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CAS No. : | 67191-35-9 | MDL No. : | MFCD20384496 |
Formula : | C11H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SXCKVSZTZAMSRS-UHFFFAOYSA-N |
M.W : | 162.23 | Pubchem ID : | 5461811 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.64 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.83 cm/s |
Log Po/w (iLOGP) : | 2.73 |
Log Po/w (XLOGP3) : | 3.47 |
Log Po/w (WLOGP) : | 3.01 |
Log Po/w (MLOGP) : | 2.96 |
Log Po/w (SILICOS-IT) : | 3.15 |
Consensus Log Po/w : | 3.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.101 mg/ml ; 0.000625 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.35 |
Solubility : | 0.0732 mg/ml ; 0.000451 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.4 |
Solubility : | 0.0652 mg/ml ; 0.000402 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.65 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.66 g | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 4 h; Stage #2: for 1 h; |
Synthesis of 1-isopropoxy-2-vinylbenzene. A suspension of 15.65 g of methyl triphenylphosphonium bromide in 100 mL of dry THE was treated at room temperature with 19.0 mL of n-BuLi (2.5 M solution in n-hexane). The resulting orange solution was stirred for 4 hours. Then, a solution of 6.00 g (36.5mmol) of 2-isopropoxybenzaldehyde in 25 mL of dry THE was added dropwise. Upon addition, a white precipitate formed. The suspension was stirred for 1 hour and concentrated in vacuo to give a viscous yellow oil that was purified by passing through a short column of Si02 (heptane) then vacuum distillation to yield 3.66 g of 1-isopropoxy-2-vinylbenzene as a colorless liquid. 1H-NMR (300 MHz, CDCI3): 51.27 (d, J=6.1 Hz, 6H), 4.47 (m, 1H), 5.15 (dd, Ji=11.2 Hz, J2=1.6 Hz, 1H), 5.65 (dd, Ji=17.8Hz, J2=1.6 Hz, IH), 6.78—6.88 (m, 2H), 6.92—7.05 (m, 1H), 7.08—7.16 (m, IH), 7.40 (dd, J1=7.6 Hz, J2=1.7 Hz, 1H). GC-MS: >99.0percent MS (El): 162. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) chloride; | EXAMPLE 1 Metathesis by Ethenolysis of Methyl Oleate Catalyzed by a Type 3 Complex (FIG. 1) in an Ionic Liquid; 1 ml of 3-butyl-1,2-dimethylimidazolium bis-triflylamide with formula [BMMI]+[N(CF3SO2)2]- pre-dried overnight at 80° C., 148 mg of methyl oleate (source: Fluka, with a purity higher than 98percent) and 15 mg of the complex with formula Cl2Ru(CH-o-O-iPrC6H4)PCy3 (synthesized by reacting the 1st generation Grubbs complex with formula Cl2Ru(CHC6H5)(PCy3)2 with 1-isopropoxy-2-vinylbenzene in the presence of CuCl), this corresponding to 5percent molar of catalyst with respect to methyl oleate, were introduced, in an inert atmosphere of argon, into an autoclave reactor provided with an agitation system and a pressure sensor. The autoclave was then placed under vacuum and pressurized to obtain a pressure of 10 bars (1 MPa) of ethylene (origin: Alphagas, quality N25). The temperature was kept constant at 20° C. The medium was stirred at ambient temperature for 2 hours, then the excess ethylene was slowly purged by returning to atmosphere pressure at a temperature not exceeding 20° C. and the autoclave was again placed under an atmosphere of argon. The products were separated from the ionic liquid by adding 2 to 3 ml of heptane distilled over CaH2 and degassed. An aliquot (100 mul) of the extracted solution was passed through a short silica column (2 cm) eluted with diethyl ether. It was analyzed by gas phase chromatography (ZB-1 column, 100percent dimethylpolysiloxane, 30 metres, helium vector gas 2 ml/min, temperature programming: 60° C. then 5° C./min to 220° C.) coupled