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CAS No. : | 1112-54-5 | MDL No. : | MFCD00041345 |
Formula : | C8H18Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HBWGDHDXAMFADB-UHFFFAOYSA-N |
M.W : | 142.31 | Pubchem ID : | 559195 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.96 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.97 cm/s |
Log Po/w (iLOGP) : | 2.85 |
Log Po/w (XLOGP3) : | 4.5 |
Log Po/w (WLOGP) : | 3.22 |
Log Po/w (MLOGP) : | 3.15 |
Log Po/w (SILICOS-IT) : | 1.28 |
Consensus Log Po/w : | 3.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.29 |
Solubility : | 0.0724 mg/ml ; 0.000509 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.22 |
Solubility : | 0.00856 mg/ml ; 0.0000601 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.78 |
Solubility : | 0.236 mg/ml ; 0.00166 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.89 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P233-P240-P241-P242-P243-P260-P261-P264-P271-P280-P302+P352-P303+P361+P353-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P370+P378-P403-P403+P233-P403+P235-P405-P501 | UN#: | 1993 |
Hazard Statements: | H225-H315-H319-H335 | Packing Group: | Ⅲ |
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% | With Na In diethyl ether | |
With sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 25 % Chromat. 2: 65 % Chromat. | With dodecacarbonyl-triangulo-triruthenium In benzene at 50℃; for 5h; | |
With [ReCl2(NO)(PCy3)2(CH3CN)] In (2)H8-toluene at 100℃; for 24h; Inert atmosphere; | ||
1: 10 %Chromat. 2: 90 %Chromat. | With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); carbon dioxide; bis(dicyclohexylphosphino)methane In toluene for 16h; Autoclave; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 24h; | |
87% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In benzene at 100℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 26 % Chromat. 2: 2 % Chromat. 3: 2 % Chromat. 4: 68 % Chromat. | With oxygen In benzene at 130℃; for 6h; effects of various catalysts, pressures; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene for 20h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With [Rh(cod)][BPh4]; hydrogen In toluene at 120℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium acetate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With hydrogenchloride In 1,4-dioxane; chloroform at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: PCl5; chlorine 2: aqueous KOH / 145 °C | ||
Multi-step reaction with 2 steps 1: PCl5; chlorine 2: aqueous KOH / 145 °C | ||
Multi-step reaction with 2 steps 1: neat (no solvent) 2: KOH / ethanol |
Multi-step reaction with 2 steps 1: Br2 / not given 2: KOH / ethanol; potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20 - 36 %Chromat. 2: 7 - 9 %Chromat. 3: 12 - 14 %Chromat. | In toluene at 40℃; for 1h; | 1; 2 Example 1 In a reactor were placed triethylsilane (Et3SiH) (5 mmol), di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [IrCl(cod)]2 (0.05 mmol), vinyl acetate (20 mmol), and toluene (3 ml), and a reaction was conducted at 40° C. in a nitrogen atmosphere for one hour. After the reaction, the reaction mixture was analyzed by gas chromatography to find that vinyltriethylsilane was produced in a yield of 20%, and tetraethylsilane and acetic ester of triethylsilanol were by-produced in yields of 9% and 14%, respectively. Example 2; In a reactor were placed di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [IrCl(cod)]2 (0.05 mmol), vinyl acetate (20 mmol), and toluene (3 ml). The mixture was raised in temperature to 40° C. in a nitrogen atmosphere, triethylsilane (Et3SiH) (5 mmol) was added thereto over one hour, and a reaction was carried out at 40° C. for one hour. After the reaction, the reaction mixture was analyzed by gas chromatography to find that vinyltriethylsilane was produced in a yield of 36% and tetraethylsilane and acetic ester of triethylsilanol were by-produced in yields of 7% and 12%, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In diethyl ether N2-atmosphere; stirring (room temp., 4 h); evapn. (0.1 Torr), hexane addn., filtering, evapn.