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CAS No. : | 13104-56-8 | MDL No. : | MFCD06796987 |
Formula : | C22H17N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QAEWAYWLMREGRA-UHFFFAOYSA-N |
M.W : | 339.39 | Pubchem ID : | 630929 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.05 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 102.63 |
TPSA : | 47.9 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.84 cm/s |
Log Po/w (iLOGP) : | 3.59 |
Log Po/w (XLOGP3) : | 3.56 |
Log Po/w (WLOGP) : | 4.88 |
Log Po/w (MLOGP) : | 2.0 |
Log Po/w (SILICOS-IT) : | 4.99 |
Consensus Log Po/w : | 3.8 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.61 |
Solubility : | 0.00841 mg/ml ; 0.0000248 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.25 |
Solubility : | 0.019 mg/ml ; 0.0000561 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.93 |
Solubility : | 0.000000402 mg/ml ; 0.0000000012 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.62% | Stage #1: With potassium hydroxide In ethanol at 20℃; for 0.166667 h; Stage #2: With ammonium hydroxide In ethanol at 37℃; for 24 h; |
General procedure: Synthesis of 4′-(3-methoxyphenyl)-2,2′:6′,2″-terpyridine (3-MeO-Phtpy), 4′-(2-methoxyphenyl)-2,2′:6′,2″-terpyridine (2-MeO-Phtpy) and 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine (4-MeO-Phtpy) were performed using the methods described previously [27–33]. 2-Acetylpyridine (2.813g, 23.2mmol, 2 eq.) was added to 2-methoxybenzaldehyde, 3-methoxybenzaldehyde or 4-methoxybenzaldehyde (11.6mmol, 1 eq.) dissolved in 50mL ethanol. KOH pellets (46.5mmol, 4 eq.) were added to this solution. The reaction mixture was stirred at room temperature for 10min. NH3 (40mL, 25percent aq.) was slowly added to the reaction mixture. After a 24-h incubation at 37°C, 5mL of 25percent aq. NH3 was added to the reaction mixture again. The flask containing the reaction mixture was cooled to−20°C. The obtained white precipitate in the flask was isolated through filtration and washed with cold ethanol. We further purified the each product using recrystallization in ethanol-H2O. After recrystallization, each product was recovered by filtration, washed with cold ethanol and petroleum ether, and dried under high vacuum for 24h (Scheme 1). |
37% | With ammonium hydroxide; potassium hydroxide In ethanol at 20℃; for 24 h; | General procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde,4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1,L4, L7) or toluene (L2, L3, L5, L6, L8,L9) afforded a crystalline solid. 4′-(4-methoxy-1-phenyl)-2,2′:6′,2″-terpyridine (L1): Yield: 37percent. IR(KBr, cm−1): 1588(s), 1467(m), 1389(m), 1204(m), 1157(m),1069(m), 790(m), 739(m) and 655(m). NMR: 1H NMR (400 MHz,CDCl3) δ 8.73 (d, J=4.1 Hz, 2H, HA1), 8.71 (s, 2H, HB2), 8.67 (d,J=7.9 Hz, 2H, HA4), 7.90–7.85 (m, 4H, HC2+A3), 7.37–7.33 (m, 2H,HA2), 7.03 (d, J=8.7 Hz, 2H, HC3), 3.88 (s, 3H, HC5). 13C NMR(100 MHz, CDCl3) δ 160.66, 156.55, 155.99, 149.90, 149.24, 136.96,130.92, 128.67, 123.87, 121.49, 118.42, 114.46, 55.52. C22H17N3O(339.39 g mol−1): calcd C, 77.86; H, 5.05; N, 12.38percent; found: C, 77.46;H, 5.35; N, 12.25percent. DSC: (I run) Tm=164 °C; (II run) Tg=30, Tc=82and Tm=163 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.62% | General procedure: Synthesis of 4?