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CAS No. : | 182496-55-5 | MDL No. : | MFCD04038412 |
Formula : | C40H48O4S4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PDEJSTNRUYUEQL-UHFFFAOYSA-N |
M.W : | 721.07 | Pubchem ID : | 5242247 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
81% | With triphenylphosphine; diethylazodicarboxylate In toluene at 40℃; for 24h; | |
81% | With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 24h; Cooling; | Synthesis of compounds 1-3 (general procedure). General procedure: p-tert-Butylthiacalix[4]arene (2 g, 2.8 mmol), triphenylphosphine (2.18 g,8.3 mmol), appropriate alcohol (8.3 mmol), and anhydrous toluene (30 mL) were placed in a roundbottom flask. Diethyl azodicarboxylate (1.31 mL, 1.11 g mL-1, 8.3 mmol) was slowly added to the reaction mixture with cooling. The mixture was stirred for 24 h (48 h in the case of compound 3) at 20 C. Then the reaction mixture was concentrated to dryness on a rotary evaporator and precipitated with methanol. The precipitate was filtered and thrice washed with methanol. |
67% | With thiamine diphosphate; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With thiamine diphosphate; diethylazodicarboxylate In toluene at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.8% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere; | 1.1; 2.1 A method for preparing a fluorescent probe includes the following steps: In the first step, under a nitrogen atmosphere, 3.00 mmol of thiacup [4] arene, 25.71 mmol of hydroxyethylphthalimide,9.15 mmol of triphenylphosphine, 120 mL of dry tetrahydrofuran (drying treatment before use), stir well and cool to zero in an ice-salt bath.9.14 mmol of diethyl azodicarboxylate was dissolved in 30 mL of dry tetrahydrofuran, and then placed in a constant pressure funnel and slowly dropped into a three-necked flask. After the dropwise addition was completed, the temperature was raised to room temperature for 72 hours.At the end of the reaction, the solvent was evaporated to dryness, and methanol was added while hot to precipitate a large amount of white solid. After suction filtration, the filter cake was dried.Purification by silica gel column chromatography (n-hexane: ethyl acetate = 8: 2) to obtain 2.43 g of 1,3-alternate-bis (2-phthalimide) thiacalix [4] arene, yield Is 75.8%,1,3-Alternate-bis (2-phthalimide) thiacalix [4] arene has the structural formula shown in Formula (II): |
70% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 48h; | |
70% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; | 1 Synthesis of intermediate 2,4-bis (phthalimidoethyl) thiacalix [4] arene Team, in a 50 mL round bottom flask,The thiacalix [4] arene (721 mg, 1. OO mmol) was added,N-Light ethyl phthalimide(1.75 g, 8.57 mmol),Triphenylphosphine (800 mg, 3.05 mmol),Dry tetrahydrofuran 20 mL,Ice bath,Then diethylazodicarboxylate (531 mg, 3.05 mmol) was slowly added dropwise,After the addition, the reaction was stirred at room temperature for 48h,Hot methanol 20mL by adding, cooling,Precipitation of a large number of white solid crude products,The crude product was purified by column chromatography (eluent: ethyl acetate / n-hexane, ν / ν = 1/4) to give a white product, 748 mg, in 70% yield. |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tert-butylthiacalix[4]arene With potassium hydroxide In dichloromethane; water Stage #2: copper(II) 5,10,15,20-tetrakis(1-methyl-4-pyridyl)-21H,23H-porphine In dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -10 - 50℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; N,N-dimethyl acetamide at 130℃; for 72h; | DCPB (0.03 g, 0.08 mmol), DMA (5 ml), CH3OH (5 ml) and concentratedHCl (0.2 ml) were placed in a 20 ml Teflon-lined autoclavewhich was kept at 130 C for 3 days and then slowly cooled toroom temperature at about 4 C/h. Several purple block crystals of CIAC-205 were obtained. Elemental analysis (%): C 57.38, H 4.74;found: C 59.28, H 4.23. The EDS analysis reveals that the molar ratioof Co, S and Cl molar is 5.61: 5.48: 1.47, comparable to the expectedvalue 4: 4: 1. FT-IR (cm1): 3288(w), 3051(w), 2963(s),2855(w), 1934(w), 1589(s), 1548(s), 1439(s), 1399(s), 1304(w),1250(s), 1168(s), 1087(s), 1006(s), 844(s), 763(s), 701(s), 648(m),485(s), 451(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triphenylphosphine; diethylazodicarboxylate In toluene at 40℃; for 24h; | |
80% | With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 48h; Cooling; | Synthesis of compounds 1-3 (general procedure). General procedure: p-tert-Butylthiacalix[4]arene (2 g, 2.8 mmol), triphenylphosphine (2.18 g,8.3 mmol), appropriate alcohol (8.3 mmol), and anhydrous toluene (30 mL) were placed in a roundbottom flask. Diethyl azodicarboxylate (1.31 mL, 1.11 g mL-1, 8.3 mmol) was slowly added to the reaction mixture with cooling. The mixture was stirred for 24 h (48 h in the case of compound 3) at 20 C. Then the reaction mixture was concentrated to dryness on a rotary evaporator and precipitated with methanol. The precipitate was filtered and thrice washed with methanol. |
With triphenylphosphine; diethylazodicarboxylate In toluene at 40℃; for 24h; Inert atmosphere; | Compounds 2 and 3 General procedure: An appropriate alcohol (6.9 mmol), p-tert-butylthiacalix[4]arene 16 (2 g, 2.8 mmol), triphenylphosphine (2.22 g, 8.3 mmol)and diethyl azodicarboxylate (1.32 ml, 8.3 mmol) were dissolved in 20 mlof dry toluene under inert atmosphere. The reaction mixture was stirredat 40 °C for 24 h, and then the solvent was evaporated in vacuo. The crudematerial was washed twice with ethanol to give products 2 or 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 130℃; for 72h; High pressure; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In methanol at 130℃; for 72h; High pressure; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In methanol; water at 130℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With tetramethyl ammoniumhydroxide In water at 130℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.61% | In methanol; N,N-dimethyl-formamide at 130℃; for 72h; Autoclave; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol; N,N-dimethyl-formamide at 130℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium carbonate In acetone for 8h; Reflux; | Synthesis of TCAN2PA To a solution of thiacalix[4]arene (0.5 g, 0.00069 mol),K2CO3(0.19 g, 0.0014) in dry acetone, N-(4-(tert-butyl)phenyl)-2-chloroacetamide (0.31 g, 0.0014 mol) was added.The reaction mixture was then refluxed for 8 h. The progressof the reaction was monitored through TLC. After completion,the reaction mixture was cooled to room temperature,and the solvent was evaporated to dryness. The pure compound(Scheme 1) was obtained by silica gel column chromatographyby using (hexane: ethyl acetate) as eluents (9:1)to get the solid product with 70% yield.MS (ESI): m/z for C63H75N2O6S4Calcd: 1084.5 [M],Found 1123.4 [M + Na]+(Fig. S8), [1] H-NMR (400 MHz,DMSO-d6): δ (ppm): 0.94 (18H, s,-CH3), 1.38(36H, s,-CH3), 5.1(4H, s, -CH2), 8.8(2H, s, -OH) (Fig. S9) 10.1 (2H,s, -NH), 7.5(8H, s, Ar-H), 7.3(4H, s, Ar-H), 2.5(DMSO);[13] C NMR (100 MHz, DMSO): δ (ppm): 30.61, 34.69,76.71, 77.03, 77.35, 120.54, 136.42, 144.71, 155.63(Fig. S10); M.P: 275.0 °C. |