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CAS No. : | 2044-08-8 | MDL No. : | MFCD09878413 |
Formula : | C6H9Br | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QBUMXSSCYUMVAW-UHFFFAOYSA-N |
M.W : | 161.04 | Pubchem ID : | 519775 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.24 |
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) : | -5.37 cm/s |
Log Po/w (iLOGP) : | 2.25 |
Log Po/w (XLOGP3) : | 2.69 |
Log Po/w (WLOGP) : | 2.84 |
Log Po/w (MLOGP) : | 2.59 |
Log Po/w (SILICOS-IT) : | 2.74 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.53 |
Solubility : | 0.472 mg/ml ; 0.00293 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.34 |
Solubility : | 0.732 mg/ml ; 0.00454 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.14 |
Solubility : | 1.17 mg/ml ; 0.00726 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.16 |
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 |
---|---|---|
81% | With iodine; magnesium In tetrahydrofuran at 40 - 55℃; Inert atmosphere | Under the protection of nitrogen, adding magnesium metal in the reaction bottle 8.0g (0.33mol) and several grain of iodines, prior to dropping funnel in the uniformly mixed methoxy boronic acid frequency that alcohol ester 56.9g (0.36mol), cyclohexene-1-polybromide 48.3g (0.3mol) and anhydrous tetrahydrofuran 300 ml, the temperature rising to outside bath 40-45 degrees, to a first 25 ml mixed solution, after color treats the iodine triggered evanishment standard, the oven-keeping 40-55 degrees between the completion of the dropping of the remaining mixed solution, then subsequently gradually heated up to reflow to continue reaction 2-3 hours, disappearance of the raw material after detection GC, to the reaction liquid 0-10 degree, slowly adding saturated NH4Cl quenching, adjusting for PH 5-6, separating the organic layer, the water layer using MTBE 150 ml extraction a, combined with the organic layer, the saturated salt water washing, solvent evaporation to dryness of the organic layer is concentrated under reduced pressure, then replace the high vacuum pump, collecting 80-83 °C fraction, get colorless transparent liquid 50.5g, yield 81percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydroxide; water; hydrogen at 45℃; for 4.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentabromide; In sulfolane; at 30 - 80℃; for 6h;Inert atmosphere; | Under a nitrogen atmosphere, cyclohexanone (9.8 g, 0.1 mol) and 49.3 g of sulfolane were added to a 250 mL three-necked reaction flask equipped with a condenser and a constant-pressure low-liquid funnel. Nitrogen was replaced three times, and the temperature was raised to 30-40 C with stirring, and phosphorus pentabromide (43.1 g, 0.1 mol) was added in portions.After the addition was completed, the mixture was heated at 80 C and stirred for 6.0 hours. The sample sent by GC to detect the residual of raw materials is less than 0.5%,The product contains alkenyl bromide and fluorene dibromide, and the ratio of the two products is 83%: 17%. The reaction was complete. Negative pressure distillation. The concentrated solution (GC of the two products: 97.6%) was directly used for the next reaction without purification.Place the reaction flask containing the concentrate in the previous step.DBU (22.8 g, 0.15 mol), NaNH2 (7.8 g, 0.2 mol) and 49.3 g of sulfolane were charged. After feeding, heat to 120 C and stir for 5.0 hours.Send samples to detect intermediate residues less than 0.5%,The reaction system was cooled, filtered, and the filtrate was added with liquid paraffin, followed by distillation under reduced pressure to obtain a crude product containing sulfolane, then 12.0 g of liquid paraffin was added, and distillation was continued to obtain 13.2 g of 1-bromocyclohexene, a colorless oily liquid, GC : 98.3%, the molar yield in two steps is 81.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | Under nitrogen protection, 20 g (0.12 mol) of <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> and 34.7 g (0.14 mol) of pinacol borate were added to the three-necked flask.2.0 g (6 mol%) of triphenylphosphine,2.6 g (3 mol%) of trans-bis(triphenylphosphine)palladium(II) dichloride,Potassium phenolate 24.6 g (0.19 mol) and anhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Purified by silica gel column or distillation21.9 g (yield: 85%) cyclohexene-1-boronic acid pinacol ester. |