-(3-methoxyphenyl)-2,2?:6?,2?-terpyridine (3-MeO-Phtpy), 4?-(2-methoxyphenyl)-2,2?:6?,2?-terpyridine (2-MeO-Phtpy) and 4?-(4-methoxyphenyl)-2,2?:6?,2?-terpyridine (4-MeO-Phtpy) were performed using the methods described previously [27-33]. 2-Acetylpyridine (2.813g, 23.2mmol, 2 eq.) was added to 2-methoxybenzaldehyde, 3-methoxybenzaldehyde or 4-methoxybenzaldehyde (11.6mmol, 1 eq.) dissolved in 50mL ethanol. KOH pellets (46.5mmol, 4 eq.) were added to this solution. The reaction mixture was stirred at room temperature for 10min. NH3 (40mL, 25% aq.) was slowly added to the reaction mixture. After a 24-h incubation at 37C, 5mL of 25% aq. NH3 was added to the reaction mixture again. The flask containing the reaction mixture was cooled to-20C. The obtained white precipitate in the flask was isolated through filtration and washed with cold ethanol. We further purified the each product using recrystallization in ethanol-H2O. After recrystallization, each product was recovered by filtration, washed with cold ethanol and petroleum ether, and dried under high vacuum for 24h (Scheme 1). | |
37% | With ammonium hydroxide; potassium hydroxide; In ethanol; at 20℃; for 24h; | General procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde,4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1,L4, L7) or toluene (L2, L3, L5, L6, L8,L9) afforded a crystalline solid. 4?-(4-methoxy-1-phenyl)-2,2?:6?,2?-terpyridine (L1): Yield: 37%. IR(KBr, cm-1): 1588(s), 1467(m), 1389(m), 1204(m), 1157(m),1069(m), 790(m), 739(m) and 655(m). NMR: 1H NMR (400 MHz,CDCl3) delta 8.73 (d, J=4.1 Hz, 2H, HA1), 8.71 (s, 2H, HB2), 8.67 (d,J=7.9 Hz, 2H, HA4), 7.90-7.85 (m, 4H, HC2+A3), 7.37-7.33 (m, 2H,HA2), 7.03 (d, J=8.7 Hz, 2H, HC3), 3.88 (s, 3H, HC5). 13C NMR(100 MHz, CDCl3) delta 160.66, 156.55, 155.99, 149.90, 149.24, 136.96,130.92, 128.67, 123.87, 121.49, 118.42, 114.46, 55.52. C22H17N3O(339.39 g mol-1): calcd C, 77.86; H, 5.05; N, 12.38%; found: C, 77.46;H, 5.35; N, 12.25%. DSC: (I run) Tm=164 C; (II run) Tg=30, Tc=82and Tm=163 C. |
With ammonium hydroxide; potassium hydroxide; In ethanol; at 20℃; for 8h; | General procedure: All tridentate ligands were synthesized by following literature procedure [18]. 2-Acetyl pyridine (20.0 mmol) was added to an ethanolic solution of various aldehydes (10.0 mmol in 70 mL EtOH). KOH pellets (26 mmol) and 30 mL aqueous NH3 (25%)were added to the solution and was stirred at room temperature for 8 h. An off-white solid formed which was collected by filtration, followed by washings with H2O (3 × 10 mL) and EtOH (2 × 5 mL). Crystallization from CHCl3-MeOH system gives a white crystalline solid. Scheme which contains proposed reaction of ligand has been kept in Supplementary Material. |
With ammonia; potassium hydroxide; In ethanol; water; at 20℃; for 8h;Inert atmosphere; | General procedure: All tridentate ligands were synthesized similarly by followingliterature procedure [31]. 2-Acetyl pyridine (20.0 mmol) wasadded to an ethanolic solution of various aldehydes (10.0 mmolin 70 mL EtOH). KOH pellets (26 mmol) and aqueous NH3 (25%,0.425 mol) were added to the solution and was stirred at roomtemperature for 8 h. An off-white solid formed which was collectedby filtration, followed by washings with H2O (3 10 mL) and EtOH(2 5 mL). Crystallization from CHCl3-MeOH system gives a whitecrystalline solid. The proposed reaction is shown in Scheme 1. | |