to a mass spectrometer. The methyl oleate conversion was 95percent. It was calculated using decane as an internal reference. The reaction products were composed of 1-decene (fraction A) and methyl decenoate (fraction B). The presence of 1-decene isomers was not detected. Homo-metathesis products were present in trace amounts and could not be quantified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) chloride; In dichloromethane; for 0.75h;Schlenk technique; Inert atmosphere; Reflux; | General procedure: The product was synthesized using in-situ generated Grubbs-Hoeyda 2nd generation catalyst.Therefore Grubbs 2nd generation catalyst (0.1 mmol, 0.02 equiv.) was dissolved in drydichloromethane (5 mL), 1-Isopropoxy-2-vinylbenzene (0.1 mmol, 0.02 equiv.) and copper(I)chloride(0.1 mmol, 0.02 equiv.) were added and the reaction mixture was stirred at reflux for 45 min until thecolour turned green. After cooling to room temperature VCP XX (5 mmol, 1 equiv.) and methylacrylate (30 mmol, 6 equiv.) were added and the reaction mixture was stirred at reflux for 16 h, afterwhich additional methyl acrylate (10 mmol, 2 equiv.) was added and stirred for another 7 h at reflux.The product was obtained via column chromatography on silica gel (5:1 petroleum ether/ethylacetate) as a white powder |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | A vacuum dried Schlenk flask was charged with imidazolium hydrochloride salt 4b (129 mg, 0.26 mmol, 1.15 eq.) and 10 mL dry toluene was introduced into the flask using a syringe. The white suspension thus formed was vigorously agitated and to it was introduced under an argon atmosphere solid KHMDS (95 %, 60 mg, 0.28 mmol, 1.23 eq.). The suspension turned homogeneous and was left to stir for 30 min. To this was then introduced, under an argon atmosphere, Grubbs first generation catalyst (190 mg, 0.23 mmol, 1.0 eq.) and the mixture was left stirring for another 2 hours at room temperature. The toluene was then evaporated in vacuuo to give a dark brown coloured semisolid. No purification of this mixture was attempted, however as significant degradation and loss of intermediate complex was observed. The crude brown semisolid was then redissolved in 10 mL of DCM and to this was introduced CuCl (91 mg, 0.92 mmol, 4 eq.) and <strong>[67191-35-9]1-isopropoxy-2-vinylbenzene</strong> (75 mg, 0.46 mmol, 2 eq.) and the mixture stirred at 40C for 3 hours. The reaction was then cooled and DCM evaporated in vacuuo to give a dark green coloured semisolid. The semisolid was first washed with dry, distilled pentane (2×50 mL) and dried under high vacuum. The resulting green powder was loaded onto a column of silica gel soaked in pentane. This was then eluted successively using pure pentane to remove unreacted vinylbenzene and then a 1/1 mixture of pentane/DCM and finally pure DCM to remove a green band which was collected and dried under high vacuum to yield a green coloured amorphous powder. C41H58N2OCl2Ru (766.88) calc. for C 64.21, H 7.62, N 3.65, found C 64.36, H 7.68, N 3.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(l) chloride; In dichloromethane; | A vacuum dried Schlenk flask was charged with complex 15 (330 mg, 0.287 mmol, 1 eq.), CuCl (88 mg, 0.88 mmol, 3.1 eq.) and 96 mg, 0.60 mmol 2.1 eq.) of <strong>[67191-35-9]1-isopropoxy-2-vinylbenzene</strong>. Dry DCM was then added to this reaction and the reaction was stirred at 40C for 3 hours, cooled to room temperature and the DCM evaporated in vacuuo to yield dark green colored powder. The powder was re-dissolved in 5 mL of DCM and silica (50 mg) was added to the solution and it was again evaporated on a rotary evaporator at 30C to give a free flowing powder. It was then loaded onto a column pre-wet with pure pentane. The column was first eluted with a 4/1 mixture of DCM/pentane and then with a 1/1 mixture of DCM/pentane to elute a green band which was collected and evaporated under high vacuum to yield a green crystalline powder, which was recrystallized a 3/1 mixture of diethyl ether/toluene. C51H66N2O3Cl2Ru (927.06) calc. C 66.07,H 7.18, N 3.02 found C 66.07, H 7.07, N 2.99. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(l) chloride; In dichloromethane; at 40℃; for 3h;Inert atmosphere; | A flame dried Schlenk flask was charged with complex 16 (687 mg, 0.649 mmol, 1 eq.), CuCl (250 mg, 2.52 mmol, 3.9 eq.) and <strong>[67191-35-9]1-isopropoxy-2-vinylbenzene</strong> (223 mg, 1.37 mmol 2.1 eq.) of. To this was added dry DCM ( 50 mL) and the reaction was stirred at 40C for 3 hours, cooled to room temperature and the DCM evaporated in vacuuo to yield dirty green colored powder. The powder was re-dissolved in 5 mL of DCM and silica (200 mg) was added to the solution and it was again evaporated on a rotary evaporator at 30C to give a greenish-brown free flowing powder. It was then loaded onto a column pre-wet with pure pentane. The column was first washed with pentane (10 mL) and then eluted with a 1:1 mixture of DCM/EtOAc to elute a green band which was then collected and evaporated in vacuo to give a greencoloured sticky paste. This was then triturated with pentane and dried overnight to give a green coloured powder (433 mg, 80% yield).This powder was then crystallized using a 1/3 mixture of DCM/pentane to obtain green coloured mono-crystals for X- ray diffraction studies. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | A vacuum dried Schlenk flask was charged with imidazolium hydrochloride salt 4a (166 mg, 0.39 mmol, 1.15 eq.) and 10 mL dry toluene was introduced into the flask using a syringe. The white suspension thus formed was vigorously agitated and to it was introduced under an argon atmosphere solid KHMDS (95 %, 88 mg, 0.42 mmol, 1.23 eq.). The suspension turned homogeneous and was left to stir for 30 min. To this was then introduced, under an argon atmosphere, Grubbs first generation catalyst (283 mg, 0.34 mmol, 1.0 eq.) and the mixture was left stirring for another 2 hours at room temperature. The toluene was then evaporated in vacuuo to give a dark brown coloured semisolid. No purification of this mixture was attempted, however as significant degradation and loss of intermediate complex was observed, the crude brown semisolid was then redissolved in 10 mL of DCM and to this was introduced CuCl (134 mg, 0.92 mmol, 4 eq.) and <strong>[67191-35-9]1-isopropoxy-2-vinylbenzene</strong> (110 mg, 0.68 mmol, 2 eq.) and the mixture stirred at 40C for 3 hours. The reaction was then cooled and DCM evaporated in vacuuo to give a dark green coloured semisolid. The semisolid was first washed with dry, distilled pentane (2×50 mL) and dried under high vacuum. The resulting green powder was loaded onto a column of silica gel soaked in pentane. This was then eluted successively using pure pentane to remove unreacted vinylbenzene and then a 1/1 mixture of pentane/DCM and finally pure DCM to remove a green band which was collected and dried under high vacuum to yield a green coloured amorphous powder. C39H54N2OCl2Ru (738.83) calc. C 63.40, H 7.37, N 3.79, found C 63.31, H 7.61, N 3.