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CAS No. : | 84418-43-9 | MDL No. : | MFCD00237376 |
Formula : | C15H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZZOKVYOCRSMTSS-UHFFFAOYSA-N |
M.W : | 239.27 | Pubchem ID : | 736301 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.13 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 68.88 |
TPSA : | 52.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 2.2 |
Log Po/w (XLOGP3) : | 2.89 |
Log Po/w (WLOGP) : | 2.89 |
Log Po/w (MLOGP) : | 2.53 |
Log Po/w (SILICOS-IT) : | 2.56 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.087 mg/ml ; 0.000363 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.65 |
Solubility : | 0.0537 mg/ml ; 0.000224 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.7 |
Solubility : | 0.00481 mg/ml ; 0.0000201 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.96 |
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 |
---|---|---|
Fmoc amine 15: Amine 3 (2.73 g, 10 mol) was dissolved in a mixture of THF/water (40:10) and cooled in an ice bath. Fmoc-NHS ester (5.1 g, 15 mmol) was added as a solid followed by solid sodium bicarbonate (1.34 g, 15 mmol). The reaction mixture was stirred for 20 h at RT. The solution was diluted with 100 ml of EtOAc and washed with saturated sodium bicarbonate (2*50 ml), water (1*100 ml) and dried (sodium sulfate). Evaporation of the solvent followed by chromatography of the crude product on flash silica gel (200.0 g) yielded the product as a colorless paste (6:4 hexane:EtOAc). Yield: 3.2 g (65%). Rf: 0.38 (1:1 EtOAc/Hexane). 1H NMR (CDCl3) delta (2S, 18H, Methyls), 2.25 (t, 2H, -COCH2), 2.5 (t, 2H, COCH2), 3.4 (t, 2H, N-CH2), 3.5 (t, 2H, N-CH2), 4.25 (t, 1H, Ar-CH), 4.5 (d, 2H, O-CH2), 7.25 (m, 2H, Ar-H), 7.4 (m, 2H, Ar-H), 7.6 (d, 2H, Ar-H) and 7.75 (d, 2H, Ar-H). MS m/z 518.3 [M+Na]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; ethyl acetate; acetonitrile; | Anisomycin 19 (0.5 g 1.88 mmol) was suspended in 15 mL of acetonitrile. 9-Fluorenylmethyl succinimide (0.762 g 2.26 mmol) was added to the suspension. Upon addition, all solid dissolved. After stirring for 16 hours at room temperature, water was added to the reaction solution, and it was extracted with ethyl acetate. The organics were combined and dried over sodium sulfate. After filtration and concentration, purification was accomplished by column chromatography using 3:1 hexanes:ethyl acetate as the mobile phase. This gave 9-fluorenylmethyl carbamate 20 as foam in quantitative yields (0.916 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tin(IV) chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A. Primary amines (1.0 equiv) and substituted 3-ethoxycyclobutanonesa,b (1.5 equiv) were dissolved in anhydrous dichloromethane in a round bottom flask. Then, SnCl4 (0.05 equiv) was added into the reaction solution. The reaction mixture was kept stirring at room temperature under atmosphere of Argon for 0.5-1.0 h. The reaction was monitored by TLC and LC-MS. After completion of the reaction, Et3N was added to quench the reaction. The reaction mixture was diluted with dichloromethane and washed once with saturated aqueous NaHCO3 and once with water. Then organic layer was dried over MgSO4 and concentrated on rotavapor under reduced pressure. Finally the residue was purified by silical gel column chromatography to give corresponding beta-enamino ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tin(IV) chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A. Primary amines (1.0 equiv) and substituted 