With ammonia; potassium hydroxide; In ethanol; water; at 20℃; | General procedure: 2-acetylpyridine(0.200 g, 0.165 mmol) dissolved in ethanol (10 mL) was added intoan ethanol solution of 0.8 mmol 3-methoxybenaldehyde (0.0110 g,0.082 mmol). KOH pellets (0.15 g, 2.7 mmol) and NH3 (aq., 1.49 mL,25%, 20 mmol) were then added to the mixture. After stirring at roomtemperature overnight, the solid was collected by filtration andwashedwith ethanol. | |
With ammonia; potassium hydroxide; In ethanol; water; at 20℃; for 16h;Inert atmosphere; | The terpyridyl ligand was synthesized by the reported procedure [36]. 4-Methoxybenzaldehyde (0.680 g, 5 mmol) and 2-acetylpyridine (1.21 g, 10 mmol) were dissolved in ethanol. KOH (0.77 g, 10 mmol) was added and the mixture was vigorously stirred. After the potassium hydroxide pellets completely dissolved, ammonia (excess, ca. 20 mL) was added and the mixture was stirred at room temperature for 16 h under N2. The resulting solution was filtered under vacuum and washed with ethanol to give a very light blue fluffy solid (yield: 0.678 g, 40%). The crude product was recrystallized from methanol. Mass spectrum (ESI + ve) (m/z): observed 340.2 (M + 1); Calcd 339 (M). 1H NMR (CDCl3, delta): 8.72 (4H, d, HA, K), 8.66 (2H, s, HG), 7.85-7.89 (4H, m, HD,J), 7.36 (2H, m, HC), 7.07 (2H, dd, HB), 3.846 (3H, s, HN). 13C NMR (CDCl3, delta): 160.54CF, 155.63 CE, 155.27 CA, 149.03 CH, 148.61 CK, 137.33 CC, 130.41 CL, 128.54 CI, 123.85 CB, 121.58 CD, 118.48 CG, 114.30 CJ, 56.56 CN. | |
With ammonia; potassium hydroxide; In ethanol; at 20℃; | General procedure: The one-pot preparation method of Krohnke type 4'-aryl-2,2':6',2''-terpyridine ligands was performed to obtainligands L1-L5 according to the literature [23] with aslight modification. 2-Acetylpyridine (0.56 cm3,5.0 mmol) was added to a solution of 0.25 cm3 benzaldehyde(2.5 mmol) in 18 cm3 ethanol. After addition of the mixture of 0.280 g KOH (5.0 mmol) and 0.5 cm3 NH3(25 %, 6.5 mmol), the solution was stirred overnight at room temperature, during which time as orange suspension was appeared. The solid was collected by filtration and washed with EtOH (3 9 6 cm3). Then, the crude solid product was recrystallized by cooling the hot super saturated ethanolic solution. The preparation method of diketone ligand (L6) was performed similar to the above procedure for the preparation of substituted phenyl terpyridines without the addition of ammonia. The prepared ligand was characterized in good agreement with the literature [24]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In methanol; chloroform; at 20℃; | General procedure: The complexes were synthesized according to the same method: a methanol solution (10 mL) of ZnX2 (1 mmol) was added with stirring to a chloroform solution (10 mL) of the corresponding terpyridine derivative (0.1 mmol). The mixture was stirred at room temperature for 10 min to give a white to yellow precipitate. Colorless to yellow block-shaped crystals of the complexes were formed by slow diffusion of methanol into the concentrated DMSO solution of the complexes. Yield: 87% (1), 89% (2), 92% (3), 85% (4), 