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CAS No. : | 14316-14-4 | MDL No. : | MFCD00464177 |
Formula : | C9H13NO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SIIWTWXTZDDNTI-UHFFFAOYSA-N |
M.W : | 215.27 | Pubchem ID : | 1895595 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 53.27 |
TPSA : | 74.78 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.21 cm/s |
Log Po/w (iLOGP) : | 1.41 |
Log Po/w (XLOGP3) : | 0.57 |
Log Po/w (WLOGP) : | 1.35 |
Log Po/w (MLOGP) : | 0.43 |
Log Po/w (SILICOS-IT) : | 0.55 |
Consensus Log Po/w : | 0.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.59 |
Solubility : | 5.57 mg/ml ; 0.0259 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.71 |
Solubility : | 4.17 mg/ml ; 0.0194 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.0 |
Solubility : | 0.214 mg/ml ; 0.000993 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.16 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
100% | With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; | |
99% | With triethylamine In dichloromethane at 0 - 20℃; for 24h; | |
96% | With pyridine at 5 - 20℃; |
94% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; | |
91% | With zinc oxide-nanoparticle at 50℃; Neat (no solvent); chemoselective reaction; | |
90% | With tetrabutylammomium bromide; sodium hydroxide In benzene at 0 - 20℃; for 8h; | |
90% | With tetrabutylammomium bromide; sodium hydroxide In benzene at 0 - 20℃; for 8h; | |
89% | With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3h; stereoselective reaction; | |
89% | With triethylamine In dichloromethane at 0 - 20℃; | |
85% | With triethylamine In dichloromethane at 20℃; | |
83% | With triethylamine In dichloromethane at 0 - 20℃; for 18h; | |
81% | With triethylamine In dichloromethane at 0 - 25℃; for 0.333333h; | |
70% | In toluene Heating; | |
70% | With triethylamine In dichloromethane at 0 - 20℃; | |
70% | With triethylamine In dichloromethane at 20℃; for 18h; Schlenk technique; Cooling with ice; | |
68% | With triethylamine In dichloromethane at 0℃; for 8h; | |
68% | With triethylamine In dichloromethane at 20℃; for 17h; Sealed tube; Inert atmosphere; | |
61% | With triethylamine In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; Cooling with ice; | |
43% | With dmap; triethylamine In dichloromethane at 0 - 20℃; | General procedure for the preparation of N-protected aminoalcohols General procedure: To a solution of aminoalcohol (10 mmol), DMAP (1 mmol) and triethylamine (20 mmol) in CH2Cl2(2.0 M) at 0 °C, a solution of the suitable sulfonyl chloride was added dropwise (10.5 mmol) inCH2Cl2 (50 mL) and the resulting mixture was stirred at room temperature overnight. The mixturewas washed with water (3 x 50 mL) and brine (1 x 50 mL), then dried over Na2SO4, andconcentrated at reduced pressure. The crude product was purified by silica gel columnchromatography to afford the corresponding protected aminoalcohol. |
With pyridine | ||
With sodium hydroxide | ||
With sodium hydroxide In benzene | ||
In N,N-dimethyl-formamide | ||
With hydrogenchloride In dichloromethane; water | a I. a) 100 g of p-toluenesulfonyl chloride are slowly added over 1.5 hour to 80 ml of ethanolamine while cooling with ice. The reaction mixture is then heated to 120° C. and is then held at this temperature for 3 hours. After cooling to 70° C., a mixture of 60 ml of concentration HCl and 300 ml of water is added. After stirring for 10 min, 300 ml of methylene chloride are added, and the organic phase is separated and dried with MgSO4. After stripping off the solvent on the rotary evaporator, 111.6 g of a slightly yellowish solid [N-(2-hydroxyethyl)-p-toluenesulfonamide] are obtained. The product can be used in the next step without further purification. | |
With sodium hydroxide; tetrabutylammomium bromide In water; benzene | ||
With triethylamine In tetrahydrofuran; water at 0 - 20℃; | ||
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | ||
With triethylamine In dichloromethane at 20℃; for 16h; | ||
With triethylamine In dichloromethane at 20℃; | ||
With triethylamine In chloroform at 20℃; for 16h; | ||
With triethylamine In dichloromethane | ||
With triethylamine In dichloromethane at 20℃; | ||
With silica gel for 0.5h; Inert atmosphere; | ||
With triethylamine In dichloromethane at 20℃; | ||
With triethylamine In dichloromethane at 20℃; | ||
With silica gel Inert atmosphere; | ||