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cis-dibromo(η2-dihydrogen)(nitrosyl)-trans-bis(triisopropylphosphane)rhenium In (2)H8-toluene at 100℃; for 24h; Inert atmosphere; chemoselective reaction; | ||
With Re(Br)2(NO)(MeCN)2(PiPr3) In benzene at 70℃; for 7h; Inert atmosphere; | ||
With anti-[Cp*Fe-(2,6-diethyl-4,8-dimethyl-s-indaceneiide)-Rh(COD)] In toluene at 80℃; for 1.66667h; Inert atmosphere; | 2.1 General procedure for the dehydrogenative silylation of styrene General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with the catalytic amount of complex (0.015mmol). The reactor was evacuated and filled with dinitrogen. Styrene (0.52mL, 4.5mmol) and toluene (5mL) were added, and the mixture was stirred for 5min. Then Et3SiH (0.24mL, 1.5mmol) was added. The reaction flask was immersed in an 80°C thermo-stabilized bath. The progress of the reaction was monitored by GC (disappearance of Et3SiH). The products were identified by 1H NMR, by GC-MS, and by comparison with the literature data [28]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,1,1,2,2,2-hexamethyldisilane; P(p-C6H4F)3 In ethyl-cyclohexane at 130℃; for 30h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,1,1,2,2,2-hexamethyldisilane; P(p-C6H4F)3 In ethyl-cyclohexane at 130℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HBr / not given 2: not given |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | RuH2(CO)(PPh3)3; at 145℃; for 50h;Inert atmosphere; Schlenk tube; | A 10 mL Schlenk tube and a TeflonR-coated magnetic stirrer were placed in a drying oven and heated. After adequate heating, they were removed from the drying oven and the magnetic stirrer was placed in the Schlenk tube. The interior of the Schlenk tube was then exchanged with reduced-pressure nitrogen. After the Schlenk tube was cooled to room temperature, <strong>[3029-32-1]pentacene-6,13-dione</strong> (0.5 mmol, 154.1 mg) and a RuH2(CO)(PPh3)3 complex (0.10 mmol, 91.9 mg) were added. After then exchanging the interior of the Schlenk tube with reduced-pressure nitrogen, toluene (1.0 mL) and triethylvinylsilane (5.0 mmol, 920 mL) were added. The Schlenk tube was subsequently heated in an oil bath (145C) and the interior mixture was reacted for 50 hours, after which the product was isolated. Isolation of the product was accomplished by purification using gel permeation chromatography (eluent = CHCl3). As a result, 5,7,12,14-tetrakis(2-(triethylsilyl)ethyl)<strong>[3029-32-1]pentacene-6,13-dione</strong> was obtained at a 56% yield. The 1H-NMR, 13C-NMR, IR and APCI-HRMS measurement results and the melting point for the obtained product were as follows. 1H NMR (CDCl3):delta 0.749 (q, 24H, J = 7.8 Hz, SiCH2CH3), 1.045-1.115 (m, 44H,CH3 and ArCH2CH2Si), 3.30-3.50 (m, 8H,ArCH2), 7.632 (dd, 4H, J = 3.4,6.3 Hz, ArH), 8.206 (dd, 4H, J = 3.4,6.3 Hz, ArH) 13C NMR CDCl3):delta 3.424, 7.648, 15.259, 23.297, 126.133, 127.637, 131.467, 133.423, 141.231, 192.583 IR (KBr):3081 w, 2952 s, 2908 s, 2874 s, 2805 w, 2730 w, 1672 s, 1613 w, 1566 w, 1507 w, 1457 w, 1438 w, 1415 w, 1391 m, 1358 w, 1341 w, 1312 w, 1278 m, 1226 m, 1179 w, 1169 w, 1144 w, 1098 m, 1046 w, 1005 m, 833 w, 798 w, 771 m, 756 s, 735 s, 562 w cm-1 APCI-HRMS (+): Calculated for C54H85O2Si4 (M+H)+ 877.56266, Found: 877.56130. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 89% 2: 1% | With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In para-xylene at 140℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; | 4.3.2 Typical procedure for ruthenium-catalyzed alkylation of o-acylanilines with olefins: ruthenium-catalyzed deamination/alkylation of 2a with 4a General procedure: To a 10mL Schlenk tube were added in a glove box o-acylaniline 2a (41.5mg, 0.2mmol), RuH2(CO)(PPh3)3 (1) (36.7mg, 0.04mmol), olefin 4a (0.045mL, 0.3mmol), and p-xylene (0.3mL), and the mixture was heated for 24h in an oil bath whose temperature adjusted to 140°C. After the reaction, n-eicosane (0.1mmol) was added as an internal standard to the resulting mixture, which was then analyzed by GC. Column chromatography of the crude material (100:1 hexane/EtOAc) afforded 5a as pale yellow oil (43.1mg, 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 34% 2: 1% | With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In para-xylene at 140℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; | 4.3.2 Typical procedure for ruthenium-catalyzed alkylation of o-acylanilines with olefins: ruthenium-catalyzed deamination/alkylation of 2a with 4a General procedure: To a 10mL Schlenk tube were added in a glove box o-acylaniline 2a (41.5mg, 0.2mmol), RuH2(CO)(PPh3)3 (1) (36.7mg, 0.04mmol), olefin 4a (0.045mL, 0.3mmol), and p-xylene (0.3mL), and the mixture was heated for 24h in an oil bath whose temperature adjusted to 140°C. After the reaction, n-eicosane (0.1mmol) was added as an internal standard to the resulting mixture, which was then analyzed by GC. Column chromatography of the crude material (100:1 hexane/EtOAc) afforded 5a as pale yellow oil (43.1mg, 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 51% 2: 3% | With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In para-xylene at 140℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; | 4.3.2 Typical procedure for ruthenium-catalyzed alkylation of o-acylanilines with olefins: ruthenium-catalyzed deamination/alkylation of 2a with 4a General procedure: To a 10mL Schlenk tube were added in a glove box o-acylaniline 2a (41.5mg, 0.2mmol), RuH2(CO)(PPh3)3 (1) (36.7mg, 0.04mmol), olefin 4a (0.045mL, 0.3mmol), and p-xylene (0.3mL), and the mixture was heated for 24h in an oil bath whose temperature adjusted to 140°C. After the reaction, n-eicosane (0.1mmol) was added as an internal standard to the resulting mixture, which was then analyzed by GC. Column chromatography of the crude material (100:1 hexane/EtOAc) afforded 5a as pale yellow oil (43.1mg, 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 71% 2: 1% | With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In para-xylene at 140℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; | 4.3.2 Typical procedure for ruthenium-catalyzed alkylation of o-acylanilines with olefins: ruthenium-catalyzed deamination/alkylation of 2a with 4a General procedure: To a 10mL Schlenk tube were added in a glove box o-acylaniline 2a (41.5mg, 0.2mmol), RuH2(CO)(PPh3)3 (1) (36.7mg, 0.04mmol), olefin 4a (0.045mL, 0.3mmol), and p-xylene (0.3mL), and the mixture was heated for 24h in an oil bath whose temperature adjusted to 140°C. After the reaction, n-eicosane (0.1mmol) was added as an internal standard to the resulting mixture, which was then analyzed by GC. Column chromatography of the crude material (100:1 hexane/EtOAc) afforded 5a as pale yellow oil (43.1mg, 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With carbonylchlorohydridobis(tricyclohexylphosphine)ruthenium(II) In toluene at 120℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With [(1,5-cyclooctadiene)(OH)iridium(I)]2; N-benzoyl-methanesulfonamide; water-d2 In tetrahydrofuran at 70℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With