89% (5) and 91% (6) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | 2.3 Synthesis of [Cu(meotpy)(dmp)](NO3)2·H2O (1) The ligands, meotpy and bitpy were synthesized employing the procedure reported in literature [40] . Briefly, the complex 1 was prepared by stirring a methanolic solution of Cu(NO3)2·3H2O (0.12 g, 0.5 mmol) with meotpy (0.15 g, 0.5 mmol) at room temperature for 30 min. Subsequently, dmp (0.12 g, 0.5 mmol) was added to the above solution and stirred continuously for another 30 min. A green solid that separated out upon slow evaporation of the solvent was filtered, and washed with diethyl ether and dried in vacuum. The complex was recrystallized from an acetonitrile solution. Yield: 79%. Found: C, 68.61; H, 5.18; N, 11.18. Anal Calcd for C36H33CuN5O2: C, 68.50; H, 5.27; N, 11.09. ESI-MS m/z: 305. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.4% | With sodium methylate; In methanol; for 2h;pH Ca. 6.8;Reflux; | General procedure: Methanolic solution of CuCl2·2H2O (1.5 mmol) was added to a methanolic solution of 4?-(3-chlorophenyl)-2,2?:6?,2?-terpyridine (L1) (1.5 mmol), followed by the addition of a previously prepared methanolic solution of sparfloxacin (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ~6.8. The resulting solution was refluxed for 2 h. on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane and dried in a vacuum desiccator. The proposed reaction scheme for the synthesis of complex has been kept in the Supplementary Material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In methanol; ethanol; for 2h;pH Ca. 6.8;Reflux; Inert atmosphere; | Ethanolic solution of CuCl2*2H2O (1.5 mmol) was added to a ethanolic solution of 40-substituted-2,20:60,20 0-terpyridine (L1-3)(1.5 mmol), followed by the addition of a previously prepared methanolic solution of clioquinol (1.5 mmol) in presence of CH3-ONa (1.5 mmol). The pH of the reaction mixture was adjusted to 6.8. The resulting solution was refluxed for 2 h on a water bath, followed by concentrating to half of its volume. A fine, dark brown amorphous product obtained was washed with ether/hexane and dried in vacuum desiccators in Scheme 2. Physical properties and analytical data of copper(II) complexes with clioquinol and terpyridines in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20℃; | General procedure: A solution of CuCl2·2H2O (0.05 g, 0.3 mmol) dissolved in methanol(5 mL) was added to a methanol solution (10 mL) containing the L1(0.1017 g, 0.3 mmol). The mixture was stirred at room temperatureovernight. The green precipitate was collected and dried with ethylether, recrystallized inmethanol. The obtained productswere identifiedby IR spectra, ES-MS spectra and EPR spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In ethanol; chloroform; at 20℃;Reflux; | General procedure: MnCl2.4H2O (1 mmol) was dissolved in alcohol (10 mL), Ligand(1 mmol) was dissolved in CHCl3 and was added dropwise to the above solution with stirring at room temperature in 1 h. Then the solution was refluxed for 4 h. The mixture was allowed to stay overnight at -10C, after which the precipitate was filtered off, washed with diethyl ether, and dried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | 4,4?