85% | With trans-bis(triphenylphosphine)palladium dichloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | Add 20 g (0.12 mol) of <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> to a three-necked flask under nitrogen atmosphere.34.7 g (0.14 mol) of bis(pinacolato)diboron and 2.0 g (6 mol%) of triphenylphosphine,2.6 g (3 mol%) of trans-bis(triphenylphosphine)palladium(II) dichloride, 24.6 g of potassium phenolate (0.19 mol) and 250 mL of anhydrous toluene.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours, then the system was cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture is filtered and concentrated under reduced pressure, and purified by silica gel chromatography or by distillation.21.9 g (yield: 85% cyclohexene-1-boronic acid pinacol ester). |
85% | With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | Add 20 g (0.12 mol) of <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> to a three-necked flask under nitrogen atmosphere.34.7 g (0.14 mol), 2.0 g (6 mol%) of triphenylphosphine,Trans-bis(triphenylphosphine)palladium dichloride (II)2.6 g (3 mol%), potassium phenate 24.6 g (0.19 mol) andAnhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Purified by silica gel column or distillation21.9 g (yield: 85%) cyclohexene-1-boronic acid pinacol ester |
85% | With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | Under nitrogen protection, 20 g (0.12 mol) of <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> and 34.7 g (0.14 mol) of pinacol borate were added to the three-necked flask.2.0 g (6 mol%) of triphenylphosphine,2.6 g (3 mol%) of trans-bis(triphenylphosphine)palladium(II) dichloride,Potassium phenolate 24.6 g (0.19 mol) and anhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.It can be purified by silica gel column or distillation to obtain 21.9 g (yield: 85%)Cyclohexene-1-boronic acid pinacol ester. |
85% | With trans-bis(triphenylphosphine)palladium dichloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | Add 20 g (0.12 mol) of <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> to a three-necked flask under nitrogen atmosphere.34.7 g (0.14 mol) of pinacol borate and 2.0 g (6 mol%) of triphenylphosphine,2.6 g (3 mol%) of trans-bis(triphenylphosphine)palladium(II) dichloride,Potassium phenolate 24.6 g (0.19 mol) and anhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure.Purification by silica gel column or distillation gave 21.9 g (yield: 85%) of cyclohexene-1-boronic acid pinacol. |
85% | With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | Under nitrogen protection, 20 g (0.12 mol) of <strong>[2044-08-8]1-bromo-1-cyclohexene</strong>, 34.7 g (0.14 mol) ofpinacol borate and2.0 g (6 mol%) of triphenylphosphine wereadded to the three-necked flask. 2.6 g(3 mol%) of p-di(triphenylphosphine)palladium(II) chloride, 24.6 g (0.19 mol) of potassium phenate and 250 mL of anhydrous toluene.After nitrogen substitution, the reaction was stirred at 50 C for 5hours, then the system was cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.Theorganic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure, and purified by silica gel chromatography or distillationto give 21.9 g (yield: 85%) of cyclohexene-1-boronic acid pinacol ester. |
85% | With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> (20 g, 124.2 mol), boronic acid pinacol ester (34.7 g, 136.6 mol) was added to a three-necked flask under nitrogen atmosphere.Triphenylphosphine (6 mol%), trans-bis(triphenylphosphine)palladium(II) chloride (3 mol%), potassium phenate (24.6 g, 186.3 mol)And anhydrous toluene (250 mL).After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Can be carried out by silica gel column or distillationPurification afforded cyclohexene-1-boronic acid pinacol ester (21.9 g, yield: 85%) |
85% | With trans-bis(triphenylphosphine)palladium dichloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> (20 g, 124.2 mol), pinacol borate (34.7 g, 136.6 mol), triphenylphosphine (6 mol%), was added to a three-necked flask under nitrogen atmosphere.Trans - bis (triphenylphosphine) palladium (II) dichloride (3mol%), potassium phenolate (24.6g, 186.3mol) and anhydrous toluene (250mL). After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water. The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure.Purification by silica gel column or distillation gave cyclohexene-1-boronic acid pinacol ester (21.9 g, yield: 85%). |
