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* Storage: {[proInfo.prStorage]}
CAS No. : | 2162-74-5 | MDL No. : | MFCD00082211 |
Formula : | C25H34N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLDBGFGREOMWSL-UHFFFAOYSA-N |
M.W : | 362.55 | Pubchem ID : | 75100 |
Synonyms : |
|
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.48 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 120.39 |
TPSA : | 24.72 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -2.07 cm/s |
Log Po/w (iLOGP) : | 4.78 |
Log Po/w (XLOGP3) : | 9.07 |
Log Po/w (WLOGP) : | 8.32 |
Log Po/w (MLOGP) : | 6.13 |
Log Po/w (SILICOS-IT) : | 8.38 |
Consensus Log Po/w : | 7.33 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -7.73 |
Solubility : | 0.00000668 mg/ml ; 0.0000000184 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -9.48 |
Solubility : | 0.000000119 mg/ml ; 0.0000000003 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -8.3 |
Solubility : | 0.00000183 mg/ml ; 0.0000000051 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.05 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P270-P264-P301+P310+P330-P405 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
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 |
---|---|---|
65% | With iodine; triethylamine In ethyl acetate at 20℃; for 2.5 h; Inert atmosphere | To a stirring solution of DippN(H)C(S)N(H)Dipp (7.93g, 20.0mmol) and NEt3 (5.58mL, 40.0mmol) in ethyl acetate (100mL) was added I2 (5.58g, 22.0mmol) in portions over 30min. The mixture was stirred for 2h at room temperature then filtered to give a brown solution. Volatiles were removed under reduced pressure to give a brown solid. The solid was extracted with pentane (4×50mL), filtered through a silica plug and the resultant brown solution added to activated Cu (3.00g, 48.0mmol). The mixture was stirred for 16h at room temperature to give a black suspension. The suspension was filtered through silica to give a colourless solution. Volatiles were removed under reduced pressure and the resultant solid was dried in vacuo to afford 12 as a colourless crystalline solid. Yield: 4.74g (65percent). The 1H NMR spectrum was consistent with that reported by Cowley et al. [24]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.43 g (79%) | EXAMPLE 2 Synthesis of Bis(2,6diisopropylphenyl)carbodimide A mixture of 2.03 g (10 mmol) of 2,6-diisopropylphenylisocyanate and 10 mg (0.05 mmol) of 3-methyl-1-phenyl-3-phospholene-1-oxide were heated together at 100 C. under N2 for 48 h. The resultant oil was vacuum sublimed to provide 1.43 g (79%) of bis(2,6-diisopropylphenyl)carbodiimide as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In hexane; at 20℃;Schlenk technique; Inert atmosphere; | 1.35ml of 2M trimethylaluminium solution in hexanes was added to a solution of N,N?-bis(2,6-diisopropylphenyl)carbodiimide (0.891g, 2.4mmol) in 10ml of hexane at room temperature. The reaction mixture was stirred overnight with subsequent evaporation of hexane. 1.057g (99%) of pure white solid of 4 was obtained. Single crystals suitable for XRD analyses were obtained under argon from saturated solution of 4 in hexane at-30C. M.p. 129-130C. 1H NMR (C6D6, 500MHz, 295K) delta: 7.18 (m, 2H, ArH); 7.12 (m, 4H, ArH); 3.49 (m, 4H, CH); 1.30 (s, 3H, NC(CH3)N); 1.23 (d, 3J=7.0Hz, 12H, CH3); 1.20 (d, 3J=7.1Hz, 12H, CH3);-0.18 (s, 6H, AlCH3). 13C NMR (C6D6, 125MHz, 295K) delta: 176.6 (NCN); 145.2 (Ar); 138.7 (Ar); 127.0 (Ar); 124.3 (Ar); 28.9 (CH); 25.1 (CH3); 24.4 (CH3); 14.4 (NC(CH3)N);-9.0 (Al(CH3)2). Anal. Calcd for C28H43AlN2: C 77.38; H 9.97; N 6.45. Found: C 77.22; H 9.81; N 6.42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With iodine; triethylamine; In ethyl acetate; at 20℃; for 2.5h;Inert atmosphere; | To a stirring solution of DippN(H)C(S)N(H)Dipp (7.93g, 20.0mmol) and NEt3 (5.58mL, 40.0mmol) in ethyl acetate (100mL) was added I2 (5.58g, 22.0mmol) in portions over 30min. The mixture was stirred for 2h at room temperature then filtered to give a brown solution. Volatiles were removed under reduced pressure to give a brown solid. The solid was extracted with pentane (4×50mL), filtered through a silica plug and the resultant brown solution added to activated Cu (3.00g, 48.0mmol). The mixture was stirred for 16h at room temperature to give a black suspension. The suspension was filtered through silica to give a colourless solution. Volatiles were removed under reduced pressure and the resultant solid was dried in vacuo to afford 12 as a colourless crystalline solid. Yield: 4.74g (65%). The 1H NMR spectrum was consistent with that reported by Cowley et al. [24]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 55℃; for 6h;Inert atmosphere; | 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (5.16 g, 30 mmol) is dissolved in THF (40 ml) and hydrogenated in the presence of 0.08 g Pt (5% on carbon) catalyst