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With Amberlyst 15-A resin; In tetrahydrofuran; at 40℃; for 1h;Inert atmosphere; | A flame-dried Schlenk reaction ask is charged with a stir bar and put under an Ar atmosphere. 748 mg [Dichloro-(3-phenyl-1H-inden-1-yliden)-(1,3-dimesityl-4,5-dihydro-imidazol-2-ylidene)-(pyridine)-ruthenium(II)] 2c (1.00 mmol, Umicore AG & Co KG, Hanau), 173 mg <strong>[67191-35-9]2-isopropoxystyrene</strong> (1.05 mmol; 1.05 equiv) and 1026 mg Amberlyst 15-A resin (4.00 mmol; 4 equiv) is loaded into the reaction ask and 25 mL THF is added. The reaction mixture is stirred at 40 C. for 1 hour, during which the reaction mixture turns from red to green color. Then, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the polystyrene sulfonic acid resin. Evaporation of all volatiles, suspending in 20 mL n-hexane and subsequent filtration and drying in vacuo afforded 578 mg of the desired compound 3b as a green, air-stable product (yield: 94%). 1H and 13C NMR analytics are in agreement with those found in literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With Amberlyst 15-A resin; In dichloromethane; at 40℃; for 1.25h;Inert atmosphere; | A flame-dried Schlenk reaction flask is charged with a stir bar and put under an Ar atmosphere. 923 mg [Dichloro-(3-phenyl-1H-inden-1-ylidene)-bis-(tricyclohexyl-phosphine)-ruthenium(II)] 2a (1.0 mmol; Umicore AG & Co KG, Hanau), 173 mg <strong>[67191-35-9]2-isopropoxystyrene</strong> (1.05 mmol; 1.05 equiv.; Aldrich) and 1026 mg Amberlyst 15-A resin in dry form (4.0 mmol, 4 equiv.; Rohm and Haas Co., Philadelphia, USA) are loaded into the reaction flask and 25 mL dichloromethane (DCM) is added. The reaction is stirred at 40 C. for 75 minutes and the solution colored from red to brown. Subsequently, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the Amberlyst resin. Evaporation of all volatiles, suspending the residue in 20 mL n-hexane and subsequent filtration and drying of the precipitate in vacuo afforded 548 mg of the desired compound 3a (yield: 91%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With Amberlyst 15-A resin; In tetrahydrofuran; at 68℃; for 1h;Inert atmosphere; | A flame-dried Schlenk reaction flask is charged with a stir bar and put under an Ar atmosphere. 949 mg [Dichloro-(3-phenyl-1H-inden-1-yliden)-(1,3-dimesityl-4,5-dihydro-imidazol-2-ylidene)-(tricyclohexylphosphine)-ruthenium(II)] 2b (1.0 mmol; Umicore AG & Co KG, Hanau), 173 mg <strong>[67191-35-9]2-isopropoxystyrene</strong> (1.05 mmol; 1.05 equiv.) and 1026 mg Amberlyst 15-A resin in dry form (4.0 mmol; 4 equiv) was loaded into the reaction flask and 25 mL THF is added. The reaction is stirred at 68 C. for 1 hour, during which the reaction mixture colors from red to green. Then, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the Amberlyst resin. Evaporation of all volatiles, suspending the residue in 20 mL n-hexane and subsequent filtration and drying of the precipitate in vacuo afforded 576 mg of the desired compound as a green, air-stable product (yield: 94%). The and 13C NMR spectral data of the dried greenish powder were in accordance to literature reports. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Amberlyst 15-A resin; In tetrahydrofuran; at 40℃; for 1.5h;Inert atmosphere; | A flame-dried Schlenk reaction flask is charged with a stir bar and put under an Ar atmosphere. 849 mg 1b (1.00 mmol), 173 mg <strong>[67191-35-9]2-isopropoxystyrene</strong> (1.05 mmol; 1.05 equiv) and 1026 mg Amberlyst 15-A resin in dry form (4.00 mmol; 4 equiv) was loaded into the reaction flask and 25 mL THF is added. The reaction was stirred at 40 C. for 1.5 hour, during which the reaction mixture colors from pink to green. Then, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the polystyrene sulfonic acid resin. Evaporation of all volatiles, suspending in 20 mL hexane and subsequent filtration and drying in vacuo afforded the desired compound 3b as a green air-stable product. 