＇ type calix[4]azacrown containing moroholine unit. The structures of these compounds have been confirmed by NMR and MS.

Aminolysis of 1-(1-Hydroxybenzotriazolyl)-2,4-dinitrobenzene and 2-(1-Hydroxybenzotriazolyl)-5-nitropyridine

The reaction 1-(1-hydroxybenzotriazolyl)-2,4-dinitrobenzene 1 and 2-(1-hydroxybenzotriazolyl)-5-nitro-pyridine 2 with amines undergoes amination followed by elimination of the 1-hydroxyl benzotriazolyl anion. The kinetic data for the reaction of 1 and 2 with Mo, CHA and An in MeOH and AN proceeded by uncatalysed mechanism in which the rate limiting step is the leaving group departure, whereas the reaction with Mo in toluene proceeded by uncatalysed mechanism in which the formation of the zwitterionic intermediate is the rate determining step. While the reactions of 1 with CHA and An and the reaction of 2 with CHA in toluene proceeded by SB mechanism in which the rate determining step is the proton transfer process. The reactions of 1 and 2 with Mo in the three solvents and with CHA and An in MeOH and AN is greatly depended on the stability of the zwitterionic intermediate. The effect of ring activation is due to the ground state stabilization and the more efficient delocalization of the negative charge with a nitro group than with a ring-nitrogen in the transition state. The low activation enthalpies ΔH# and the highly negative activation entropies ΔS# are due to the intramolecular hydrogen bonding with the ammonio hydrogen present in the transition state.

An improved synthesis of(lS,4S)-2-oxa-5-azabicyclo[2.2.1]heptane

An improved and efficient method for synthesis of （1S,4S）-2-oxa-5-azabicyclo[2.2.1]heptane （1） from trans-4-hydroxy-L-proline was developed. Using benzyloxycarbonyl （Cbz） as protection group of amine, the reactions were in mild conditions, and the title compound I was accomplished in six steps in overall yield of 70%.