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CAS No. : | 768-93-4 | MDL No. : | MFCD00134444 |
Formula : | C10H15I | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PXVOATXCSSPUEM-UHFFFAOYSA-N |
M.W : | 262.13 | Pubchem ID : | 136609 |
Synonyms : |
|
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 |
---|---|---|
89% | With iodine; triphenylphosphine; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 20℃; for 4h; | General procedure: To a stirred solution of triphenylphosphine (1.5 mmol) in dry dichloromethane was added iodine (1.5 mmol)and polymer supported 4-DMAP (0.4 mmol, 40 mol%). Stirring was continued for 2 min; alcohol (1mmol) was then added. The reaction was monitored by TLC. After complete conversion of the alcohol (as indicated byTLC), the reaction was quenched with an aqueous solution of sodium thiosulfate (20 mL). The organic solventswere removed and the aqueous solution extracted with ethylacetate (50 mL). The combined organic layers weredried using sodium sulfate (anhydrous), filtered and concentrated. The residue was purified by column chromatography (2% EtOAc in hexane) to get the desired iodide product. |
88%Chromat. | With phosphorus pentoxide; potassium iodide; In acetonitrile; at 45℃; for 2h; | General procedure: To a mixture of alcohol (1.0 mmol) and KI (1.5 mmol, 0.25 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction stirred at room temperature for the time specified in Table 2. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with an aqueous solution of Na2S2O3 (10%, 10 mL), water (10 mL), and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With nitrosonium tetrafluoroborate at 0℃; for 1.5h; | |
87% | With iodine pentoxide at 40 - 50℃; for 0.5h; | |
With nitronium tetrafluoborate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: Preparation of 1-adamantylzinc bromide (A): In an oven-dried 250 mL round-bottomed flask equipped with a stir bar was added 6.54 g of active zinc (Zn*,100.0 mmol) in 100 mL of THF. Next, 1-bromoadamantane (10.5 g, 50.0 mmol) was cannulated into the flask at room temperature. The resulting mixture was then allowed to reflux for 2 h. The solution was cooled to room temperature and settled down. Then the supernatant was used for the subsequent coupling reactions. Preparation of adamantan-1-yl-(4-methoxyphenyl)methanone (1c): Into a 25 mL round-bottomed flask were placed CuCN (0.02 g, 10 mol %) and LiCl (0.02 g, 20 mol %). The flask was pumped down and recharged with argon gas. Then, 2.0 mL of THF was added to dissolve. The flask was cooled to 0 C using an ice-bath. 4-Methoxybenzoyl chloride (0.24 g, 1.4 mmol) dissolved in 2.0 mL of THF was added into the flask. Next, 4.0 mL of 1-adamantylzinc bromide (0.5M in THF, 2.0 mmol) was cannulated into the flask under argon atmosphere at 0 C, then the whole mixture was allowed to warm up gradually to room temperature over 3 h while being stirred. Quenched with saturated 3M HCl solution, then extracted with ethyl ether (10 mL × 3). Washed with saturated NaHCO3, 8% NH4OH solutions, and brine, then dried over anhydrous MgSO4. Purification by flash column chromatography (hexanes/ethyl acetate) afforded 0.16 g of 1c in 42% isolated yield as a pale yellow solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 70% 2: 69% 3: 7% | With 2,4,6-triphenylverdazyl radical at 50℃; for 960h; sealed tube; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With iodine pentoxide In 1,4-dioxane at 90 - 95℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium hydroxide; In water; acetonitrile; at 35℃; under 300030.0 Torr;Autoclave; UV-irradiation; Inert atmosphere;Product distribution / selectivity; | Example 1; Precursors and Resultant Products; Precursors that were used to label acids are shown in List. 1. List 1. Iodides used as precursors in the synthesis of labeled acids The following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [11C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds.; Example 3; Preparation of [carboxyl-11C] acids; General procedure.; An iodide (100 mumol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 muL). Water (100 muL) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 muL), pre-charged with [11C]carbon monoxide (10-8-10-9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35 C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction. |