85% | With trans-bis(triphenylphosphine)palladium dichloride; potassium phenolate; triphenylphosphine; In toluene; at 50℃; for 5h;Inert atmosphere; | <strong>[2044-08-8]1-bromo-1-cyclohexene</strong> (20 g, 124.2 mol) was added to a three-necked flask under nitrogen atmosphere.Bornazolium diborate (34.7 g, 136.6 mol),Triphenylphosphine (6 mol%), trans-bis(triphenylphosphine)palladium(II) chloride (3 mol%), potassium phenate (24.6 g, 186.3 mol) and anhydrous toluene (250 mL).After nitrogen substitution, the reaction was stirred at 50 C for 5 hours, then the system was cooled to room temperature and quenched with water. The reaction mixture was extracted with a benzene solvent and brine. The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure.Purification by silica gel column or distillation to obtain cyclohexene-1-boronic acid pinacol ester (21.9 g,Yield: 85%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.2 g | Under a nitrogen atmosphere, cyclohexanone (9.8 g, 0.1 mol) and 49.3 g of sulfolane were added to a 250 mL three-necked reaction flask equipped with a condenser and a constant-pressure low-liquid funnel. Nitrogen was replaced three times, and the temperature was raised to 30-40 C with stirring, and phosphorus pentabromide (43.1 g, 0.1 mol) was added in portions.After the addition was completed, the mixture was heated at 80 C and stirred for 6.0 hours. The sample sent by GC to detect the residual of raw materials is less than 0.5%,The product contains alkenyl bromide and fluorene dibromide, and the ratio of the two products is 83%: 17%. The reaction was complete. Negative pressure distillation. The concentrated solution (GC of the two products: 97.6%) was directly used for the next reaction without purification.Place the reaction flask containing the concentrate in the previous step.DBU (22.8 g, 0.15 mol), NaNH2 (7.8 g, 0.2 mol) and 49.3 g of sulfolane were charged. After feeding, heat to 120 C and stir for 5.0 hours.Send samples to detect intermediate residues less than 0.5%,The reaction system was cooled, filtered, and the filtrate was added with liquid paraffin, followed by distillation under reduced pressure to obtain a crude product containing sulfolane, then 12.0 g of liquid paraffin was added, and distillation was continued to obtain 13.2 g of 1-bromocyclohexene, a colorless oily liquid, GC : 98.3%, the molar yield in two steps is 81.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | To a solution of <strong>[2044-08-8]1-<strong>[2044-08-8]bromocyclohexene</strong></strong>6 (161 mg, 1.00 mmol) in Et2O (3 mL) at 78 C was addedtBuLi (6.0 mL, 1.46 M in pentane, 2.19 mmol). The resulting solution was stirred at 78 C for 0.5 h andRT for 20 min. After cooling to 78 C, MgBr2 solution (1.0 mL, 1.0 M in Et2O/benzene = 3:1, 1.00mmol) was added dropwise. The reaction mixture was stirred at 78 C for 10 min and a solution ofaldehyde 4a (150 mg, 0.48 mmol) in Et2O (4 mL) was added dropwise over 5 min. After stirring at78 C for 2 h, the reaction was quenched with sat. aq. NH4Cl (20 mL), and extracted with AcOEt (3 x20 mL). The organic layers were combined, washed with brine (20 mL), dried over MgSO4, andconcentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexane/AcOEt =10:1) to afford 20g (161 mg, 85% yield) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.2% | In ethanol; at 20℃; for 21h; | Example 3; Preparation of Hexafluorophosphate of Compound No. 14; In a reaction flask were put 0.050 mol of 1,2,3-trimethylindole, 0.058 mol of 2-<strong>[2044-08-8]bromocyclohexene</strong>, and 16.0 g of ethanol and caused to react at room temperature for 21 hours. The reaction mixture was concentrated, and 30 ml of acetone was slowly added to the residue. The crystals thus precipitated were collected by filtration and dried in vacuo at 80 C. for 2.5 hours to afford an intermediate, 1,2,3-trimethyl-3-cyclohexenylindolenium bromide, as white crystals in a yield of 47.