1H and 13C NMR analyses are in agreement with those found in literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | A solution of 3a (0.88 g, 1.5 mmol) in THF (20 mL) was treatedwith tBuOK (1 M THF solution, 1.5 mL, 1.5 mmol) at room temperatureunder an Ar flow. To the mixture, a solution of Grubbs catalyst1st generation (0.83 mg, 1.0 mmol) in benzene (20 mL) wastransferred via cannula. After stirring at 80 C for 30 min underAr atmosphere, all volatiles were removed under vacuum. ThenCuCl (0.21 g, 2.1 mmol), 2-isopropoxystylene (0.17 g, 1.0 mmol)and CH2Cl2 (20 mL) were added to the residue and the resultingsuspension was stirred at 40 C for 1 h. The reaction mixture wasconcentrated to dryness, and the residue was purified by silicagel column chromatography using pentane/CH2Cl2 = 1/1 (v/v) asan eluent. Further purification was performed with preparativerecycling GPC. Recrystallization from CH2Cl2/pentane afforded darkgreen crystals. Yield 0.24 g (29%). Anal. Calc. for C43H46Cl2N2O3Ru:C, 63.70; H, 5.72; N, 3.45. Found: C, 63.88; H, 5.76; N, 3.43%. 1HNMR (400 MHz, CDCl3): d 16.65 (s, 1H, RuCHAr), 7.50-7.34 (m,11H, ArH), 6.93-6.78 (m, 13H, ArH), 5.13 (s, 4H, ArCH2), 4.90 (sept.,J = 6.0 Hz, 1H, CH(CH3)2), 4.14 (s, 4H, N(CH2)2N), 2.48 (s, 12H,ArCH3), 1.29 (d, J = 6.3 Hz, 6H, CH(CH3)2). 13C NMR (100 MHz,CDCl3): d 297.29, 212.27, 158.76, 152.25, 145.28, 136.99, 129.55,128.63, 127.97, 127.29, 122.92, 122.28, 114.58, 112.82, 74.97,69.98, 51.67, 21.11. MALDI-TOF MS (DIT): m/z 811 [M]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | General procedure: A solution of 3a (0.88 g, 1.5 mmol) in THF (20 mL) was treatedwith tBuOK (1 M THF solution, 1.5 mL, 1.5 mmol) at room temperatureunder an Ar flow. To the mixture, a solution of Grubbs catalyst1st generation (0.83 mg, 1.0 mmol) in benzene (20 mL) wastransferred via cannula. After stirring at 80 C for 30 min underAr atmosphere, all volatiles were removed under vacuum. ThenCuCl (0.21 g, 2.1 mmol), 2-isopropoxystylene (0.17 g, 1.0 mmol)and CH2Cl2 (20 mL) were added to the residue and the resultingsuspension was stirred at 40 C for 1 h. The reaction mixture wasconcentrated to dryness, and the residue was purified by silicagel column chromatography using pentane/CH2Cl2 = 1/1 (v/v) asan eluent. Further purification was performed with preparativerecycling GPC. Recrystallization from CH2Cl2/pentane afforded darkgreen crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | General procedure: A solution of 3a (0.88 g, 1.5 mmol) in THF (20 mL) was treatedwith tBuOK (1 M THF solution, 1.5 mL, 1.5 mmol) at room temperatureunder an Ar flow. To the mixture, a solution of Grubbs catalyst1st generation (0.83 mg, 1.0 mmol) in benzene (20 mL) wastransferred via cannula. After stirring at 80 C for 30 min underAr atmosphere, all volatiles were removed under vacuum. ThenCuCl (0.21 g, 2.1 mmol), 2-isopropoxystylene (0.17 g, 1.0 mmol)and CH2Cl2 (20 mL) were added to the residue and the resultingsuspension was stirred at 40 C for 1 h. The reaction mixture wasconcentrated to dryness, and the residue was purified by silicagel column chromatography using pentane/CH2Cl2 = 1/1 (v/v) asan eluent. Further purification was performed with preparativerecycling GPC. Recrystallization from CH2Cl2/pentane afforded darkgreen crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With copper(l) chloride; In dichloromethane; at 35℃; | The ruthenium complex of formula 1.2 (0.309 g; 0.344 mmol; 1 eq.) (also called [(5-cyclopentyl-2-mesityl)-imidazo-1-lidene]dichloro(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphospine)ruthenium) was reacted with the styrenyl ether of formula 2H (65 mg; 0.37 mmol; 1.1 eq.). The reaction is carried out in the presence of dichloromethane (DCM; 3.5 mL) and copper(l) chloride (CuCl; 36.8 mg; 0.37 mmol; 1.1 eq.), at 35 C. for 5 hours.After purification on a silica gel column, the alkylidene ruthenium complex of formula 1.5 is obtained (89 mg; 0.158 mmol; 45%):in which Mes represents the mesityl group.The reaction scheme is shown below:In this reaction scheme, Cy3P represents tricyclohexylphosphine, Mes represents the mesityl group, and Ph represents a phenyl group.The scheme shows that the product obtained, at a yield of 45%, is the alkylidene ruthenium complex of formula 1.5.NMR1H (400 MHz, CDCl3): 16.42 (s, 1H); 7.50 (m, 1H); 7.27 (m, 1H); 7.10 (s, 2H); 7.01 (m, 1H); 6.95 (m, 2H); 6.88 (d, J=2 Hz, 1H); 5.96, (q, J=7.5 Hz, 1H); 5.18 (sept., J=6.21 Hz, 1H);13C (100 MHz, CDCl3): 172.2; 152.7; 144.5; 139.6; 137.6; 137.4; 129.3; 129.0; 125.0; 122.7; 122.4; 118.5; 113.0; 75.1; 64.2; 34.4; 24.7; 22.0; 21.4; 18.2.The alkylidene ruthenium complex of formula 1.5 was isolated and was submitted to various studies. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(l) chloride; In dichloromethane; at 35℃; | D.1. Synthesis of an Alkylidene Ruthenium Complex of the Chelating Type from the Ruthenium Complex of Formula 1.1 and a Styrenyl Ether of Formula 2H The ruthenium complex of formula 1.1 (0.297 g; 0.300 mmol; 1 eq.) (also called [(5-cyclododecyl-2-mesityl)-imidazo-1-lidene]dichloro(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium) was reacted with the styrenyl ether of formula 2H, namely <strong>[67191-35-9]isopropoxyphenyl-2-propenyl</strong>. The reaction is carried out in the presence of dichloromethane (DCM; 3 mL) and copper(I) chloride (CuCl; 35.2 mg; 0.35 mmol; 1.2 eq.), at 35 C. for 5 to 6 hours. After purification on a silica gel column, the desired complex of formula 1.3 was isolated at a yield of 60% (120 mg; 0.178 mmol). In this way the alkylidene ruthenium complex of formula 1.3 is obtained: in which Mes represents the mesityl group. The number 12 in formula 1.3 indicates that each cycloalkyl group is a cyclododecyl group.10259] The reaction scheme is shown below:10260] In this reaction scheme, PCy3 represents tricyclohexylphosphine and Mes represents the mesityl group.10261] The scheme shows that the product obtained, at ayield of 60%, is the alkylidene ruthenium complex of formula1.3.j0262] The alkylidene ruthenium complex of formula 1.3 was isolated.10263] NMR:j0264] ?H(400MHz,CDC13): 16.47(s, 1H);7.51 (m, 1H);7.28 (d, J=2 Hz); 7.10 (s, 2H); 7.00 (m, 1H); 6.93 (m, 2H);6.85 (d, J=2 Hz); 5.67 (sept., J=5.8 HZ, 1H); 5.17 (sept., J=7Hz, 1H); 2.50 (s, 3H); 2.23 (m, 4H); 2.02 (s, 6H); 1.80 (d,J=5.8 Hz, 6H); 1.75-1.45 (m, 14H)j0265] ?3C(100MHz,CDC13): 171.3; 152.3; 144.8; 139.6; 137.7; 137.6; 129.3; 129.0; 124.4; 122.7; 122.4; 120.1; 113.1;61.1; 30.6; 25.7; 23.2; 23.1; 22.2; 21.6; 18.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45 mg | Example 5: Synthesis of Compound 16. A solution of TBS-Bitet-2-OH (86 mg) in 2 mL benzene was added dropwise to a solution of W(N-2,6-C12C6H3)(CHCMe3)-(NC4(CH3)2H2)2 (100 mg) in benzerie (2 mL). The reaction mixture was stirred at room temperature for 4 hours and the volatile materials were removed under vacuum. The residue was dissolved in DME (2 mL) and a solution of 1-(isopropoxy)-2- vinylbenzene (49 mg) in DME (2mL) was added in one portion and continued the stirring for further 4hours. After that the reaction mixture was concentrated in vacuo to provide a deep-red oil from which the expected product was crystallized by n-pentane (45 mg). 