3-ethoxycyclobutanonesa,b (1.5 equiv) were dissolved in anhydrous dichloromethane in a round bottom flask. Then, SnCl4 (0.05 equiv) was added into the reaction solution. The reaction mixture was kept stirring at room temperature under atmosphere of Argon for 0.5-1.0 h. The reaction was monitored by TLC and LC-MS. After completion of the reaction, Et3N was added to quench the reaction. The reaction mixture was diluted with dichloromethane and washed once with saturated aqueous NaHCO3 and once with water. Then organic layer was dried over MgSO4 and concentrated on rotavapor under reduced pressure. Finally the residue was purified by silical gel column chromatography to give corresponding beta-enamino ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tin(IV) chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A. Primary amines (1.0 equiv) and substituted 3-ethoxycyclobutanonesa,b (1.5 equiv) were dissolved in anhydrous dichloromethane in a round bottom flask. Then, SnCl4 (0.05 equiv) was added into the reaction solution. The reaction mixture was kept stirring at room temperature under atmosphere of Argon for 0.5-1.0 h. The reaction was monitored by TLC and LC-MS. After completion of the reaction, Et3N was added to quench the reaction. The reaction mixture was diluted with dichloromethane and washed once with saturated aqueous NaHCO3 and once with water. Then organic layer was dried over MgSO4 and concentrated on rotavapor under reduced pressure. Finally the residue was purified by silical gel column chromatography to give corresponding beta-enamino ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tin(IV) chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A. Primary amines (1.0 equiv) and substituted 3-ethoxycyclobutanonesa,b (1.5 equiv) were dissolved in anhydrous dichloromethane in a round bottom flask. Then, SnCl4 (0.05 equiv) was added into the reaction solution. The reaction mixture was kept stirring at room temperature under atmosphere of Argon for 0.5-1.0 h. The reaction was monitored by TLC and LC-MS. After completion of the reaction, Et3N was added to quench the reaction. The reaction mixture was diluted with dichloromethane and washed once with saturated aqueous NaHCO3 and once with water. Then organic layer was dried over MgSO4 and concentrated on rotavapor under reduced pressure. Finally the residue was purified by silical gel column chromatography to give corresponding beta-enamino ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tin(IV) chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A. Primary amines (1.0 equiv) and substituted 3-ethoxycyclobutanonesa,b (1.5 equiv) were dissolved in anhydrous dichloromethane in a round bottom flask. Then, SnCl4 (0.05 equiv) was added into the reaction solution. The reaction mixture was kept stirring at room temperature under atmosphere of Argon for 0.5-1.0 h. The reaction was monitored by TLC and LC-MS. After completion of the reaction, Et3N was added to quench the reaction. The reaction mixture was diluted with dichloromethane and washed once with saturated aqueous NaHCO3 and once with water. Then organic layer was dried over MgSO4 and concentrated on rotavapor under reduced pressure. Finally the residue was purified by silical gel column chromatography to give corresponding beta-enamino ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tin(IV) chloride; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Procedure A. Primary amines (1.0 equiv) and substituted 3-ethoxycyclobutanonesa,b (1.5 equiv) were dissolved in anhydrous dichloromethane in a round