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.25 g (52%) | With potassium cyanide; In water; ethyl acetate; | EXAMPLE 4 1,1-Dimethylethyl 4-[2-cyclohexen-1-yl-(4-phenoxyphenyl)amino]-1-piperidinecarboxylate STR140 Add a mixture of amine 12 (3.0 g, 8.2 mmol), prepared from 4-phenoxyaniline and N-carboethoxy-4-piperidinone using the procedures of Example, step 1, and <strong>[2044-08-8]cyclohexenyl bromide</strong> (875 mg, 5.4 mmol) in EtOAc (30 ml) to a well stirred suspension of copper (II) perchlorate hexahydrate (1.0 g, 2.7 mmol) and copper metal (207 mg, 3.3 mmol) in EtOAc (15 ml) under N2. After stirring at room temperature for 12 hours, add an aqueous solution of KCN (5.5 g in 70 ml of water). Extract the resultant clear solution with EtOAc (2*100 ml). Dry the combined organic extracts with Na2 SO4 and remove the solvent by distillation. Chromatograph the residue on silica gel using EtOAc/hexane (110)(110) as the eluent to give 1.25 g (52%) of the product 13 as semi-solid foam. Use a similar procedure to prepare compound 4A: |
1.25 g (52%) | With potassium cyanide; In water; ethyl acetate; | Example 4 1,1-Dimethylethyl 4-[2-cyclohexen-1-yl-(4-phenoxyphenyl)amino]-1-piperidinecarboxylate Add a mixture of amine 12 (3.0g, 8.2 mmol), prepared from 4-phenoxyaniline and N-carboethoxy-4-piperidinone using the procedures of Example, step 1, and <strong>[2044-08-8]cyclohexenyl bromide</strong> (875 mg, 5.4 mmol) in EtOAc (30 ml) to a well stirred suspension of copper (II) perchlorate hexahydrate (1.0g, 2.7 mmol) and copper metal (207 mg, 3.3 mmol) in EtOAc (15 ml) under N2. After stirring at room temperature for 12 hours, add an aqueous solution of KCN (5.5 g in 70 ml of water). Extract the resultant clear solution with EtOAc (2 x 100 ml). Dry the combined organic extracts with Na2SO4 and remove the solvent by distillation. Chromatograph the residue on silica gel using EtOAc/hexane (110)(110) as the eluent to give 1.25 g (52%) of the product 13 as semi-solid foam. Use a similar procedure to prepare compound 4A: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
a) 6-Amino-4-(cyclohexyloxy)-2-methylnicotinonitrile To a mixture of sodium 6-amino-3-cyano-2-methylpyridin-4-olate (300 mg, 1.75 mmol) and K2CO3 (485 mg, 3.51 mmol) in DMF (6 ml) was added Cyclohexenylbromide (0.213 ml, 1.84 mmol) and the reaction mixture was stirred at it for 14 h. NaHCO3 (100 ml) was added and the mixture was extracted with EA (5*30 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The resulting product was dissolved in n-PrOH (10 ml), and hydrogenated (1 atm H2, rt) for 1 h over Pd/C (93 mg, 0.088 mmol). The reaction mixture was filtered and the filtrate was adsorbed on celite. Purification by column chromatography (CombiFlash Companion, 10 g SiO2, DCM to DCM:MeOH 9:1) afforded the desired product. LCMS RtM=1.63 min, [M+H]+=232.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Step 1: rac-4-[ieri-Butyl(dimethyl)silyl]oxy}-l-(cyclohex-l-en-l-yI)-l-(5- [(triisopropylsilyl)oxy]methyl}-3-thienyl)butan-l-ol. [00557] To a solution of 1-bromo- l-cyclohexene (880 uL, 7.85 mmol) in THF ( 15 mL) was added 1.70 M of ferf-BuLi in pentane (9.24 mL, 15.7 mmol) at -78 C, and the reaction was stirred for 1 hour at same temperature. To a separate flask, 4-{ [ier?-butyl(dimethyl)silyl]oxy }-l-(5- { [(triisopropylsilyl)oxy]methyl }-3-thienyl)butan-l-one (Int-xxx) (616 mg, 1.31 mmol) was added followed by 0.6 M of lanthanum(III) chloride bis(lithium chloride) complex in THF ( 1.09 raL, 0.65 mmol) and the reaction mixture was stirred for 1 hour. The resulting lithiated cyclohexene solution was added to the ketone at 0 C. After stirring for 30 min at rt, the reaction was quenched by adding saturated aqueous NH4C1 and extracted with EtOAc. The combined organic layers were dried over Na2S04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 10% EtOAc in hexane) to give 662 mg (91 %) of the title compound as colorless oil. NMR (400 MHz, Chloroform-i ) delta 7.00 (s, 1 H), 6.78 (s, 1H), 5.90 - 5.84 (m, 1H), 4.84 (s, 2H), 3.59 (t, / = 5.9 Hz, 2H), 2.80 (s, 1H), 2.07 - 1.98 (m, 4H), 1.99 - 1.88 (m, 2H), 1 .87 - 1.79 (m, 2H), 1.55 - 1.44 (m, 4H), 1.17 - 0.93 (m, 21 H), 0.84 (s, 9H), 0.05 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With iodine; magnesium; In tetrahydrofuran; at 40 - 55℃;Inert atmosphere; | Under the protection of nitrogen, adding magnesium metal in