77%Chromat. | With potassium hydroxide; water; In acetonitrile; at 35℃; under 300030.0 Torr; for 0.0833333 - 0.116667h;UV-irradiation;Product distribution / selectivity; | .Example 1; - Precursors and Resultant ProductsPrecursors that were used to label acids are shown in List. 1.2-Iodo-propaneIodo-cyclohexane1-Iodo-butane4-(3-Iodo-prorhoyl)-rhohenol12-Iodo-2-methyl-propane5-Iodo-rhoent-l-eneIodododecane EPO <DP n="26"/>11-Iodo-undecanoic acid1 -Iodo-adamantaneList 1. Iodides used as precursors in the synthesis of labeled acidsThe following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [l C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds. Table 1 Radiochemical yields for l ^-labelled acidsAdditiveEntry Labelled compounda Solvents c [on CvJ. Y f0/ieLambdald* Y.i0el,lfd d (mmol)J .0TEtaF/H2O (4:1) TBAOH (0.03) 82+2 80+2 70+2OHACN/H2O (3:2) KOH (0.04) 84+/-1 81+1 67+/-4THFZH2O (4:1) TBAOH (0.03) 81+3 74+2 59+/-74a THF/H2O (4:1) KOH (0.04) 79 68 51 4b THF/H2O (4:1) 73+5 62+5 <1 EPO <DP n="27"/>O7 THFVH2O (4:1) TBAOH (0.03) 36 d - v/?vOH8 THFZH2O (4:1) TBAOH (0.03) 82+2 73+2 55+49a THFZH2O (9:1) TBAOH (0.03) 82 68 52 THFZacetoneZH2O 9b (3:1:1) 91+4 82+4 65+410a THFZH2O (4:1) TBAOH (0.13) 84 76 10b THFZH2O (4:1) 37 34 - ACNZH2O (4:1) KOH (0.1) 81+6 77+5 63+4 ACNZH2O (9:1) TBAOH (0.2) 94 56 33 THFZH2O (9:1) TBAOH (0.15) 90 64 55The position of C label is denoted by an asterisk. Decay-corrected radiochemical yield determined by LC. Number of runs. d Unseparated peaks; Example 3 - Preparation Qf FCaJrOoXKZ-11Cl acidsGeneral procedure. An iodide (100 /rniol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 //L). Water (100 //L) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 //L), pre-charged with [?C]carbon monoxide (10"8 -10'9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the EPO <DP n="29"/>semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.(l-13C)4-Phenylbutyric acid was synthesised from (3-iodopropyl)benzene as described in the general procedure. (13C)Carbon monoxide (approximately 0.05 mmol) was added to [nC]carbon monoxide and the reaction was run for 1 h. 1H NMR (400MHz, CDCl3): delta 10.0 (br s, IH), 7.35-7.18 (m, 5H), 2.70 (m, 2H), 2.41 (m, 2JH13C=7.3HZ, 2H), 2.00 (m, 3JH13C=4.4HZ, 2H). 13C NMR (100MHZ, CDCl3): delta 180.5, 141.2, 128.5, 128.4, 126.0, 34.9 (d, 2J13c13c =3.8Hz), 33.0 (d, 1J13C13C=SSJHz), 26.2. |
56%Chromat. | With tetra(n-butyl)ammonium hydroxide; water; In acetonitrile; at 35℃; under 300030.0 Torr; for 0.0833333 - 0.116667h;UV-irradiation;Product distribution / selectivity; | .Example 1; - Precursors and Resultant ProductsPrecursors that were used to label acids are shown in List. 1.2-Iodo-propaneIodo-cyclohexane1-Iodo-butane4-(3-Iodo-prorhoyl)-rhohenol12-Iodo-2-methyl-propane5-Iodo-rhoent-l-eneIodododecane EPO <DP n="26"/>11-Iodo-undecanoic acid1 -Iodo-adamantaneList 1. Iodides used as precursors in the synthesis of labeled acidsThe following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [l C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds. Table 1 Radiochemical yields for l ^-labelled acidsAdditiveEntry Labelled compounda Solvents c [on CvJ. Y f0/ieLambdald* Y.i0el,lfd d (mmol)J .0TEtaF/H2O (4:1) TBAOH (0.03) 82+2 80+2 70+2OHACN/H2O (3:2) KOH (0.04) 84+/-1 81+1 67+/-4THFZH2O (4:1) TBAOH (0.03) 81+3 74+2 59+/-74a THF/H2O (4:1) KOH (0.04) 79 68 51 4b THF/H2O (4:1) 73+5 62+5 <1 EPO <DP n="27"/>O7 THFVH2O (4:1) TBAOH (0.03) 36 d - v/?vOH8 THFZH2O (4:1) TBAOH (0.03) 82+2 73+2 55+49a THFZH2O (9:1) TBAOH (0.03) 82 68 52 THFZacetoneZH2O 9b (3:1:1) 91+4 82+4 65+410a THFZH2O (4:1) TBAOH (0.13) 