In ethyl acetate at 20℃; for 2h; | Typical procedure for the synthesis of starting materials General procedure: Tosylation: To a solution of p-toluenesulfonyl chloride (5 mmol, 1.0 equiv) in EtOAc (10 mL) was added proper alkanolamine (10 mmol, 2.0 equiv). The reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was filtered through silica and washed with EtOAc. The residue was concentrated to give products, which were used to next step without further purification. | |
2 g | With triethylamine In dichloromethane at 20℃; Inert atmosphere; | |
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique; | ||
With triethylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; | ||
With dmap; triethylamine In dichloromethane at 0 - 20℃; | ||
With triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 25℃; for 24h; | |
With phosphorus tribromide | ||
With phosphorus tribromide In 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium carbonate In N,N-dimethyl-formamide | |
65% | With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 24h; | |
(i) KOtBu, (ii) /BRN= 605317/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tetramethlyammonium chloride In ethanol at 25℃; μ=0.16 M; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 1H-imidazole In dichloromethane at 20℃; for 22h; Inert atmosphere; | |
90% | With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h; | |
84% | With 1H-imidazole In dichloromethane at 25℃; for 22h; |
72% | With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | General procedure for the preparation of O-(tert-butyldimethylsilyl)-N-protectedaminoalcohol General procedure: A solution of N-protected aminoalcohol (10 mmol), tert-butyldimethylsilyl chloride (20 mmol) andimidazole (20 mmol) in DMF (0.2 M) was stirred at room temperature overnight. The reaction wastaken with brine (40 mL), extracted with Et2O (3 x 40 mL), dried over Na2SO4 and concentrated atreduced pressure. The crude product was purified by silica gel column chromatography to affordthe corresponding O-(tert-butyldimethylsilyl)-N-protected aminoalcohol.3 |
With 1H-imidazole In N,N-dimethyl-formamide Yield given; | ||
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; | ||
With 1H-imidazole In dichloromethane at 0℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triphenylphosphine In acetonitrile at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triphenylphosphine In acetonitrile at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C | ||
Multi-step reaction with 3 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C 4: 57 percent / NaOH / H2O; diethyl ether / 12 h 5: 1.) sodium / 1.) EtOH, 60 deg C, 30 min; 2.) DMF, 100 deg C, 1 h | ||
Multi-step reaction with 5 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction 4: 57 percent / H2O; diethyl ether 5: 1.) NaH / 1) DMF; 2) DMF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C 4: 57 percent / NaOH / H2O; diethyl ether / 12 h | ||
Multi-step reaction with 4 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction 4: 57 percent / H2O; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 65 percent / K2CO3 / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C | ||
Multi-step reaction with 2 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium phosphate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 130℃; for 21h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium phosphate In N,N-dimethyl-formamide at 110℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium carbonate In acetonitrile for 0.166667h; Reflux; | |
With potassium carbonate In acetone | ||
5.5 g | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 16h; |
With potassium carbonate In acetone Reflux; | ||
With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere; | ||
With potassium carbonate In acetone for 2h; Reflux; | ||
With potassium carbonate; potassium iodide In acetone for 16h; Inert atmosphere; Reflux; | ||
Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With camphor-10-sulfonic acid In 1,2-dichloro-ethane at 20 - 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; | |
89% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; | |
56% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine |
With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In acetone for 12h; | |
90% | With potassium carbonate In acetone for 12h; | |
81% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; |
62% | With potassium carbonate; potassium iodide In acetone for 16h; Reflux; | |