1H-NMR (200 MHz, C6D6): 6 -0.10 (5, 3H), 0.01 (s, 9H), 038 (s, 3H), 0.85 (s, 6H), 1.00-1.60 (m, 16H), 1.90-2.60 (m, 6H), 4.93 (m, 1H),6.04-6.24 (m, 3H), 6.44-6.65 (m, 2H), 6.70-6.81 (m, 3H), 6.95 (1, J=7.3 Hz, IH), 7.22-7.26 (m, 2H), 11.44(s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(l) chloride; In dichloromethane; at 20℃; for 1h;Inert atmosphere; | General procedure: A 50 mL two-necked flask was replaced with argon followed by the addition of ligand 8 (10 mmol, 8a, 8b, 8c, 8d, 8e, 8f, 8g, or 8h), CuCl (30mmol, 3eq) and 25mL of dry dichloromethane (DCM). ), after replacing it three times with argon gas, the closed system was protected with an argon balloon. The ruthenium complex 4a (10 mmol) was added under argon atmosphere, and reacted at room temperature for 1.0 hour. Until the raw material 4a. After the reaction was completed, the silica gel was added to the filtrate, and the crude product was obtained by silica gel column chromatography, and then purified by washing with methanol or pentane-DCM to obtain a green solid product 9 (10 mmol, 9a, 9b, 9c, 9d, 9e, 9f, 9g, or 9h). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.3% | Under anhydrous and anaerobic conditions,Grubbs first generation catalyst 1a (1.22mmol)Add to a 100mL Schlenk bottle,Compound IIIaa (2858 mg, 2.43 mmol) andPotassium tert-butoxide (286 mg, 2.55 mmol)Add to the reaction bottle,Add 50 mL of n-hexane.After reacting at 60 C for 5 hours with stirring,TLC monitored the reaction completely.After the reaction was completed, n-hexane was removed under reduced pressure.The intermediate obtained in the previous step was dissolved in 40 mL of dichloromethane.Add cuprous chloride (300 mg, 1.42 mmol) and stir for 5 min.Compound 2a1 (296 mg, 1.82 mmol) was added to the reaction flask and the temperature was raised to 40 C.TLC monitored the reaction completely.After completion of the reaction, column chromatography gave 574 mg of light green solid powder IIaa1, yield: 32.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | Under anhydrous and anaerobic conditions,Grubbs first generation catalyst 1a (1.22mmol)Add to a 100mL Schlenk bottle,Compound IIIba (2863 mg, 2.43 mmol) andPotassium tert-butoxide (477 mg, 4.25 mmol)It was added to the reaction flask, and 50 mL of n-hexane was added.After reacting for 5 hours at 60 C with stirring, the reaction was monitored by TLC.After the reaction was completed, n-hexane was removed under reduced pressure.The intermediate obtained in the previous step was dissolved in 40 mL of dichloromethane.Add cuprous chloride (300 mg, 1.42 mmol) and stir for 5 min.Compound 2a1 (296 mg, 1.82 mmol)It was added to the reaction flask, and the temperature was raised to 40 C, and the reaction was monitored by TLC.After completion of the reaction, column chromatography gave 568 mg of pale green solid powder IIba1, yield: 32.0%. |
Tags: 67191-35-9 synthesis path| 67191-35-9 SDS| 67191-35-9 COA| 67191-35-9 purity| 67191-35-9 application| 67191-35-9 NMR| 67191-35-9 COA| 67191-35-9 structure
[ 120-11-6 ]
1-(Benzyloxy)-2-methoxy-4-(prop-1-en-1-yl)benzene
Similarity: 0.85
[ 4180-23-8 ]
(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene
Similarity: 0.79
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