84 76 10b THFZH2O (4:1) 37 34 - ACNZH2O (4:1) KOH (0.1) 81+6 77+5 63+4 ACNZH2O (9:1) TBAOH (0.2) 94 56 33 THFZH2O (9:1) TBAOH (0.15) 90 64 55The position of C label is denoted by an asterisk. Decay-corrected radiochemical yield determined by LC. Number of runs. d Unseparated peaks; Example 3 - Preparation Qf FCaJrOoXKZ-11Cl acidsGeneral procedure. An iodide (100 /rniol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 //L). Water (100 //L) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 //L), pre-charged with [?C]carbon monoxide (10"8 -10'9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the EPO <DP n="29"/>semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.(l-13C)4-Phenylbutyric acid was synthesised from (3-iodopropyl)benzene as described in the general procedure. (13C)Carbon monoxide (approximately 0.05 mmol) was added to [nC]carbon monoxide and the reaction was run for 1 h. 1H NMR (400MHz, CDCl3): delta 10.0 (br s, IH), 7.35-7.18 (m, 5H), 2.70 (m, 2H), 2.41 (m, 2JH13C=7.3HZ, 2H), 2.00 (m, 3JH13C=4.4HZ, 2H). 13C NMR (100MHZ, CDCl3): delta 180.5, 141.2, 128.5, 128.4, 126.0, 34.9 (d, 2J13c13c =3.8Hz), 33.0 (d, 1J13C13C=SSJHz), 26.2. |
64%Chromat. | With tetra(n-butyl)ammonium hydroxide; water; In tetrahydrofuran; at 35℃; under 300030.0 Torr; for 0.0833333 - 0.116667h;UV-irradiation;Product distribution / selectivity; | .Example 1; - Precursors and Resultant ProductsPrecursors that were used to label acids are shown in List. 1.2-Iodo-propaneIodo-cyclohexane1-Iodo-butane4-(3-Iodo-prorhoyl)-rhohenol12-Iodo-2-methyl-propane5-Iodo-rhoent-l-eneIodododecane EPO <DP n="26"/>11-Iodo-undecanoic acid1 -Iodo-adamantaneList 1. Iodides used as precursors in the synthesis of labeled acidsThe following experiments illustrate the present invention. Radical carboxylation using submicromolar amounts of [l C]carbon monoxide is performed yielding labeled with the acids shown in Table 1 as target compounds. Table 1 Radiochemical yields for l ^-labelled acidsAdditiveEntry Labelled compounda Solvents c [on CvJ. Y f0/ieLambdald* Y.i0el,lfd d (mmol)J .0TEtaF/H2O (4:1) TBAOH (0.03) 82+2 80+2 70+2OHACN/H2O (3:2) KOH (0.04) 84+/-1 81+1 67+/-4THFZH2O (4:1) TBAOH (0.03) 81+3 74+2 59+/-74a THF/H2O (4:1) KOH (0.04) 79 68 51 4b THF/H2O (4:1) 73+5 62+5 <1 EPO <DP n="27"/>O7 THFVH2O (4:1) TBAOH (0.03) 36 d - v/?vOH8 THFZH2O (4:1) TBAOH (0.03) 82+2 73+2 55+49a THFZH2O (9:1) TBAOH (0.03) 82 68 52 THFZacetoneZH2O 9b (3:1:1) 91+4 82+4 65+410a THFZH2O (4:1) TBAOH (0.13) 84 76 10b THFZH2O (4:1) 37 34 - ACNZH2O (4:1) KOH (0.1) 81+6 77+5 63+4 ACNZH2O (9:1) TBAOH (0.2) 94 56 33 THFZH2O (9:1) TBAOH (0.15) 90 64 55The position of C label is denoted by an asterisk. Decay-corrected radiochemical yield determined by LC. Number of runs. d Unseparated peaks; Example 3 - Preparation Qf FCaJrOoXKZ-11Cl acidsGeneral procedure. An iodide (100 /rniol) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove oxygen) and dissolved in THF (400 //L). Water (100 //L) and an optional additive were added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the micro-autoclave (270 //L), pre-charged with [?C]carbon monoxide (10"8 -10'9 mol) mixed with He. The mixture was irradiated with a UV source for 5-7 min with stirring at 35C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the EPO <DP n="29"/>semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fraction.(l-13C)4-Phenylbutyric acid was synthesised from (3-iodopropyl)benzene as described in the general procedure. (13C)Carbon monoxide (approximately 0.05 mmol) was added to [nC]carbon monoxide and the reaction was run for 1 h. 1H NMR (400MHz, CDCl3): delta 10.0 (br s, IH), 7.35-7.18 (m, 5H), 2.70 (m, 2H), 2.41 (m, 2JH13C=7.3HZ, 2H), 2.00 (m, 3JH13C=4.4HZ, 2H). 13C NMR (100MHZ, CDCl3): delta 180.5, 141.2, 128.5, 128.4, 126.0, 34.9 (d, 2J13c13c =3.8Hz), 33.0 (d, 1J13C13C=SSJHz), 26.