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CAS No. : | 5978-70-1 | MDL No. : | MFCD00064284 |
Formula : | C8H18O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SJWFXCIHNDVPSH-MRVPVSSYSA-N |
M.W : | 130.23 | Pubchem ID : | 80080 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.73 |
TPSA : | 20.23 Ų |
GI absorption : | High |
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) : | -5.04 cm/s |
Log Po/w (iLOGP) : | 2.54 |
Log Po/w (XLOGP3) : | 2.9 |
Log Po/w (WLOGP) : | 2.34 |
Log Po/w (MLOGP) : | 2.22 |
Log Po/w (SILICOS-IT) : | 1.97 |
Consensus Log Po/w : | 2.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.14 |
Solubility : | 0.934 mg/ml ; 0.00717 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.99 |
Solubility : | 0.135 mg/ml ; 0.00103 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.12 |
Solubility : | 0.999 mg/ml ; 0.00767 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.9 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H227-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 trichloroisocyanuric acid; In dichloromethane; at 25℃; for 0.133333h;Sonication; Green chemistry; | General procedure: c) Dehydrohalogenation reaction using TCCA-DMFreagent under sonication: Methodology for the ultrasonicallyassisted dehydrohalogenation of alcohols by TCCA-DMF under sonication is by and large similar to the classical method. One mole of the prepared TCCA-DMF reagent and one mole of alcohol were placed in a reaction flask and clamped in a Sonicator. Progress of the reaction was checked by TLC till the completion of the reaction. After completion of the reaction as ascertained by TLC,similar work up procedure mentioned in the above section (classical method) is adopted to the alkyl chloride product. Products obtained were characterized by spectroscopic methods. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine chloroacetic acid-<l-octyl-(2)-ester>; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: (R)-Octan-2-ol; diethyl N-tert-butyloxycarbonylphosphoramidate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20 - 25℃; for 2h; Stage #2: toluene-4-sulfonic acid In ethanol for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | pyridinium p-toluenesulfonate; In dichloromethane; at 0 - 20℃; for 0.5h; | A solution of 66.3 mg (0.24 mmol) of the compound (15) in 1 ml of methylene chloride was added dropwise to a solution of 26.0 mg (0.2 mmol) of (R)-(-)-2-octanol containing 5.0 mg (0.02 mmol) of pyridinium p-toluenesulfonate (PPTS) at 0C. The mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with saturated brine, dried over anhydrous potassium carbonate, and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 19: 1) to obtain 76.6 mg (0.189 mmol, 94%) of a compound (16) as a colorless oil. The compound was separated into diastereomers by silica gel column chromatography (n-hexane: ethyl acetate = 1: 3) to obtain two types of optically active compounds of 16a and 16b. The yields of 16a and 16b are respectively 29.1 mg (38%) and 32.2 mg (42%). The properties data of the resulting compounds (16a and 16b) are shown as follows. (16a: 8-diphenylmethyl-7-[(2'R)-2'-octyloxy]-bicyclo[3.3.0]-1-oxaoctane)1H-NMR (CDCl3, deltappm): 7.41 (brd, J= 7.6 Hz, 4H), 7.28-7.08 (m, 6H), 4.57 (s, 1H), 3.94 (tq, J = 6.0, 6.0 Hz, 1H), 3.84 (t, J = 7.2 Hz, 2H), 2.67 (ddd, J = 6.2, 9.2, 13.6 Hz, 1H), 1.96 (t, J = 7.2 Hz, 2H), 1.84-1.70 (m, 2H), 1.68-1.25 (m, 11H), 1.20 (d, J = 6.0 Hz, 3H), 1.13-0.98 (m, 1H), 0.94 (ddd, J = 9.5, 9.5, 12.0 Hz, 1H), 0.89 (t, J = 6.5 Hz, 3H) Elemental analysis: Calcd for C28H38O2: C, 82.71; H, 9.42. Found: C, 82.49; H, 9.64 (%) Optical rotation: [alpha]D22 = -152.94 (c = 2.21, CHCl3) (16b: 8-diphenylmethyl-7-[(2'S)-2'-octyloxy]-bicyclo[3.3.0]-1-oxaoctane)1H-NMR (CDCl3, deltappm): 7.41.