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CAS No. : | 82832-73-3 | MDL No. : | MFCD04038797 |
Formula : | C15H26O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AKCZQKBKWXBJOF-UHFFFAOYSA-N |
M.W : | 222.37 | Pubchem ID : | 4354185 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.93 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 70.19 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.3 cm/s |
Log Po/w (iLOGP) : | 3.18 |
Log Po/w (XLOGP3) : | 4.73 |
Log Po/w (WLOGP) : | 4.35 |
Log Po/w (MLOGP) : | 3.67 |
Log Po/w (SILICOS-IT) : | 4.2 |
Consensus Log Po/w : | 4.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.0 |
Solubility : | 0.0222 mg/ml ; 0.0000999 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.82 |
Solubility : | 0.00338 mg/ml ; 0.0000152 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.62 |
Solubility : | 0.054 mg/ml ; 0.000243 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trans-4,4'-diaminostilbene-2,2'-disulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; | EXAMPLE 10 4-(trans-4-Propylcyclohexyl)-1-trifluoromethylcyclohex-1-ene A mixture of 10 mmol of <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)cyclohexanone</strong>, 11 mmol of trimethyl(trifluoromethyl)silane, 10 mmol of tetrabutylammonium fluoride and 50 ml of THF is stirred for 2 hours at 0 C. After customary work-up, the crude product is dissolved in 20 mml of THF, 10 mmol of DAST are added, and the mixture is heated to boiling. After customary work-up, the crude product is purified by chromatography and crystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1-[Trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-3,4,5-trifluorobenzene (2.1 g) was obtained from <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)cyclohexanone</strong> (2.2 g) and 1-bromo-3,4,5-trifluorobenzene (2.0 g) in the same manner as in Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; thiourea;trimethyleneglycol; In tetrahydrofuran; methanol; toluene; Petroleum ether; | EXAMPLE 3 A solution of 34 g of 1-(2-p-methoxyphenyl-ethyl)-4-(trans-4-propylcyclohexyl)-cyclohexene [obtainable by reaction of 2-p-methoxyphenyl-ethyl-magnesium bromide with <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)-cyclohexanone</strong> and subsequent hydrolysis to 1-(2-p-methoxyphenyl-ethyl)-4-(trans-4-propylcyclohexyl)-cyclohexanol and dehydration with p-toluenesulfonic acid in boiling toluene] in 600 ml of THF is hydrogenated on 5 g of PdO at 40 under 1 bar until the reaction stops. The mixture is filtered, the filtrate is evaporated, the residue is taken up in 200 ml of boiling methanol and the resulting hot solution is poured into a boiling solution of 70 g of thiourea in 300 ml of methanol. The mixture is cooled to 0 and the thiourea-inclusion compound precipitated is filtered off and boiled up with 350 ml of petroleum ether (boiling point 40-60). The undissolved residue is warmed at 50 with 350 ml of 2N aqueous potassium hydroxide solution for 30 minutes. The resulting solution is acidified with 10% H2 SO4 and the trans/trans-4-(2-p-methoxyphenyl-ethyl)-4'-propylbicyclohexyl which was precipitated is filtered off. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; potassium hydrogen sulphate; In tetrahydrofuran; nitrogen; toluene; | EXAMPLE 26 Preparation of 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexen-1-yl]benzene (a compound of the formula (X) wherein R is propyl) A solution of p-dibromobenzene (5.6 g, 0.024 mol) dissolved in tetrahydrofuran (200 ml) was dropwise added to sliced Mg (1.2 g, 0.049 mol) in nitrogen current so as to give soft reflux. After 7 hours, the reaction finished to yield its magnesium bromide, to which a solution of <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)-cyclohexanone</strong> (10.9 g, 0.049 mol) dissolved in tetrahydrofuran (100 ml) was rapidly dropwise added while the temperature was kept at 30 C. or lower. After the addition, the mixture was refluxed for 1.5 hour and 3N hydrochloric acid was added. The reaction liquid was extracted with toluene (100 ml*3), combined toluene layers were washed with water and the solvent was distilled off under reduced pressure. The remaining oily substance was 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexan-1-ol]benzene, to which potassium hydrogen sulfate (2.5 g) was added, followed by dehydrating at 200 C. for 2 hours in nitrogen current, cooling, adding toluene (300 ml), filtering off potassium hydrogen sulfate, washing toluene layer with water, distilling off the solvent under reduced pressure and recrystallizing the residue from toluene to obtain an objective product, 1,4-bis[4-(trans-4-propylcyclohexyl)cyclohexen-1-yl]benzene (yield: 0.9 g) having a C-Sm point of 98.5 C. and a Sm-I point of 300 C. or higher. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; n-heptane; nitrogen; magnesium; toluene; | Example 1 Synthesis of 4-(trans-4-n-propylcyclohexyl)-[2-(4-methylphenyl)ethyl]cyclohexene [Compound No. 1 (in the formula [Iaa], X11 = methyl, Y = H, and R = n-propyl)]: In a nitrogen gas stream, 30 ml of a THF solution containing 6.6 g of 2-(4-methylphenyl)ethyl bromide was added dropwise at 20C into a three-necked flask in which 0.9 g of magnesium and 5 ml of THF were present. Afterward, the solution was stirred for 1 hour, and 20 ml of a THF solution containing 6.7 g of <strong>[82832-73-3]4-(trans-4-n-propylcyclohexyl)cyclohexanone</strong> was then added dropwise thereto at 20C. After stirring for 5 hours, the solution was cooled to 0C, and 50 ml of 6 N hydrochloric acid and 50 ml of toluene were then added thereto. After the removal of a water layer, the solution was washed with 50 ml of a 1 N aqueous sodium hydroxide solution, and water washing was continued until the aqueous solution had become neutral. The resulting toluene solution was dried over anhydrous magnesium sulfate and then concentrated. Afterward, 0.3 g of p-toluenesulfonic acid and 20 ml of toluene were added thereto, followed by heating under reflux for 1 hour. At this time, a drainage pipe was used to remove water formed by azeotropy. The solution was then cooled to 20C, and 50 ml of a 0.5 N aqueous sodium hydroxide solution and 50 ml of heptane were added thereto, followed by removing a water layer. Afterward, the solution was washed with 50 ml of a saturated sodium chloride solution three times, and then dried over anhydrous magnesium sulfate and concentrated. The thus treated solution was passed through an alumina-packed column by the use of a heptane solvent, and the used heptane was then distilled off, followed by distillation, whereby 6.2 g of white crystals was obtained. The thus obtained crystals were further recrystallized from a hexane solvent and then dried in order to prepare 3.2 g of the desired compound. The chemical structure of the product was confirmed by NMR. m.p. 46C and clp. 120C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 9 Synthesis of 4-(trans-4-n-propylcyclohexyl)-[2-(4-fluorophenyl)ethyl]cyclohexene [Compound No. 241 (in the formula [Iac], Y = H and R = propyl): The same procedure as in Example 1 was effected except that 2-(4-methylphenyl)ethyl bromide used in Example 1 was replaced with 2-(4-fluorophenyl)ethyl bromide and then reacted with <strong>[82832-73-3]4-(trans-4-n-propylcyclohexyl)cyclohexanone</strong>, in order to obtain the desired compound. m.p. 25C and clp. 95C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; n-heptane; nitrogen; magnesium; toluene; | Example 5 Synthesis of 4-(trans-4-n-propylcyclohexyl)-[2-(3-fluoro-4-n-propylphenyl)ethyl]cyclohexene [Compound No. 121 (in the formula [Iaa], X11 = propyl and Y = F]: In a nitrogen gas stream, 30 ml of a THF solution containing 8.1 g of 2-(3-fluoro-4-n-propylphenyl)ethyl bromide was added dropwise at 20C into a three-necked flask in which 0.9 g of magnesium and 5 ml of THF were present. Afterward, the solution was stirred for 1 hour, and 20 ml of a THF solution containing 6.7 g of <strong>[82832-73-3]4-(trans-4-n-propylcyclohexyl)cyclohexanone</strong> was then added dropwise thereto at 20C. After stirring for 5 hours, the solution was cooled to 0C, and 50 ml of 6 N hydrochloric acid and 50 ml of toluene were then added thereto. After the removal of a water layer, the solution was washed with 50 ml of a 1 N aqueous sodium hydroxide solution, and water washing was continued until the aqueous solution had become neutral. The resulting toluene solution was dried over anhydrous magnesium sulfate and then concentrated. Afterward, 0.3 g of p-toluenesulfonic acid and 20 ml of toluene were added thereto, followed by heating under reflux for 1 hour. At this time, a drainage pipe was used to remove water formed by azeotropy. The solution was then cooled to 20C, and 50 ml of a 0.5 N aqueous sodium hydroxide solution and 50 ml of heptane were added thereto, followed by removing a water layer. Afterward, the solution was washed with 50 ml of a saturated sodium chloride solution three times, and then dried over anhydrous magnesium sulfate and concentrated. The thus treated solution was passed through a alumina-packed column by the use of a heptane solvent, followed by distillation, whereby 7.6 g of white crystals was obtained. The thus obtained crystals were further recrystallized from a hexane solvent and then dried in order to prepare 3.9 g of the desired compound. The chemical structure of the product was confirmed by NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; | First Step A mixture of 531 g (1170 mmol) of 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium bromide and 4.0 l of THF was cooled to -30 C. under a nitrogen gas stream with a refrigeration medium. To this mixture, 121 g (1080 mmol) of t-BuOK was added, followed by stirring for 1 hour. Furthermore, 1 l of a THF solution containing 200 g (899 mmol) of <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)cyclohexanone</strong> was added dropwise to the mixture, while the temperature was maintained at -30 C. or less. After the dropping, the reaction temperature was slowly raised to room temperature, and the solution