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triethyl borane; oxygen; ytterbium(III) triflate In tetrahydrofuran; hexane; dichloromethane at -78℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dicyclohexylcarbodiimide / CH2Cl2 2: CF3CH2I / benzene / Heating; Irradiation 3: Me3SnLi / tetrahydrofuran / 0.5 h / Ambient temperature; other (trimethylstannyl)alkali reagent; also in the presence of tert-butylamine or dicyclohexylphosphine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | General procedure: An alcohol (200 muoaol) and appropriate base (Table 1) was placed in a capped vial (1 mL, flushed beforehand with nitrogen to remove air) and dissolved in THF (500 //L); in some cases the alcohol was used as a solvent instead of THF. An iodide (100 //mol) was added to the solution ca. 7 min before the start of the synthesis. The resulting mixture was pressurized (over 40 MPa) into the autoclave, pre-charged with [?C]carbon monoxide (10~8 -10"9 mol) and helium gas mixture. The mixture was irradiated with the Xe-Hg lamp for 6 min with stirring at 350C. The crude reaction mixture was then transferred from the autoclave to a capped vial, held under reduced pressure. After measurement of the radioactivity the vial was purged with nitrogen and the radioactivity was measured again. The crude product was diluted with acetonitrile or methanol (0.6 mL) and injected on the semi-preparative LC. Analytical LC and LC-MS were used to assess the identity and radiochemical purity of the collected fractions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81%Chromat. | With 2,2'-azobis-(2,4-dimethylvaleronitrile); sodium cyanoborohydride; In ethanol; at 70℃; for 0.166667h;Automated synthesizer; Flow reactor; | General procedure: A 50 mL EtOH solution of 1a (10 mmol, 2.4 g, 0.2 M), ethyl acrylate (16 mmol, 1.6 g, 1.6 equiv), V-65 (1 mmol, 248.3 mg, 10 mol %), and decane as an internal standard (400 mg) (solution A), and a 50 mL EtOH solution of NaBH3CN (30 mmol, 1.87 g, 3 equiv) (solution B) were prepared and placed in bottles A and B respectively. These two bottles were connected by PTFE tube to the automated microflow system, MiChS system X-1, equipped with a micromixer (MiChS -150, 150 m), a residence time unit (RTU, 1 mm i.d. and 3 m length) and an automated fraction collector. Four different conditions (residence time = 5, 10, 15, and 20 min at 70 C, relative flow rate: A:B = 1:1) were inputted through a touch panel and the program was run. The reaction mixtures for each condition were sampled (1 mL) automatically in vials containing 1 mL of H2O by a fraction collector. Products were extracted with Et2O (1 mL), and the yields were determined by GC analysis equipped with a flame ionization detector. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: To a stirred solution of O-triphenylsilyl oxime (0.25 mmol) and t-butyl iodide (368 mg, 2.0 mmol) in toluene at 90 C was added triethyl borane (1.25 mL, 1.0 M solution in hexane, 1.25 mmol) under air atmosphere. The resulting mixture was stirred until the starting material was consumed. The reaction mixture was washed with saturated sodium bicarbonate solution, and the product was extracted into ethyl acetate. The organic layer was dried over MgSO4 and was evaporated under reduced pressure to afford a residue, which was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimanganese decacarbonyl; trifluoroacetic acid In methanol at 28℃; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.2% | With sodium hydroxide; In dichloromethane; at 90℃; for 24h;pH 10 - 11;Autoclave; | Weigh 76.5 g (0.8 mol) of trimethylamine hydrochloride into a three-necked flask containing 180 g of dichloroethane and cool it on an ice bath (to prevent sodium hydroxide from adding too fast, neutralize the heat so that the temperature of the solution is too high. Trimethylamine escaped), alkalinized by addition of sodium hydroxide to pH=10-11 with stirring, and filtered. The resulting trimethylamine dichloroethane solution was poured into a 250 mL autoclave, and 26.2 g (0.1 mol) of <strong>[768-93-4]1-iodoadamantane</strong> was added and the system was closed. The reaction was continued while heating to 90 C. for 24 hours. The reaction is over,The reaction solution was cooled to room temperature, filtered and washed with acetone to give 29.6 g of white N,N,N-trimethyl-1-adamantyl ammonium iodide in a yield of 92.