the reaction bottle 8.0g (0.33mol) and several grain of iodines, prior to dropping funnel in the uniformly mixed methoxy boronic acid frequency that alcohol ester 56.9g (0.36mol), cyclohexene-1-polybromide 48.3g (0.3mol) and anhydrous tetrahydrofuran 300 ml, the temperature rising to outside bath 40-45 degrees, to a first 25 ml mixed solution, after color treats the iodine triggered evanishment standard, the oven-keeping 40-55 degrees between the completion of the dropping of the remaining mixed solution, then subsequently gradually heated up to reflow to continue reaction 2-3 hours, disappearance of the raw material after detection GC, to the reaction liquid 0-10 degree, slowly adding saturated NH4Cl quenching, adjusting for PH 5-6, separating the organic layer, the water layer using MTBE 150 ml extraction a, combined with the organic layer, the saturated salt water washing, solvent evaporation to dryness of the organic layer is concentrated under reduced pressure, then replace the high vacuum pump, collecting 80-83 °C fraction, get colorless transparent liquid 50.5g, yield 81percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In the is provided with a dropping funnel, reflux condenser and distilling device for adding the above-mentioned reaction bottle cyclohexene-1-carboxylic acid the dichloromethane solution, hours under room temperature 3-4 add bromine approves the drop 76.8g (0.48mol), each to be the last dropped after the bromine color disappeared, then adding. After finishing joining, first reaction stirring the mixture at room temperature for 30 minutes, TLC (indenyl Triones color) after the raw material is not detected, then adding 1-3% of cyclohexene-1-carboxylic acid, to reduced pressure distillation after does not flow the fluid, adding 50 ml sulfolane dissolved, the temperature is increased to 45-50 degrees, started dropwise 61g DMAP (1mol) sulfolane solution, from air bubbles in the course of dropping, according to the bubble speed controls the dropping of the speed of the DBU, after dripping, the air bubble is not longer escape to, heating to 80-90 degrees reaction 2-4 hours, distilling under reduced pressure to obtain yellowish liquid cyclohexene-1-polybromide 53g, two-step yield 66%. If to be colorless products, need to be once again rectification and purification, recovery rate 95%, of the reaction of the next color is not affected |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 80 °C / Inert atmosphere; Sealed tube 2: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 80℃; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 80 °C / Inert atmosphere; Sealed tube 2: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 80℃; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With pyridine; phosphorus tribromide; In tetrahydrofuran; at -10 - -5℃; for 10h;Large scale; | (Preparation of Raw Material Reagent)To reduce the amount of water in tetrahydrofuran (THF) to be used, dehydration purification was carried out with CaH 2, and a PBr 3 / THF solution (5.0 N) was prepared from commercially available tribromophosphine and this THF solution. A mixed THF solution (5.0 N / 6.0 N) was prepared from commercially available cyclohexanol and commercially available pyridine.(Continuous reaction)First, the entire system inside the apparatus was vacuum dried, and then the reaction was carried out under a high purity argon atmosphere. Next, each of the prepared tribromophosphine solution and cyclohexanol / pyridine mixed solution was filled in a pressure vessel, and the solution was sent to a static stirrer using two triple plunger pumps. The flow rate of the raw material solution was measured with a Coriolis flowmeter, the solution before reaction was cooled with a spiral tube for cooling, then sent to a static stirrer, mixed and subjected to continuous reaction. Temperature control of the raw material was carried out using a temperature sensor equipped on the upstream side of the static stirrer and between the connected static stirrers. The flow rate of both raw material solutions was adjusted to 0.6 L / min to 0.8 L / min. Regarding the raw material temperature, both solutions were controlled from -10 C. to -5 C., and the continuous reaction was carried out for 10 hours.