(brd, J= 7.6Hz, 4H), 7.28-7.08 (m, 6H), 4.55 (s, 1H), 3.85 (tq, J = 6.0, 6.0 Hz, 1H), 3.88-3.76 (m, 2H), 2.63 (ddd, J = 6.2, 8.8, 13.6 Hz, 1H), 1.99 (ddd, J = 8.0, 8.0, 12.0 Hz, 1H), 1.93 (ddd, J = 5.3, 6.7, 12.0 Hz, 1H), 1.88-1.71 (m, 2H), 1.70-1.29 (m, 11H), 1.19 (d, J = 6.0 Hz, 3H), 1.13-0.89 (m, 2H), 0.92 (t, J = 6.5 Hz, 3H) Elemental analysis: Calcd for C28H38O2: C, 82.71; H, 9.42. Found: C, 82.49; H, 9.71 (%) Optical rotation: [alpha]D22 = +118.59 (c = 2.27, CHCl3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
972 mg (76%) | With diethylazodicarboxylate | PNA Intermediates (S)-4-(1-Methylheptyloxy)-2-(nitro)-1-(benzyloxy)-benzene (55). DEAD (777 mg, 4.46 mmol), TPP (1.171 g, 4.46 mmol), R-2-octanol (511 mg, 3.93 mmol), and compound 54 (875 mg, 3.57 mmol) were reacted according to the procedure for compound 32a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-80/20 (Hex/EtOAc). Evaporation of solvent yielded 972 mg (76%) of a light yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; thionyl chloride; In hexane; toluene; | A mixture of 59 g of <strong>[114045-96-4]2-fluoro-4-benzyloxybenzoic acid</strong> and 70 ml of thionyl chloride was heated for 6 hours on a water bath maintained at 50 C. Excessive thionyl chloride was distilled away under reduced pressure. On cooling with water, solids were formed. These solids were dispersed in hexane and then filtered to obtain 61 g of solid. This was <strong>[114045-96-4]2-fluoro-4-benzyloxybenzoic acid</strong> chloride. 36 g of <strong>[114045-96-4]2-fluoro-4-benzyloxybenzoic acid</strong> chloride and 27 g of R-(-)-2-octanol were heated with stirring for 3 hours in an atmosphere of nitrogen. The reaction mixture was allowed to cool and then 200 ml of toluene was added. An organic layer was washed with saturated saline water, with 6 N hydrochloric acid, with saturated saline water, with a 2 N sodium hydroxide aqueous solution and then with saturated saline water to make it neutral. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 1'-methylheptyl 2-fluoro-4-benzyloxy-benzoate. | |
With hydrogenchloride; sodium hydroxide; thionyl chloride; In hexane; toluene; | A mixture of 59 g of <strong>[114045-96-4]2-fluoro-4-benzyloxybenzoic acid</strong> and 70 ml of thionyl chloride was heated for 6 hours on a water bath maintained at 50C. Excessive thionyl chloride was distilled away under reduced pressure. On cooling with water, solids were formed. These solids were dispersed in hexane and then filtered to obtain 61 g of solid. This was <strong>[114045-96-4]2-fluoro-4-benzyloxybenzoic acid</strong> chloride. 36 g of <strong>[114045-96-4]2-fluoro-4-benzyloxybenzoic acid</strong> chloride and 27 g of R-(-)-2-octanol were heated with stirring for 3 hours in an atmosphere of nitrogen. The reaction mixture was allowed to cool and then 200 ml of toluene was added. An organic layer was washed with saturated saline water, with 6 N hydrochloric acid, with saturated saline water, with a 2 N sodium hydroxide aqueous solution and then with saturated saline water to make it neutral. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 1--methylheptyl 2-fluoro-4-benzyloxy-benzoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With tributylphosphine In dichloromethane at 20℃; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.6% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; sodium hydrogencarbonate at 37℃; Green chemistry; Enzymatic reaction; | 4.3.3. Lipase-catalyzed hydrolysis of esters (step 3) General procedure: The distillation residue of step 2 was mixed with a solution of sodium bicarbonate (0.60 mol/L, 90 ml) at 37 °C for 30 min. The hydrolysis of the enantiomerically enriched ester was started bythe addition of Novozyme 435 (0.3 g). Samples (0.5 mL) were withdrawn at regular intervals, extracted with n-hexane (1.5 mL) and analyzed as described above. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: To a solution of a secondary alcohol (0.177 mmol) in dry THF (0.5 mL) was added dropwise n-BuLi (1.59 mol/L in hexane, 0.1 mL, 0.159 mmol, at -5 C) under a nitrogen atmosphere. After being stirred for 30 min, a solution of (R)-3 or (S)-3 (34.3 mg, 0.177 mmol) was added slowly to the mixture. After 15 min, the reaction was quenched with a saturated aqueous NH4Cl solution (1 mL), and then water (5 mL) and Et2O (10 mL) were added to the reaction mixture. The organic layer was separated, washed with 2% HCl (5 mL), water (5 mL), and a saturated aqueous NaHCO3 solution (5 mL), and dried over MgSO4. The solvent was evaporated and the residue was purified by column chromatography (hexane/AcOEt = 19:1) to give 1-fluoroindan-1-carboxylic acid ester with a secondary alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | General procedure: To a solution of a secondary alcohol (0.177 mmol) in dry THF (0.5 mL) was added dropwise n-BuLi (1.59 mol/L in hexane, 0.1 mL, 0.159 mmol, at -5 C) under a nitrogen atmosphere. After being stirred for 30 min, a solution of (R)-3 or (S)-3 (34.3 mg, 0.177 mmol) was added slowly to the mixture. After 15 min, the reaction was quenched with a saturated aqueous NH4Cl solution (1 mL), and then water (5 mL) and Et2O (10 mL) were added to the reaction mixture. The organic layer was separated, washed with 2% HCl (5 mL), water (5 mL), and a saturated aqueous NaHCO3 solution (5 mL), and dried over MgSO4. The solvent was evaporated and the residue was purified by column chromatography (hexane/AcOEt = 19:1) to give 1-fluoroindan-1-carboxylic acid ester with a secondary alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 99 % ee 2: 8 % ee 3: 11 % ee 4: 77 % ee | With lipase B from Candida antarctica In toluene at 78℃; for 48h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 99 % ee 2: 3 % ee 3: 7 % ee 4: 87 % ee | With lipase B from Candida antarctica In toluene at 78℃; for 48h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: ethyl 4-hydroxy-4-biphenyl carboxylate With triphenylphosphine In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: (R)-Octan-2-ol With diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 5 - 20℃; | Diisopropyl azodicarboxylate (3.76 mmol) was added during ten to fifteen minutes to the stirred mixture of 3'-chloro-4"-hydroxy-4-(trans-4-heptylcyclohexyl)terphenyl of Intermediate 3(3.26 mmol), R-2-octanol (3.76 mmol) and triphenylphosphine (3.76 mmol) in 20 ml of THF at a temperature between 5 C. and 10 C. The mixture was allowed to stir overnight at room temperature. THF was then distilled out in vacuo and the residue was several times washed with hexane to extract the desired product. The product was purified by flash chromatography on aluminum oxide (hexane-ethyl acetate, 50:1) followed by the crystallisation from 2-propanol. The yield was 57%. |
Tags: 5978-70-1 synthesis path| 5978-70-1 SDS| 5978-70-1 COA| 5978-70-1 purity| 5978-70-1 application| 5978-70-1 NMR| 5978-70-1 COA| 5978-70-1 structure
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Code | Phrase |
H400 | Very toxic to aquatic life |
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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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