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.3% | In ethyl acetate; at 90℃; for 36h;Autoclave; | In a 250 mL autoclave, add 26.2 g (0.1 mol)<strong>[768-93-4]1-iodoadamantane</strong> and 120 g of ethyl acetate, 29.5 g (0.5 mol) of trimethylamine gas was introduced into the above solution within 30 minutes, and the system was closed.After heating to 90C, the reaction was continued for 36 hours; at the end of the reaction, the reaction solution was cooled to room temperature, filtered and washed with cyclohexane to give white N,N,N-trimethyl-1-adamantyl ammonium iodide 29.0 g. Yield 90.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triethyl borane; diphenylsilane; ytterbium(III) triflate; In tetrahydrofuran; 1,2-dichloro-ethane; at 20℃; for 24h;Green chemistry; | General procedure: A solution of triethylborane (0.25mL, 0.25mmol, 1M solution in THF) was added to a solution of aldehyde (0.50mmol), benzhydrazide (0.50mmol, 78mg), diphenylsilane (0.50mmol, 0.09mL), and alkyl halide (15mmol) in the presence of Yb(OTf)3 (0.125mmol, 77.5mg) in (ClCH2)2/THF (v/v, 1:1) (5 mL) at room temperature. Further triethylborane (0.25mL, 1M solution in THF) was added every 4h and air was injected through a needle fixed directly above the solution until the entire starting material was consumed (as monitored by TLC). When the reaction was complete, the mixture was treated with saturated aqueous NaHCO3 (5mL). The aqueous phase was extracted with CH2Cl2 twice, and the organic layer was washed with brine and dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) bromide dimethoxyethane; 1,1,1,3',3',3'-hexafluoro-propanol; zinc; In tetrahydrofuran; at 25℃; for 12h;Inert atmosphere; | General procedure: A 2 mL crimp-top GC vial was charged with NiBr2(DME) (6.2 mg, 0.02 mmol, 0.1 equiv), dppf (11 mg, 0.02 mmol, 0.1 equiv), and activated Zn powder [35] (26.2 mg, 0.4 mmol, 2 equiv). The vial was crimped shut and the olefin (0.2 mmol, 1 equiv) was injected through the septum as a solution in 0.3 mL THF followed by 0.2 mL HFIP. The iodide (1-2 equiv) was then added (as a solution in THF, if solid) and the vial was shaken at 1000 rpm for 12 h at 25 C. The reaction was diluted with EtOAc and quenched by the addition of 1 M HCl (aq). The aqueous phase was extracted with three portionsof EtOAc. The combined organic phase was then passed through a plug of silica. An aliquot of the organic phase was used for GC or GC/MS analysis with mesitylene as an internal standard. Solvent was removed and the mixture was purified by chromatography on silicagel with EtOAc/hexane as the eluent to give the products as colorless oils. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In benzonitrile; at 145℃; for 24h; | To a solution of 4- (1-azepanyl) pyridine (3.52 g, 20.0 mmol) in benzonitrile (6.0 mL) was added <strong>[768-93-4]1-iodoadamantane</strong> (5.77 g, 22.0 mmol).Stirred at 145 C. for 24 hours. After cooling to room temperature,Benzonitrile is distilled off from the reaction solution,The obtained viscous liquid was purified by silica column chromatography (chloroform / methanol),Red-brown solid 1- (1-adamantyl) -4- (1-azepanyl) pyridinium iodide(7.55 g, 86% yield) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In benzonitrile; at 145℃; for 24h; | 4- [Bis (2-ethoxyethyl) amino] pyridine (0.715 g, 3.00 mmol) in benzonitrile (1.0 mL)To the solution was added <strong>[768-93-4]1-iodoadamantane</strong> (0.865 g, 3.30 mmol), and the mixture was stirred at 145 C for 16 hours.After cooling to room temperature, the reaction solution was purified by silica column chromatography (chloroform / methanol),Viscous liquid 1- (1-adamantyl) -4- [bis (2-ethoxyethyl) amino] pyridinium iodide(1.50 g, quantitative). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In benzonitrile; at 145℃; for 20h; | <strong>[768-93-4]1-iodoadamantane</strong> (0.865 g, 3.30 mmol) was added to a solution of 4-diphenylaminopyridine (0.739 g, 3.00 mmol) in benzonitrile (1.0 mL).Was added and stirred at 145 C. for 20 hours. After cooling to room temperature,The reaction solution was purified by silica column chromatography (chloroform / methanol),1- (1-adamantyl) -4-diphenylaminopyridinium iodide as a white solid(1.44 g, 94% yield) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | General procedure: Alkyl iodide (8.9 mmol) was added to a suspension of alpha-ketoester-derived hydrazone (0.45 mmol) ??on-water? (5 mL). The reaction mixture was purged with argon for 10 min. Triethylborane solution (220 muL, 0.22 mmol, 1 M solution in hexanes) was added every 3 h until the reaction was complete and a needle was placed just above the suspension to supply air. After completion of the reaction, saturated aqueous NH4Cl solution was added and the reaction mixture was extracted with CH2Cl2. The organic layer was evaporated and purified by flash column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dimanganese decacarbonyl In dichloromethane at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; [Ir(3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl)2(4,4'-bis(trifluoromethyl)bipyridine)]PF6; water; bis(2,2,6,6-tetramethyl-3,5-heptadionato) copper(II); lithium tert-butoxide; In acetonitrile; at 20℃; for 4h;Irradiation; Sealed tube; | General procedure: To an oven-dried 8 mL vial equippedwith a Teflon stir bar was added N-nucleophile (0.05 mmol, 1.0 equiv.), Ir[dF(CF3)ppy]2[4,4¢-d(CF3)bpy]PF6 ([Ir-1], 0.4 μmol, 0.008 equiv.), copper salt (0.01 mmol, 0.2 equiv.), base (0.15 mmol, 3.0equiv.) and solvent (0.5 mL, 0.1 M). The resulting solution was stirred for 1-2 minutes under air to ensurecomplete ligation of the nucleophile to the copper precatalyst. Following this complexation period, alkylhalide (0.125 mmol, 2.5 equiv.), silyl radical precursor (0.125 mmol, 2.5 equiv.) and any further additives,such as H2O (9 μL, 0.5 mmol, 10 equiv.), were added to the mixture as indicated, after which the vial wascapped and an 18G vent needle was inserted through the Teflon-lined septum. Alternatively, for nonaerobicreactions employing stoichiometric oxidants, oxidant (0.10 mmol, 2.0 equiv.) was added last, afterwhich the vial was capped, sparged under nitrogen for 10 minutes and sealed with Parafilm. Forirradiated experiments, the reaction mixture was subsequently stirred within the Integrated Photoreactor(450 nm irradiation) for 4 hours using the following settings (unless otherwise specified): 25% LEDintensity, 100 rpm stir rate and 3500 rpm fan speed. Alternatively, for select indicated examples, the vialwas irradiated using a single 40 W Kessil blue LED for 4 hours (vial placed 2 cm away), using fans tomaintain equilibrated temperatures of ~30 C. After 4 hours, mesitylene (5 μL, 35.9 μmol, 0.72 equiv.)was added via syringe to the reaction mixture, which was stirred for an additional 1-2 minutes. An aliquotof the reaction mixture (~0.1 mL) was passed through a celite plug into an NMR tube, followed by 0.5-0.8mL CDCl3, and analyzed via 1H NMR to determine the analytical yield of the desired N-alkylated product.Deviations to the general protocol described above, as well as specific reagent identities andstoichiometries used during optimization, are indicated within each experiment below. |
[ 87621-26-9 ]
1-Iodo-3,5-dimethylcyclohexane
Similarity: 0.94
[ 126416-20-4 ]
3,3'-Diiodo-1,1'-bi(bicyclo[1.1.1]pentane)
Similarity: 0.83
[ 87621-26-9 ]
1-Iodo-3,5-dimethylcyclohexane
Similarity: 0.94
[ 126416-20-4 ]
3,3'-Diiodo-1,1'-bi(bicyclo[1.1.1]pentane)
Similarity: 0.83
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H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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