-bipyridine (23mg, 0.15 mmol) and atpy (51 mg, 0.15 mmol) in CH2Cl2 was added to a solution of Cu(CH3COO)2·H2O (30 mg, 0.15 mmol) in methanol (15 mL). After stirring for 10min, an excess of NH4PF6 (60 mg, 0.37 mmol) was added to solution. The reaction mixture was then stirred for 2 h. The solvent was removed at reduced pressure and the green residue was precipitated using diethyl ether. Yield: 32mg, 31%; m.p. 233-235 C (dec.). Anal. Calc. for C58H48Cu2F12N8O6P2·1.5H2O. CH2Cl2: C, 47.72; H, 3.54; N, 7.42. Found: C, 47.26; H, 3.03; N, 7.99%. TGA-DTA: calc. by formula C58H48Cu2F12N8O6P2·0.5H2O: H2O%=0.64, 2(CH3COO)%=8.44, 4,4?-bpy%=12.18, Cu(CH3COO)2%=16.18. Determined H2O%=0.71, 2(CH3COO)%=6.15, 4,4?-bpy%=12.81, Cu(CH3COO)2%=16.91. IR data (KBr, cm-1): 3389, 3055, 1598, 1470, 1407, 1243, 1189, 1019, 835, 794, 688, 641, 586, 519. Green crystals of 3 were obtained from a MeOH/diethyl ether solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | The ligand OMePh-tpy (0.220 g, 0.648 mmol)and [RuCl2(PPh3)3] (0.621 g, 0.648 mmol) in methanol (40 mL) were placed in a roundbottom flask (50 mL) and the mixture refluxed for 5 h. Upon cooling the solution to roomtemperature, NH4PF6 (0.150 g, 0.920 mmol) was added and the system is stirred for 2 h.The precipitate was filtered and purified by chromatography over aluminum oxide using atoluene/acetone mixture (1 : 1) as eluent. The eluate was evaporated to dryness by rotaryevaporation, the residue dissolved in a minimal amount of acetone and diethyl ether addedto precipitate the solid, which was filtered and dried in a vacuum oven at 60 C. Yield: 95% (0.702 g), m.p. 300 C (d). IR (KBr, nu cm-1): 3057(C-H), 1604(C=C), 1518(C=N),1179(P-Ph), 1091(P-Ph), 845(PF6 ), 557(PF6 ). 1H NMR (delta ppm; J, Hz): 9.29 (d, Hd, 3J Hdc= 7.16), 8.21(d, Ha, 3J Ha-b = 6.09), 8.01(s, He), 7.87 (AB, Hf, and d, Hc, 3J Hf-c = 8.95),7.40 (dd, Hb, 3J Hb-a = 6.09), 7.34-7.17(AB, Hg and PPh3), 3.96 (s, OCH3). 31P NMR (deltappm): 17.1 (s, PPh3), -146 (qt, PF6 ). Anal. Calcd (%) for C58H47ClF6N3OP3Ru: C, 60.00;H, 4.14; N, 3.67. Found (%): C, 60.00; H, 4.20; N, 3.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 75℃; for 3h; | Accurately weighed Eu(TTA)2.4H2O 1.375 g, terpyridine (Tpy-OCH3) 0.658 g. Then added to a round-bottomed flask, completely dissolved in 50 ml of THF (tetrahydrofuran) and then warmed to 75 C. The reaction was heated for 3 hours under a magnetic stirrer. After the completion of the reaction, the solvent was removed, (TTA)2Tpy-OCH3 was prepared by vacuum drying at 60 C for 24 hours, and the calculated yield was weighed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In methanol; for 3h;Reflux; Inert atmosphere; | L1 (1.5 mmol) and RuCl3 (0.40 g, 1.5 mmol) were dissolved in 20 mL of dry methanol and heated to reflux under N2 for 3 h. The resulting deep brown solution was allowed to cool at room temperature, after which the solution was cooled in an ice-bath for 0.5 h. The brown solid was collected by vacuum filtration and washed with cold methanol until the filtrate was colorless and then washed with Et2O and air-dried. The product (yield: 0.662 g, 72%) was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In dichloromethane; at 20℃; | General procedure: To a solution of 55 mg dimethyltin dichloride (0.25 mmol)in 5 cm3 dichloromethane