(Postprocessing)Excess solvent was removed by continuously feeding the resultant reaction solution to a distillation vessel in the apparatus and atmospheric distillation of a THF solution. By distilling the reaction solution at around 167 C., 35.9 kg of bromocyclohexene was obtained. The yield was 72%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; 2-(2-dimethylaminovinyl)-1H-inden-1-ol; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 10h; | General procedure: A mixture of phenylamine 1a (0.5 mmol, 46.5 mg), (1-chloro-vinyl)-benzene 2a (0.6 mmol, 83.4 mg), CuI (10 mol %, 9.5 mg), L1 (10 mol %, 20.1 mg) and Cs2CO3 (2 equiv., 325.8 mg) in DMSO (4 mL) was stirred in CO2 at 100 C for 10 h. After completion of the reaction, the mixture was quenched with saturated salt water (10 mL); the solution was extracted with ethyl acetate (3 × 10 mL). The organic layers were combined and dried over sodium sulfate. The pure product was obtained by flash column chromatography on silica gel to afford 3a 96.8 mg in 81% yield. The spectroscopic data of all of the products are represented below. Yellowish oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper(l) iodide; 2-(2-dimethylaminovinyl)-1H-inden-1-ol; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 10h; | General procedure: A mixture of phenylamine 1a (0.5 mmol, 46.5 mg), (1-chloro-vinyl)-benzene 2a (0.6 mmol, 83.4 mg), CuI (10 mol %, 9.5 mg), L1 (10 mol %, 20.1 mg) and Cs2CO3 (2 equiv., 325.8 mg) in DMSO (4 mL) was stirred in CO2 at 100 C for 10 h. After completion of the reaction, the mixture was quenched with saturated salt water (10 mL); the solution was extracted with ethyl acetate (3 × 10 mL). The organic layers were combined and dried over sodium sulfate. The pure product was obtained by flash column chromatography on silica gel to afford 3a 96.8 mg in 81% yield. The spectroscopic data of all of the products are represented below. Yellowish oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(l) iodide; 2-(2-dimethylaminovinyl)-1H-inden-1-ol; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 10h; | General procedure: A mixture of phenylamine 1a (0.5 mmol, 46.5 mg), (1-chloro-vinyl)-benzene 2a (0.6 mmol, 83.4 mg), CuI (10 mol %, 9.5 mg), L1 (10 mol %, 20.1 mg) and Cs2CO3 (2 equiv., 325.8 mg) in DMSO (4 mL) was stirred in CO2 at 100 C for 10 h. After completion of the reaction, the mixture was quenched with saturated salt water (10 mL); the solution was extracted with ethyl acetate (3 × 10 mL). The organic layers were combined and dried over sodium sulfate. The pure product was obtained by flash column chromatography on silica gel to afford 3a 96.8 mg in 81% yield. The spectroscopic data of all of the products are represented below. Yellowish oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper(l) iodide; caesium carbonate; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 20h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper(l) iodide; caesium carbonate; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 20h; Inert atmosphere; Schlenk technique; |
Tags: 2044-08-8 synthesis path| 2044-08-8 SDS| 2044-08-8 COA| 2044-08-8 purity| 2044-08-8 application| 2044-08-8 NMR| 2044-08-8 COA| 2044-08-8 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
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P243 | Take precautionary measures against static discharge. |
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P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
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P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
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P352 | Wash with plenty of soap and water. |
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P362 | Take off contaminated clothing and wash before reuse. |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
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P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
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P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
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Disposal | |
Code | Phrase |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
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 |
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