55% | With potassium carbonate; potassium iodide In acetone at 60℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In acetone for 12h; | |
224 g | With potassium carbonate In acetone at 20℃; for 16h; | |
With potassium carbonate In acetone Reflux; |
With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere; | ||
With potassium carbonate In acetone Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 30℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 17h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 17h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 30℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 120h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dipotassium peroxodisulfate; palladium diacetate; toluene-4-sulfonic acid In toluene at 20℃; for 16h; Sealed tube; | 4.3. General procedure for the synthesis of benzoxazines General procedure: An oven-dried stoppered round-bottom flask was charged with Pd(OAc)2 (10 mol%), sulfonamide (0.19 mmol), p-TsOH (108 mg, 0.57 mmol) and potassium persulfate (513 mg, 1.9 mmol) in 3mL of dry toluene. The reaction mixture was stirred for 5 min temperature, and then alkene (0.49 mmol) was added and stirred for 16 h at room temperature. The resulting dark brown reaction mixture was titrated with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combine organic layer was dried over anhydrous sodium sulfate and solvent was removed under reduced pressure. The crude reaction mixture was purified by column chromatography over silica gel using mixture of ethyl acetate and petroleum ether (10: 90) as eluent. |
79% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium carbonate In acetone at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium carbonate In acetone at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cesium fluoride supported on Celite at 50℃; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In acetone Reflux; | |
73% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; | |
56% | With potassium carbonate; potassium iodide In acetone for 16h; Reflux; |
With potassium carbonate; potassium iodide In acetone at 20℃; Reflux; | ||
With potassium carbonate In acetone Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With Tri(p-tolyl)phosphine In dichloromethane for 48h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With Tri(p-tolyl)phosphine In dichloromethane for 48h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With Nonafluorobutanesulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 1h; | The general procedure for the RfSO2F-induced cyclodehydration of b-hydroxysulfonamide to the corresponding aziridine General procedure: At room temperature, n-C4F9SO2F(4.0 mmol, 2.0 M equiv) was slowly added via syringe to a solution of bhydroxysulfonamide (2.0 mmol) and Et3N (6.0 mmol, 3.0 M equiv) in CH2Cl2,and the resulting mixture was stirred at room temperature for 1-2 h. Afterevaporation of the reaction mixture to remove volatile components, theresidue obtained was purified through silica gel column chromatography(petroleum:ethyl acetate = 10:1, v/v), providing the corresponding aziridine inthe yields of 61-95%. |
Multi-step reaction with 2 steps 1: iodine; triphenylphosphine; 1H-imidazole / acetonitrile; diethyl ether / 12 h / 0 - 20 °C 2: ferric(III) bromide; 1,10-Phenanthroline / acetonitrile / 0.5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; silver trifluoromethanesulfonate In dichloromethane at 25℃; for 1h; Inert atmosphere; Schlenk technique; Overall yield = 65 %; Overall yield = 62 mg; stereoselective reaction; | ||
With toluene-4-sulfonic acid; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane; water at 25℃; for 4h; Inert atmosphere; Schlenk technique; Overall yield = 58 %; Overall yield = 61 mg; | 4.2. PhI(OCOCF3)2 Mediated synthesis of oxazolidines 3ae-3ag: Method A General procedure: 4.2.1. General procedure for the PhI(OCOCF3)2 mediated synthesis of oxazolidines 3ae3ag: Method A. To a colorless solution of corresponding N-Ts aminoalcohol (0.33 mmol) and styrene (0.36 mmol) in CH2Cl2 (3 mL) in a well dried Schlenk flask under argon atmosphere was added PhI(OCOCF3)2 (0.50 mmol) and PTSA*H2O (0.36 mmol) at room temperature [25 °C]. The progress of the reaction was monitored by TLC. After stirring the reaction mixture for 4 h at room temperature 5 mL of satd soln of aq NaHCO3 was added and extracted with CH2Cl2. The combined organic layers were dried (anhyd. Na2SO4), filtered and concentrated in vacuo. The crude product obtained was purified by flash chromatography (pet. ether : Et2O, 8:1) to furnish oxazolidines in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Stage #1: N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-benzenesulfonamide With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: methyl (2E,4E)-6-bromo-2,4-hexadienoate In tetrahydrofuran; mineral oil at 20℃; for 20h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; water at 20℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; | |