bottom flask. Then, SnCl4 (0.05 equiv) was added into the reaction solution. The reaction mixture was kept stirring at room temperature under atmosphere of Argon for 0.5-1.0 h. The reaction was monitored by TLC and LC-MS. After completion of the reaction, Et3N was added to quench the reaction. The reaction mixture was diluted with dichloromethane and washed once with saturated aqueous NaHCO3 and once with water. Then organic layer was dried over MgSO4 and concentrated on rotavapor under reduced pressure. Finally the residue was purified by silical gel column chromatography to give corresponding beta-enamino ketone product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Example 2 Fmoc amination of 2,3,4-trioctadecanoxybenzhydrol To 2,3,4-trioctadecanoxybenzhydrol (650 mg, 657 mumol) obtained in Example 1 were added toluene (10 ml) and Fmoc-NH2 (189 mg, 790 mumol), and the mixture was warmed to 50C in an oil bath. Methanesulfonic acid (6.4 mul, 99 mumol) was added, and the mixture was heated to 100C and stirred for 6 hr. After confirmation of disappearance of a benzhydrol type anchor, the mixture was cooled to room temperature. Toluene (5 ml) and 5% aqueous sodium hydrogen carbonate (10 ml) were added and the mixture was stirred. After partitioning, the organic layer was further washed with water (10 ml*2). The organic layer was evaporated under reduced pressure, and the residue was washed with methanol (10 ml) to give N-Fmoc-[phenyl(2,3,4-trioctadecanoxyphenyl)methyl]amine (788 mg, yield 98%). 1H-NMR (CDCl3/300MHz) 0.88 (9H, t, J=6.6, C17H34-CH3) 1.10-1.65 (92H, br, Alkyl-H) 1.65-1.90 (4H, m, -O-CH2-CH2-C16H33) 3.40-3.50 (1H, br, m, -O-CH2-C17H35) 3.95 (5H, br, s, -O-CH2-C17H35) 4.25 (1H, br, s, fluorene C9-H) 4.40 (2H, br, m, fluorene-CH2-O) 5.85-5.95 (1H, br, Fmoc-NH- or Fmoc-NH-CH) 6.00-6.10 (1H, br, Fmoc-NH- or Fmoc-NH-CH) 6.61 (1H, br, d, J=8.7, Ph C5-H) 6.89 (1H, br, d, J=8.7, Ph C6-H) 7.10-7.50 (7H, br, m, Ph-H, fluorene C2,7-H) 7.55-7.65 (2H, br, fluorene C1,8-H) 7.70-7.82 (2H, br, fluorene C4,5-H) | |
98.1% | With methanesulfonic acid; In methanol; toluene; | (3) Synthesis of N-(9-fluorenylmethoxycarbonyl)-2,3,4-tris(octadecyloxy)benzhydryl amine Under an argon atmosphere, 2,3,4-tris(octadecyloxy)benzhydryl alcohol (2.44 g, 2.46 mmol) and <strong>[84418-43-9]9-fluorenylmethylcarbamate</strong> (1.06 g, 4.41 mmol) were dissolved in dehydrating toluene (40 mL) at 50 C., methanesulfonic acid (51.4 muL, 740 mol) was added, and the mixture was stirred at 100 C. overnight. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, methanol was added, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to give the title compound (3.37 g, 98.1%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With methanesulfonic acid; In toluene; at 100℃; for 3h; | 4-3: Fmoc amination of 4,4'-didocosoxybenzhydrol To 4,4'-didocosoxybenzhydrol (713 mg, 856 mumol) were added toluene (15 ml), Fmoc-NH2 (246 mg, 1.03 mmol) and methanesulfonic acid (8.3 mul, 128 mumol), and the mixture was stirred at 100C for 3 hr. After confirmation of disappearance of a benzhydrol type anchor, the mixture was cooled to room temperature. 2.5% Aqueous sodium hydrogen carbonate (10 ml) was added and the mixture was stirred. After partitioning, the organic layer was further washed with water (10 ml*2). The organic layer was evaporated under reduced pressure, and the residue was washed with methanol (10 ml) to give N-Fmoc-di(4-docosoxyphenyl)methylamine (540 mg, 512 mumol, yield 60%). 