was further stirred for 5 hours. Next, the reaction solution was filtered through Celite, and the solvent was then distilled off under reduced pressure. The resulting residue was purified through silica gel column chromatography (a developing solvent: a mixed solvent of toluene/ethyl acetate=9/1 (v/v)) to obtain 277 g of crude 2-(2-(4-(trans-4-propylcyclohexyl)cyclohexylidene)ethyl)-1,3-dioxane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; magnesium; In tetrahydrofuran; water; | Second Step Preparation of 3,4-difluoro-5-ethoxy-(1hydroxy-4-(trans-4-propylcyclohexyl)cyclohexyl)benzene To a 500 ml three neck flask provided with a stirrer, thermometer, and nitrogen gas introducing tube were added 2.7 g (110.8 mmol) of magnesium turnings and 20 ml of tetrahydrofuran (hereinafter abbreviated as THF) under nitrogen gas atmosphere, and 60 ml of solution of 23.3 g (105.5 mmol) of the 3,4-difluoro-5-ethoxybromobenzene obtained in the first step in THF was added dropwise thereto in 50 minutes while being adjusted so that the reaction temperature did not exceed 50 C. After finishing of the dropping, it was further stirred for 2 hours while being heated at 50 C. Then, 60 ml of solution of 23.5 g (105.5 mmol) of <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)cyclohexanone</strong> in THF was added dropwise thereto in 30 minutes with the reaction temperature being adjusted at 45 to 50 C., and further stirred at 50 C. for 2 hours. After the reaction mixture was cooled down to a temperature lower than 5 C., 30 ml of 6N hydrochloric acid was added thereto. Subsequently, it was extracted with 200 ml of toluene, and the extract was washed with water (150 ml) twice, with 100 ml of saturated aqueous sodium carbonate solution once, and with water (150 ml) twice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure to obtain 43.9 g of a brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium; In tetrahydrofuran; water; | (1-1) Synthesis of 2,3,4-trifluoro-1-[1-hydroxy-4-(trans-4-propylcyclohexyl) cyclohexyl]benzene Into 7.6 g of magnesium and 20 mL of THF which were stirred while water-cooling in a nitrogen atmosphere, a THF solution (200 mL) containing 60 g of 2,3,4-trifluorobromobenzene was added dropwise for 2 hours, and stirred for 3 hours. Into this, a THF solution (200 mL) containing 70 g of <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)cyclohexanone</strong> was added dropwise for 2 hours, and stirred for 2 hours. After the reaction solution was poured into 10% hydrochloric acid and stirred for a while, an organic layer was separated, and an aqueous layer was extracted with toluene. After the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure to obtain 110 g of 2,3,4-trifluoro-1-[1-hydroxy-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene (unsatisfactorily dried). MS m/z: 354 (M+), 55 (100) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31.0 g (0.17 mol) of 1-butoxy-2,3-difluorobenzene are initially introduced in 200 ml of THF, and 100 ml (0.16 mol) of n-BuLi (15% soln. in hexane) are added at -70 C. After 2 h at this temperature, a solution of 35.6 g (0.16 mol) of <strong>[82832-73-3]4'-propylbicyclohexyl-4-one</strong> in 200 ml of THF is metered in, and the batch is stirred for 2.5 h. The reaction mixture is hydrolysed with ice-cooling and acidified using 2 N HCl. The solution is extracted with MTBE, and the combined organic phases are washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product (66.3 g of yellow solid) is used directly for the following reaction. 6.2 4-(4-Butoxy-2,3-difluorophenyl)-4'-propylbicyclohexyl-3-ene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium sulfate; In tetrahydrofuran; toluene; | (1-1) In a nitrogen atmosphere, metal magnesium (5.5 g) was suspended in THF (5 mL), a solution prepared by dissolving 3,5-difluorobromobenzene (41.5 g) in THF (120 mL) was added at a rate at which the solution was gently refluxed, and stirring was performed at 40 C. for 45 minutes. Subsequently, a solution prepared by dissolving <strong>[82832-73-3]4-(trans-4-propylcyclohexyl)cyclohexanone</strong> (39.8 g) in THF (85 mL) was added at 40 C., and then stirring was performed at room temperature for one hour. The reaction liquid was gently added under stirring to 10% hydrochloric acid (120 mL) cooled to 5 C., and toluene (160 mL) was added thereto and extraction was performed. The resulting organic layer was washed with a saturated saline solution (120 mL). Anhydrous sodium sulfate was added to perform drying. The organic solvent was distilled off under reduced pressure to obtain a crude 3,5-difluoro-4-(1-hydroxy-4-(4-trans-propylcyclohexyl)cyclohexyl)benzene (62.5 g). |
Tags: 82832-73-3 synthesis path| 82832-73-3 SDS| 82832-73-3 COA| 82832-73-3 purity| 82832-73-3 application| 82832-73-3 NMR| 82832-73-3 COA| 82832-73-3 structure
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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 |
Sorry,this product has been discontinued.
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