66% | With potassium carbonate; potassium iodide In acetone at 60℃; | |
With potassium carbonate In acetone Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | |
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; | ||
With triethylamine In dichloromethane at 0 - 20℃; for 2h; |
With triethylamine In dichloromethane at 0 - 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate In acetone at 85℃; for 12h; Inert atmosphere; | |
99% | With potassium carbonate In acetone for 12h; Schlenk technique; Inert atmosphere; Heating; | |
With potassium carbonate In acetone for 2h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium carbonate; potassium iodide In acetone for 16h; Reflux; | |
45% | With potassium carbonate; potassium iodide In acetone at 60℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With (triphenylphosphine)gold(I) chloride; 1-(trifluoromethanesulfonyloxy)-1,2-benziodoxol-3(1H)-one In acetonitrile at 50℃; for 18h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0℃; for 3h; Inert atmosphere; | |
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 0 - 20℃; for 12h; | Typical procedure for the synthesis of starting materials General procedure: Iodination: To a solution of triphenylphosphine (1.97 g, 7.5 mmol, 3.0 equiv) and imidazole (0.58 g, 8.5 mmol, 3.4 equiv) in Et2O:CH3CN = 3:1 (25 mL) was added I2 (1.90 g, 7.5 mmol, 3.0 equiv) slowly at 0 oC. After stirred for 30 minutes, add N-tosylated alcohol (2.5 mmol) to the solution dropwise. The mixture was stirred for 12 hours at room temperature. Check the progress of the reaction by TLC, the reaction mixture was quenched with saturated NH4Cl aqueous solution and extracted by CH2Cl2. The organic layer was dried over MgSO4 and concentrated under the vacuum. Flash column chromatography provided the iodinated products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: buta-1,3-diene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: 2,3-dimethyl-buta-1,3-diene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: 6,7-epoxymyrcene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: buta-1,3-dien-1-ylbenzene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: p-methoxyphenylbutadiene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With copper diacetate; palladium diacetate In dimethyl sulfoxide at 20℃; for 0.25h; Sealed tube; Stage #2: 1-bromo-4-(buta-1,3-dienyl)benzene With oxygen In dimethyl sulfoxide at 80℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate In acetone at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With silver trifluoromethanesulfonate In neat (no solvent) at 20℃; for 10h; Inert atmosphere; stereoselective reaction; | |
98 % ee | With silver trifluoromethanesulfonate In neat (no solvent) at 20℃; for 10h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 3h; | General procedure for oxidation of alcohols General procedure: To a solution of primary alcohol in anhydrous DCM was added Dess-Martin periodinane(1.5 equiv) at 0 °C. After being stirred at room temperature for 3 h, the mixture wastreated with saturated aqueous Na2SO3 and NaHCO3. The aqueous layer was extractedwith EtOAc twice. The combined organic layers were washed with brine, dried overMgSO4, and concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford aldehyde. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate In toluene at 80℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With bis(η3-allyl-μ-chloropalladium(II)); Methyl formate; triethylamine; bis[2-(diphenylphosphino)phenyl] ether In water; toluene at 45℃; for 21h; Sealed tube; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With caesium carbonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 1-(1-(4-methoxyphenyl)vinyl)tetrahydro-1H-thiophen-1-ium triflate In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With zinc(II) bis(tetrafluoroborate) hydrate; [bis(acetoxy)iodo]benzene In toluene at 20℃; for 12h; Schlenk technique; |
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