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CAS No. : | 2142-06-5 | MDL No. : | MFCD00516834 |
Formula : | C11H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IONNJVQITCVNHK-UHFFFAOYSA-N |
M.W : | 189.21 | Pubchem ID : | 95241 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.73 |
TPSA : | 37.38 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) : | -7.0 cm/s |
Log Po/w (iLOGP) : | 1.89 |
Log Po/w (XLOGP3) : | 0.64 |
Log Po/w (WLOGP) : | 0.8 |
Log Po/w (MLOGP) : | 1.62 |
Log Po/w (SILICOS-IT) : | 2.0 |
Consensus Log Po/w : | 1.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.6 |
Solubility : | 4.74 mg/ml ; 0.025 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.0 |
Solubility : | 18.9 mg/ml ; 0.0999 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.03 |
Solubility : | 0.178 mg/ml ; 0.00094 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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 |
---|---|---|
57% | With sodium tetrahydroborate; In methanol; dichloromethane; at 0℃; for 2h; | To a 0 C solution of <strong>[2142-06-5]N-benzylsuccinimide</strong> 3 (3 g, 16 mmol) in CH2Cl2-MeOH (80 mL, 1 : 3), NaBH4 (1.5 g, 40 mmol) was added portionwise over a period of 2 h with stirring. Then water (50 mL) was added and the volatiles were removed in vacuo. The precipitate formed was collected by filtration, washed with water and air-dried. The filtrate was extracted with dichloromethane, dried with MgSO4, and the solvent was removed in vacuo to give the addition crop of the target product. The products were combined and recrystallized from benzene. White powder, m.p.110-111 C (cf. Ref. 26: m.p. 105-106 C), yield 1.73 g (57%). 1H NMR (CDCl3), delta: 1.84-1.97 (m, 1 H, C(O)CH2CHaHb); 2.16-2.39 (m, 2 H, C(O)CH2); 2.50-2.70 (m, 1 H,C(O)CH2CHaHb); 4.27 (d, 1 H, OH, J = 7.8 Hz); 4.17 (d, 1 H, NCHaHbPh, J = 14.8 Hz); 4.85 (d, 1 H, NCHaHbPh, J = 14.8 Hz); 5.03-5.12 (m, 1 H, CH); 7.22-7.38 (m, 5 H, Ph). 13C NMR (CDCl3), delta: 28.10, 29.00, 43.42, 82.47, 127.67, 128.35, 128.76, 136.55, 174.98. |
50% | With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0℃; for 3h; | N-benzylsuccinamidal: Powered sodium borohydride (0.5 g, 10.75 mmol) was added portionwise to a stirred solution of <strong>[2142-06-5]N-benzylsuccinimide</strong> (1.0 g, 5 mmol) in 1:1 tetrahydrofuran-ethanol (15 mL) at 0 C. After 3 h, the reaction was quenched by the addition of 10% aqueous hydrochloric acid (2.5 mL) and the mixture was diluted with water, extracted with ethyl acetate, and dried with Na2SO4 and concentrated. A solid was obtained which had m.p. 104-106 C after crystallization from ethyl acetate (0.65 g, 50%). 1H NMR (300 MHz, CDCl3) ppm 1.74-2.72 (m, 4 H), 4.15 (d, J = 15.1 Hz, 1 H), 4.84 (d, J = 15.1 Hz, 1 H), 5.07 (dd, J = 2.1 Hz, 4.2 Hz, 1 H), 7.30 (s, 5 H). Anal. Calcd for C11H13NO2: C 69.09 H 6.85 N 7.32; found: C 69.12, H 6.78, N 7.17. IR (KBr, cm-1) 3355, 1685 (C=O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With ammonium peroxodisulfate; In 1,4-dioxane; dimethyl sulfoxide; at 100℃; for 7h; | General procedure: A solution of amine (1 equiv) and anhydride (1.1 equiv) in 1,4-dioxane was stirred at room temperature (or 100 C if necessary) in a two neck round bottom flask equipped with a water condenser. As soon as all the amine converts to the corresponding amic acid (monitored by TLC), ammonium persulfate [(NH4)2S2O8] (2 equiv) and DMSO (2 equiv) were added and the reaction mixture was heated to 100 C. Heating was continued at the same temperature until completion (3-10 h) of the reaction. After completion, the reaction mixture was filtered through a cotton plug and dioxane was removed under vacuo. The residue was dissolved in ethyl acetate and washed with dilute HCl, saturated aqueous NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and evaporated under vacuo to furnish the corresponding imides in good to excellent yields with more than 98% purity (GC, NMR). |