palladium(II) acetylacetonate; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; toluene-4-sulfonic acid at 120℃; for 20h; Schlenk technique; Inert atmosphere; Autoclave; | General procedure: Reaction conditions for ligand 1:In a 25 ml Schlenk container under argon[Pd (acac) 2] (12.2 mg, 0.04 mol),1 (69.8 mg, 0.16 mmol),PTSA (114 mg, 0.6 mmol) and MeOH (25 ml).In a 4 ml glass vial equipped with a magnetic stirrer, 2 mmol of olefin was charged.Add 1.25 ml of the previously prepared mother liquor to the syringe.The vial was placed on a metal plate in a 300 ml Parr autoclave under argon.The autoclave was purged with CO three times and then pressed into 40 bar of CO.Then under magnetic stirring and the reaction carried out at 120 deg.] C 20 h.Then cool and slowly release the pressure.Add 0.2 ml of isooctane as an internal standard.The conversion and yield were determined by GC and GC-MS analysis. |
82% | With platinum(II) bis(acetylacetonate); C28H36P2; toluene-4-sulfonic acid at 120℃; for 20h; Sealed tube; Inert atmosphere; Autoclave; | |
79% | With 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane; palladium(II) acetylacetonate; toluene-4-sulfonic acid for 20h; Sealed tube; Inert atmosphere; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With dichloro bis(acetonitrile) palladium(II); silver(I) acetate In 1,2-dichloro-ethane at 40℃; for 16h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 49% 2: 9% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tris(triphenylphosphine)ruthenium(II) chloride; sodium phosphate In toluene at 160℃; for 18h; Sealed tube; | (I) General procedure for the Ruthenium-catalyzed alkylation of aromatic amides withVinylsilane. General procedure: To an oven-dried 5 mL screw-capped vial, N-(quinolin-8-yl)-1-naphthamide (89.5mg, 0.3 mmol),Triethylvinylsilane (213.5 mg, 1.5 mmol), RuCl2(PPh3)3 (28.8 mg, 0.03 mmol), Na3PO4 (12.3 mg,0.075 mmol) and toluene (0.75 mL) were added. The mixture was stirred for 18 hours at 160° C andthen allowed to cool to room temperature. The resulting mixture was filtered through a pad of celiteand the filtrate then concentrated in vacuo. The residue was purified by column chromatography onsilica gel (eluent: hexane/EtOAc = 20/1 to 10/1) to afford the alkylation product 3aa (102.9 mg,78%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With trans-bis(acetonitrile)palladium(II) chloride; silver(I) acetate In 1,2-dichloro-ethane at 40℃; for 8h; | 2 Example 2 The difference between Example 2 and Example 1 is that a method for preparing an arvinylsilane compound includes the following steps: Adding 0.1165 g of N-methyl-2-naphthyl-1-aniline to a 25 mL reaction tube 0.29 mL of triethylvinylsilane, 0.0130 g of bis(acetonitrile)palladium dichloride, and 0.0835 g of silver acetate, and 5 mL of 1,2-dichloroethane were added. The reaction tube was moved to an oil bath at 40 ° C. for 8 h. After flash column chromatography, the product was concentrated under reduced pressure with a yield of 71%. Otherwise, it is the same as that of Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium hydrogensulfate; pentafluorophenylthiol; fac-tris[2-phenylpyridinato-C2,N]iridium(III); sodium L-ascorbate In water; acetonitrile for 16h; Autoclave; Inert atmosphere; Irradiation; | Typical procedure for the 1,2-hydro(tosylmethylation) of alkene 1a with phosphonium iodide 4 (Scheme1). General procedure: Phosphonium iodide 4 (223 mg, 0.40 mmol), fac-Ir(ppy)3 (1.3 mg, 0.002 mmol, 1.0 mol%), sodiumascorbate (79.4 mg, 0.40 mmol), and KHSO4 (81.4 mg, 0.60 mmol) were added to a vial (Biotage, 2-5 mL)equipped with a stir bar. The vial was flushed with argon gas and quickly capped with a Teflon septum. 