was added a solution of 77 mg Phtpy (L1, 0.25 mmol) in 5 cm3 dichloromethane. The mixture was then stirred overnight at room temperature. In the case of soluble product, the solvent was evaporated to concentrate. Then, the solid was formed by the addition of diethyl ether. It was washed two times more with diethylether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In ethanol; at 160℃; for 75h;Autoclave; | General procedure: A mixtureof CuSO4 · 5H2O (0.05 mmol, 0.0125 g), Meophtpy (0.1 mmol, 0.0340 g) and NaClO4 (0.1 mmol, 0.0122 g) in 95% EtOH (10 mL) were sealed in a 15 mL Telfon-lined stainless steel container, which was heated to 160C for 48 h. After cooling to room temperature at a rate of 5 K h-1, the green block crystals were obtained in about 55% yield based on Cu. IR (KBr; nu, cm-1): 3566.38 m, 3068.75 m,3014.74 m, 2935.66 m, 2839.22 m, 2015.61w,1869.02 w, 1600.92 v.s, 1575.84 s, 1544.98 s, 1519.91 s,1473.62 v.s, 1433.11 s, 1408.04 s, 1365.60 m,1307.74 m, 1280.73 m, 1246.02 v.s, 1184.29 v.s,1163.08 m, 1089.78 v.s, 1016.49 v.s, 831.47 m,831.32 v.s, 792.74 v.s, 746.45 m, 731.02 m, 688.59 m,657.73 m, 621.08 v.s, 582.50 s, 520.76 m, 472.56 m,455.20 m, 433.98 m, 414.70 m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In ethanol; at 160℃; for 75h;Autoclave; | General procedure: A mixtureof CuSO4 · 5H2O (0.05 mmol, 0.0125 g), Meophtpy (0.1 mmol, 0.0340 g) and NaClO4 (0.1 mmol, 0.0122 g) in 95% EtOH (10 mL) were sealed in a 15 mL Telfon-lined stainless steel container, which was heated to 160C for 48 h. After cooling to room temperature at a rate of 5 K h-1, the green block crystals were obtained in about 55% yield based on Cu. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.9% | In methanol; dimethyl sulfoxide; at 80℃; for 48h;Inert atmosphere; Sealed tube; | General procedure: IrCl3 (0.0299g, 0.1mmol) was mixed with 3-MeO-Phtpy, 2-MeO-Phtpy or 4-MeO-Phtpy (0.0339g, 0.1mmol), 0.20mL DMSO and 0.50mL CH3OH in a Pyrex tube. The Pyrex tube containing the reaction mixture was then placed in liquid N2, vacuumed and sealed. The reaction was initiated by heating the reaction mixture to 80C. After two days of incubation at 80C, the resulting brown-black crystals were isolated and characterized by different spectroscopic and analytic techniques. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.7% | In acetonitrile; for 0.166667h;Sonication; | A mixture of Ni(NO3)2.6H2O (0.070g, 0.24 mmol), meophtpy(0.078 g, 0.023 mmol) and NaClO4 (0.028 g, 0.023 mmol) inacetonitrile (30 mL) was sonicated for 10min. The resulted clearsolution was left alone until many brown crystals were obtained.Yield: 0.005g, 44.7%. Calcd. For C44H38Cl2N6NiO12 (1): C, 56.61;H, 4.17; N, 10.60%. Found: C, 56.76; H, 4.11; N, 10.67%. IR(KBr,cm1): 3066.82(w), 1600.92(vs), 1519.91(s), 1473.61(s), 1435.04(s), 1367.53(s), 1240.23(s), 1192.01(m), 1087.85(vs), 1024.20(s), 829.39(s), 794.67(vs), 729.09(m), 657.72(m), 621.08(m), 584.43(m), 518.85(m), 418.55(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol; for 3h;Reflux; Darkness; | 4'-(4-methoxyphenyl)-2,2':6',2"-terpyridine (250?mg, 0.74?mmol) was dissolved in EtOH (96%, 48?mL) upon slight heating. RuCl3·xH2O (40-49% Ru, 192?mg, 0.76?mmol) was then added. The mixture was refluxed for 3?h, protected from