1H-NMR (CDCl3/300MHz) 0.88 (9H, t, J=6.6, C21H42-CH3) 1.10-1.50 (82H, br, Alkyl-H) 1.77 (4H, m, -O-CH2-CH2-C20H41) 3.93 (4H, d, J=6.6, -O-CH2-C21H43) 4.21 (1H, br, s, fluorene C9-H) 4.43 (2H, br, d, J=6.6, fluorene-CH2-O) 5.23 (1H, br, s, Fmoc-NH- or Fmoc-NH-CH) 5.85 (1H, br, s, Fmoc-NH- or Fmoc-NH-CH) 6.84 (4H, d, J=8.7, Ph C3,5-H) 7.11 (4H, d, J=8.7, Ph C2,6-H) 7.25-7.35 (2H, br, m, fluorene C2,7-H) 7.39 (2H, br, t, J= 6.9, fluorene C3,6-H) 7.59 (2H, br, s, fluorene C1,8-H) 7.75 (2H, br, d, J=6.6, fluorene C4,5-H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With methanesulfonic acid; In toluene; at 100℃; for 3.5h; | Example 18 Fmoc-amination of 4,4-di(12-docosoxydodecyloxy)benzhydrol To 4,4-di(12-docosoxydodecyloxy)benzhydrol (hereinafter OH-Dpm(OC12OC22), 482 mg, 401 mumol) were added toluene (10 ml), Fmoc-NH2 (101 mg, 422 mumol) and methanesulfonic acid (3.4 mul, 52.5 mumol), and the mixture was stirred at 100C for 3.5 hr. The reaction mixture was cooled to room temperature, 2.5% aqueous sodium hydrogen carbonate (6 ml) was added, and the mixture was stirred for a while. The aqueous layer was discarded, and the organic layer was washed with purified water (6 ml)*2. The organic layer was evaporated under reduced pressure, and the residue was crystallized from methanol to give Fmoc-NH-Dpm(OC12OC22) (533 mg, 374 mumol, 93%). 1H-NMR (CDCl3/300MHz) 0.88 (6H, t, J=6.9, C21H42-CH3) 1.15-1.65 (116H, br, Alkyl-H) 1.76 (4H, m, Ar-O-CH2-CH2-) 3.38 (8H, t, J=6.6, C11H22-CH2-O-CH2-C21H43) 3.93 (4H, t, J=6.6, Ar-O-CH2-C11H22) 4.21 (1H, br, s, fluorene C9-H) 4.43 (2H, br, m, fluorene-CH2-O) 5.23 (1H, br, Fmoc-NH- or Fmoc-NH-CH) 5.85 (1H, br, Fmoc-NH- or Fmoc-NH-CH) 6.84 (4H, d, J=8.7, Ph C3,5-H) 7.11 (4H, d, J=8.7, Ph C2,6-H) 7.25-7.35 (2H, br, fluorene C2,7-H) 7.39 (2H, br, fluorene C3,6-H) 7.59 (2H, br, fluorene C1,8-H) 7.75 (2H, br, fluorene C4,5-H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid; In toluene; | (1) Synthesis of N-(9-fluorenylmethoxycarbonyl)-bis(4-docosyloxyphenyl)methyl amine To 4,4'-bis(docosyloxy)benzhydrol (713 mg, 856 mummol) were added toluene (15 ml), <strong>[84418-43-9]9-fluorenylmethylcarbamate</strong> (246 mg, 1.03 mmol) and methanesulfonic acid (8.3 mul, 128 mumol), and the mixture was stirred at 100 C. for 3 hr. The disappearance of 4,4'-bis(docosyloxy)benzhydrol was confirmed, and the mixture was cooled to room temperature. 2.5% Aqueous sodium bicarbonate (10 ml) was added, and the mixture was stirred. The mixture was partitioned, and the organic layer was further washed with water (10 ml*2). The organic layer was evaporated under reduced pressure, and the residue was washed with methanol (10 ml) to give the title compound (540 mg, 512 mumol, yield 60%). 1H-NMR (CDCl3/300 MHz) delta 0.88 (9H, t, J=6.6, C21H42-CH3), 1.10-1.50 (82H, br, Alkyl-H), 1.77 (4H, m, -O-CH2-CH2-C20H41), 3.93 (4H, d, J=6.6, -O-CH2-C21H43), 4.21 (1H, br, s, fluorene C9-H), 4.43 (2H, br, d, J=6.6, fluorene-CH2-O), 5.23 (1H, br, s, Fmoc-NH- or Fmoc-NH-CH), 5.85 (1H, br, s, Fmoc-NH- or Fmoc-NH-CH), 6.84 (4H, d, J=8.7, Ph C3,5-H), 7.11 (4H, d, J=8.7, Ph C2,6-H), 7.25-7.35 (2H, br, m, fluorene C2,7-H), 7.39 (2H, br, t, J=6.9, fluorene C3,6-H), 7.59 (2H, br, s, fluorene C1,8-H), 7.75 (2H, br, d, J=6.6, fluorene C4,5-H) |
Tags: 84418-43-9 synthesis path| 84418-43-9 SDS| 84418-43-9 COA| 84418-43-9 purity| 84418-43-9 application| 84418-43-9 NMR| 84418-43-9 COA| 84418-43-9 structure
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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 |
Sorry,this product has been discontinued.
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