4-Phenylbut-1-ene (1a, 26.4 mg, 0.20 mmol), C6F5SH (4.02 mg, 0.02 mmol, 10 mol%), distilled CH3CN (2.5mL), and H2O (2.5 mL; degassed with argon gas for 30 min) were added via syringe. The mixture was stirredvigorously for 16 hours under blue LED lights (470 nm, 23 W) while the vial being cooled with a fan. Then,the mixture was diluted with brine (25 mL) and extracted with CH2Cl2 (25 mL x 3). The organic phase wasdried with Na2SO4. The resulting solution was concentrated under reduced pressure. The residue was purifiedby PTLC (hexane/ethyl acetate= 3:1) to give 3a (49.2 mg, 0.16 mmol, 81% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With tetrakis(trimethylphosphine)iron(0) In neat (no solvent) at 50℃; for 0.0666667h; Glovebox; | Deuterium-Labeling Experiment Using 1-d4 and Alkenes 2; General Procedure General procedure: An oven-dried 10 mL Schlenk tube containing a magnetic stirring bar was charged with Fe(PMe3)4 (0.03-0.06 mmol 5-10 mol%), alkene 2 (0.9 mmol), and 1b-d4 (0.6 mmol) in a glove box and transferred out of the glove box. The resulting mixture was heated at 50 or 70 °C for 4-240 min. The reaction was stopped by exposing the mixture to air. After transferring the remaining alkene 2 to a trap cooled by liquid N2 under reduced pressure, the mixture was passed through a short plug of silica gel using EtOAc as an eluent to remove the remaining iron complexes. All the volatile materials of the eluate were removed by rotary evaporation. The remaining ketone 1b-dn and product 3 were obtained by silica gel flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: pyridine; vinyltriethylsilane With C46H41AlN3P2Rh at 150℃; for 18h; Inert atmosphere; Glovebox; Stage #2: With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 15h; | General Procedure for Table 3 In a glove box, a 4 mL vial containing a stirring bar was charged with complex 6 (25 mg, 30 μmol) or 7 (21 mg, 30 μmol), 1b (47 mg, 0.60 mmol), alkene (2; 1.8 mmol), and n-dodecane (30 μL, 22 mol%) as an internal standard, and the resulting mixture was stirred for 18 h at 150 °C. The regioselectivity was determined by GC analysis of the reaction mixture. The reaction mixture was filtered through a membrane filter with dichloromethane and concentrated in vacuo. Then, the residue was purified by MPLC [Biotage SNAP Ultra or Biotage Sfär Silica HC D] to give the target compound. In all cases, other alkylpyridines were not detected. 2-(2-(Triethylsilyl)ethyl)pyridine (3bb): The reaction of 2b (0.26 g, 1.8 mmol) with 6 gave a mixture of 3bb, 4bb, and 5bb (3bb:4bb:5bb = 91:8:1). The mixture was filtered through a membrane filter with dichloromethane and concentrated in vacuo. Then, a 30 mL recovery flask containing a stirring bar was charged with the residue, palladium 10% on carbon (20 mg) and ethanol (2.0 mL), and the resulting mixture was stirred under H2 (1.0 atm) for 15 h at room temperature. The reaction mixture was filtered through a membrane filter with ethanol and concentrated in vacuo. The residue was again filtered through a membrane filter with n-hexane and all the volatiles were removed in vacuo. It is noted that 4bb and 5bb were not detected in 1H NMR after hydrogenation. The residue was purified by MPLC [BiotageSfär Silica HC D, n-hexane/ethyl acetate/triethylamine (98:2:1 to 90:10:1 to 70:30:1)] to afford 3bb as a yellowish oil (81 mg, 0.37 mmol, 61%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iridium(III) chloride n-hydrate; bis(4-methoxyphenyl)phenylphosphine; toluene-4-sulfonic acid; 1,2-bis<bis(p-trifluoromethylphenyl)phosphino>ethane In 1-methyl-pyrrolidin-2-one; water at 140℃; for 20h; Autoclave; |
Tags: 1112-54-5 synthesis path| 1112-54-5 SDS| 1112-54-5 COA| 1112-54-5 purity| 1112-54-5 application| 1112-54-5 NMR| 1112-54-5 COA| 1112-54-5 structure
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