using 4 bar hydrogen pressure. The hydrogen uptake stops after approximately one hour. The reaction mixture is then filtered and mixed with the solution of bis(2,6-diisopropylphenyl)carbodiimide (3.8 g, 10.5 mmol) in THF (30 ml). The solution is heated under argon at 550C for 6 hours, concentrated, the residue dissolved in dichloromethane (70 ml), washed with water (2 x 20 ml) and concentrated again. The residue is recrystallized from dichloromethane-ethyl acetate to afford 3.28 g of the title compound as a colorless solid, mp. 174-176 0C. 1H-NMR (CDCI3, 300 MHz): 7.3-6.8 (m, 6 ArH), 4.04-3.95 (m, 1 H, >CH-OH ), 3.52-3.42 (m, 2H, CHMe2), 3.27-3.18 (m, 2H, CHMe2), 2.0-1.40 (m, 4H, 2 x CH2), 1.43 (s, 6H, 2 x CH3), 1.27 (d, J=6.9Hz, 24H, 8 x CH3), 1.03 (s, 6H, 2 x CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
sodium hydroxide; In tetrahydrofuran; at 20℃; for 22h; | To a solution of bis(2,6-diisopropylphenyl)carbodiimide (4.35g, 12 mmol) and N,N-diethyl- hydroxylamine (1.6g, 18 mmol) in THF (20 ml) is added finely powdered NaOH (48 mg) and the mixture is stirred at room tempereture for 22 hours. The reaction mixture is then filtered and the filtrate is evaporated on the rotary evaporator below 450C. The residue is recrystal- lized twice from acetonitrile to afford 1.75 g of the title compound as a white solid, mp. 1 13- 1160C.APCI-MS: for C29H45N3O (451.70) found MH+=452.44.1H-NMR (CDCI3, 300 MHz): 7.3-6.8 (m, 6 ArH), 3.6-3.4 (m, 2H, CHMe2), 3.2-3.05 (m, 2H, CHMe2), 3.0-2.8 (m, 4H, 2 x CH2), 1.5-0.9 (3OH, 10 x CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 52℃; for 20h;Inert atmosphere; | To a solution of 4-acetoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine (2.63 g, 12.2 mmol, [prepared as described in Example 1] in tetrahydrofuran (10 ml) is added bis(2,6-diisopropylphe- nyl)carbodiimide (4.52 g, 12.5 mmol) and the solution is heated to 520C under argon for 20 hours. The reaction mixture is evaporated and the residue chromatographed on silica gel with hexane-ethylacetate (5:1 ). The pure fractions are recrystallized from hexane to afford 1.87 g of the compound 10 as colorless crystals, mp. 144-1470C.1H-NMR (CDCI3, 300 MHz): 7.3-6.8 (m, 6 ArH), 5.05-4.96 (m, 1 H, >CH-OAc ), 3.51-3.42 (m, 2H, CHMe2), 3.24-3.17 (m, 2H, CHMe2), 2.01 (s, 3H, OCOCH3), 2.0-1.50 (m, 4H, 2 x CH2), 1.43 (s, 6H, 2 x CH3), 1.25 (d, J=6.9Hz, 24H, 8 x CH3), 1.07 (s, 6H, 2 x CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; | Example 4: 1 ,3-Bis(2,6-diisopropylphenyl)-O-(N-cyclohexylideneamino)-isourea (Cmpd. 4); To a solution of cyclohexanone oxime (1.13 g, 0.01 mol) in dry THF (25 ml) is added finely powdered NaOH (0.04 g) and bis(2,6-diisopropylphenyl)carbodiimide (3.65 g, 0.01 mol). The mixture is then stirred 4 h at room temperature under argon. The turbid mixture is thereafter filtered and evaporated under reduced pressure. The solid residue is crystallized from dichloro- methane-hexane to afford 3.9 g of the title compound as a colorless solid, mp. 150-152 0C.Infusions-MS for C31H45N3O (475.5) found [M+1]+ = 4761H-NMR (CDCI3, 300 MHz): 7.4-6.8 (m, 6H, ArH), 3.6-3.4 (m, 2H), 3.2-3.0 (m, 2H), 2.3-2.1 (m, 4H), 1.8-1.1 (m, 3OH, residual aliphatic H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In tetrahydrofuran; at 20℃; for 20h;Inert atmosphere; | Example 7: 1 ,3-(2,6-Diisopropylphenyl)-O-(N-diphenylmethylideneamino)-isourea (Cmpd. 7); A mixture of benzophenone oxime (1.97 g, lO mmol), bis(2,6-diisopropylphenyl)carbodiimide (3.63 g, 10 mmol) and powdered NaOH (0.04 g) in dry THF (30 ml) is stirred 20 h at room temperature under argon. The mixture is thereafter evaporated and the residue is chromatographed on silica gel (hexanes-ethyl acetate 15:1 ) to afford 1.1 g of the title compound as a colorless glassy solid.ESI-MS for C38H45N3O (559.80) found [M+1]+ = 559.891H-NMR (CDCI3, 300 MHz): 7.5-6.7 (m, 16 ArH), 3.6-3.4 (m, 2H), 3.1-2.9 (m, 2H), 1.5-0.8 (m, 24H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In diethyl ether; hexane; at 0 - 20℃; for 2h; | General procedure: To a suspension of 2-[(dimethylamino)methyl]phenyllithium 1) in Et2O cooled to 0 C, one equivalent of appropriate N,N'-disubstituted carbodiimide (a solution in Et2O) was added. Heterogeneous reaction mixture was allowed to warm to the room temperature and stirred until all the solid particles of 1 disappeared. Colourless solution was filtered and Et2O was evaporated under vacuo to give white solids. Crude products of 2-4 were washed with hexane and dried under vacuo to give pure white crystalline of lithium N,N'-disubstituted [1-(N,N-dimethylaminomethyl)-phen-2-yl]amidinates 2-4. |
Tags: 2162-74-5 synthesis path| 2162-74-5 SDS| 2162-74-5 COA| 2162-74-5 purity| 2162-74-5 application| 2162-74-5 NMR| 2162-74-5 COA| 2162-74-5 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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