92% | With sodium acetate; acetic anhydride; for 2h;Reflux; | To N-benzylsuccinic acid monoamide, calcined sodium acetate (1.02 g, 12.15 mmol) and acetic anhydride (50 mL) were added and the mixture was refluxed for 2 h. Removal of the solvent in vacuo and recrystallization of the residue from diethyl ether afforded N-benzylsuccinimide (3), white crystals, m.p. 96-98 C (cf. Ref. 26: m.p. 102-103 C), yield 8.7 g (92%). 1H NMR (CDCl3), delta: 2.68 (s, 4 H, 2 CH2); 4.65 (s, 2 H, PhCH2); 7.28-7.39 (m, 5 H, Ph). |
With sodium acetate; acetic anhydride; for 2h;Reflux; | General procedure: The synthesis of maleimides 1-47 was performed by mixing an equimolar amount of the appropriate maleic anhydrides 68-72 in 5 mL of CHCl3 and anilines 73, 78-90, amines 91-94 or phenylalkylamines 74-77 (5 mmol) dissolved in 1 mL of CHCl3 and stirred during 1 h. The solid (maleamic acid) which precipitated out of the reaction mixture was filtered off. The whole amount of maleamic acid was dissolved in 5 mL of acetic anhydride and 100 mg of sodium acetate was added. The mixture was heated for 2 h under reflux. The reaction was cooled and quenched with water; then, the aqueous solution was extracted with Et2O, dried with Na2SO4, filtered, and the solvent was evaporated. The product was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (9:1) as eluent. Compounds 1-10, 16-26, 31-34, 36, 38-42 and 43-47 were previously reported.[3], [8], [21], [22], [23], [24], [25], [26], [27] and [28] |
With sodium acetate; acetic anhydride; for 0.5h; | General procedure: In a 100 mL three-necked flask provided with a stirrer, a reflux condenser, and adropping funnel were placed 2.0 g (20 mmol) of succinic anhydride and 25 mL of diethylether. The succinic anhydride dissolved upon stirring, at which point a solution of 1equiv. (20 mmol) of the corresponding amine in 5 mL of diethyl ether was run throughthe dropping funnel. The resulting thick suspension was stirred at room temperature for 1h and was then cooled in an ice bath. The N-substituted succinamic acid was recoveredby filtration and dried. The residue was then added to a flask containing a solution ofanhydrous sodium acetate (0.65 g, 8 mmol) in acetic anhydride (6.7 mL) and stirred overa steam bath for 30 min. The reaction mixture was then cooled to room temperature in acold water bath and was then poured into 100 mL of an ice-water mixture. Theprecipitated product was recovered by filtration, washed three times with 30 mL portionsof ice-cold water, and dried. The crude N-substituted succinimide was recrystallized fromethanol/water to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; sodium t-butanolate; In isopropyl alcohol; at 40℃; under 30003.0 Torr; for 12h;Autoclave; Sealed tube; | Add 38 mg of <strong>[2142-06-5]1-benzylpyrroline-2,5-dione</strong> (0.2 mmol), 2.2 mg of sodium tert-butoxide, and 2 ml of isopropanol under nitrogen protection. Add 5 mul of 0.001 M catalyst (S / C = 40,000), then the reaction flask was transferred to an autoclave, the reaction kettle was tightened, 4 MPa of hydrogen was charged, and the reaction was carried out at 40 C for 12 hours. After the reaction was completed, the mixture was naturally cooled to room temperature, and the hydrogen was carefully released. The celite was filtered, and the organic solvent was removed from the filtrate to obtain 38 mg of a yellow oil with a yield of 99%. |
Tags: 2142-06-5 synthesis path| 2142-06-5 SDS| 2142-06-5 COA| 2142-06-5 purity| 2142-06-5 application| 2142-06-5 NMR| 2142-06-5 COA| 2142-06-5 structure
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