light. The mixture was cooled down to room temperature and the volume of the solution was reduced to 15-20?mL by evaporation of ethanol under reduced pressure. The mixture was left in a freezer for 2?h and then the solid was filtrated. The precipitate was rinsed thoroughly with cold water until the water becomes colorless, and finally washed with cold ethanol (4-5?mL) and ether. The resulting solid was dried in vacuum and obtained as a black powder. Yield: 335?mg (83%). Elemental analysis found: C, 48.83; H, 3.05; N 7.60%. C22H17Cl3N3ORu requires C, 48.32; H, 3.13; N, 7.68%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium perchlorate; In water; for 336h; | [Mn(nme2phtpy)2](ClO4)2*2CH3CN (4) was prepared in the following way: two drops of a 50% aqueous solution of Mn(NO3)2 (ca. 0.24 mmol), nme2phtpy (0.23 mmol, 0.081 g), and NaClO4 (0.48 mmol, 0.067 g) were dissolved in 30 ml of CH3CN. Then a few drops of water were added until the solution became clear. A crop of brown crystals was obtained in two weeks. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; for 336h; | Co(NO3)2*6H2O (67 mg, 0.24 mmol), meophtpy (78 mg, 0.23 mmol), and NaClO4 (67.2 mg, 48 mmol) were dissolved in 30 ml of CH3CN. A few drops of water were added until the solution became clear. A crop of purple crystals was obtained in two weeks. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In water; acetonitrile; at 150℃; for 20h;High pressure; Autoclave; | Re(CO)5Cl (0.10 g, 0.27 mmol) and suitable Ln ligand (0.27 mmol) were dissolved in argon-saturated acetonitrile (20 mL). The resulting solution was placed in 25 mL teflon lined hydrothermal synthesis autoclave reactor and heated to 150 C. The reaction was stopped after 20 h and the autoclave was gradually cooled to room temperature for 30 h. The resulting yellow (1, 4, 7) or orange (2, 3, 5, 6, 8, 9) solid was collected by filtration, washed with diethyl ether and dried. X-ray quality orange (2 and 8) crystals were obtained by recrystallization from mixture of acetonitrile/methanol. To synthetize the complexes 1-9, standard procedure based on the heating under reflux of [Re(CO)5Cl] with molar equivalent of Ln ligand in argon-saturated acetonitrile also may be used. [ReCl(CO)3(L1)] (1): Yield: 75%. IR (KBr, cm-1): 2022(vs),1936(vs) and 1910(vs) nu(C^O); 1604(m) nu(C]N) and nu(C]C). 1HNMR (400 MHz, DMSO-d6) delta/ppm=9.11 (d, J=8.2 Hz, 1H, HC4),9.07-9.04 (m, 2H, HC1+B2), 8.79 (d, J=4.5 Hz, 1H, HA1), 8.39 (t,J=7.7 Hz, 1H, HC3), 8.22 (d, J=8.7 Hz, 2H, HD2), 8.15 (s, 1H, HB4),8.05 (t, J=8.0 Hz, 1H, HA3), 7.89 (d, J=7.6 Hz, 1H, HA4), 7.77 (t,J=6.2 Hz, 1H, HC2), 7.65-7.60 (m, 1H, HA2), 7.16 (d, J=8.6 Hz, 2H,HD3), 3.88 (s, 3H, HD5). 13C NMR (100 MHz, DMSO-d6): delta/ppm=198.25, 194.94, 191.50 (3CO), 162.18, 161.77, 158.39, 157.44,156.83, 153.13, 150.66, 149.67, 140.39, 137.37, 129.95, 127.85,127.18, 125.83, 125.59, 125.36, 123.86, 120.18, 115.29, 55.99. DSC: (Irun) Tm=308 C; (II run) Tg=246 C. C25H17N3O4ClRe(645.08 g mol-1): calcd C, 46.55; H, 2.66; N, 6.51; found: C, 46.18; H,2.80; N, 6.24. |
Tags: 13104-56-8 synthesis path| 13104-56-8 SDS| 13104-56-8 COA| 13104-56-8 purity| 13104-56-8 application| 13104-56-8 NMR| 13104-56-8 COA| 13104-56-8 structure
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