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CAS No. : | 124276-57-9 | MDL No. : | MFCD09743443 |
Formula : | C10H7Cl2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SJDZLTHRJVBKJM-UHFFFAOYSA-N |
M.W : | 212.08 | Pubchem ID : | 11600939 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.37 |
TPSA : | 23.79 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.04 cm/s |
Log Po/w (iLOGP) : | 2.38 |
Log Po/w (XLOGP3) : | 3.59 |
Log Po/w (WLOGP) : | 3.49 |
Log Po/w (MLOGP) : | 3.12 |
Log Po/w (SILICOS-IT) : | 4.09 |
Consensus Log Po/w : | 3.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.69 |
Solubility : | 0.0431 mg/ml ; 0.000203 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.78 |
Solubility : | 0.0355 mg/ml ; 0.000167 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.54 |
Solubility : | 0.0061 mg/ml ; 0.0000288 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.51 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 sodium hydroxide In methanol for 12h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium hydroxide In ethylene glycol for 10h; Heating; | |
With hydrogenchloride at 100℃; for 12h; | ||
With lithium hydroxide In water for 18h; Reflux; |
With lithium hydroxide In water; ethylene glycol at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 55 - 75℃; for 2h; | |
Stage #1: 3,4-dichloro-benzeneacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: ethylene dibromide In N,N-dimethyl-formamide for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium carbonate at 145 - 150℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: SOCl2 / benzene / 8 h / Heating | ||
Multi-step reaction with 2 steps 1: aq. conc. HCl / 12 h / 100 °C 2: SOCl2 / CH2Cl2 / 6 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: triethylamine / acetone / 2.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: SOCl2 / benzene / 8 h / Heating 3: NaHCO3 / H2O; acetone / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: SOCl2 / benzene / 8 h / Heating 3: NaHCO3 / H2O; acetone / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: SOCl2 / benzene / 8 h / Heating 3: NaHCO3 / H2O; acetone / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: triethylamine / acetone / 2.5 h / 0 - 20 °C 3: NaHCO3 / acetone / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: triethylamine / acetone / 2.5 h / 0 - 20 °C 3: NaHCO3 / acetone / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH / ethane-1,2-diol / 10 h / Heating 2: triethylamine / acetone / 2.5 h / 0 - 20 °C 3: NaHCO3 / acetone / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K-t-butoxide / dimethylformamide / 24 h / Ambient temperature 2: aq. NaOH / methanol / 12 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aq. conc. HCl / 12 h / 100 °C 2: SOCl2 / CH2Cl2 / 6 h 3: Et3N / CH2Cl2 / 2 h / 1.) 0 deg C, 2.) RT, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NaNH2 / diethyl ether 2: K-t-butoxide / dimethylformamide / 24 h / Ambient temperature 3: aq. NaOH / methanol / 12 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-hexyllithium / tetrahydrofuran; hexane / 0.17 h / -75 °C 1.2: 0.25 h 1.3: 0.25 h / 50 °C 2.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran / 2 h / 5 °C | ||
Multi-step reaction with 2 steps 1.1: n-hexyllithium / tetrahydrofuran; hexane / 0.17 h / -75 °C 1.2: 0.25 h 1.3: 0.25 h / 50 °C 2.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / 2 h / 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: 2-bromo-pyridine With n-hexyllithium In tetrahydrofuran; hexane at -75℃; for 0.166667h; Stage #2: 1-(3,4-dichlorophenyl)cyclopropanecarbonitrile In tetrahydrofuran; hexane for 0.25h; Stage #3: With sulfuric acid at 50℃; for 0.25h; | 231A Example 231A Example 231A [1-(3,4-dichlorophenyl)cyclopropyl](pyridin-2-yl)methanone A solution of 2-bromopyridine (0.688 mL, 7.07 mmol) in THF (10 mL) was cooled to -75° C. 2.3M n-Hexyllithium (3.08 mL, 7.07 mmol) in hexane was added dropwise at -75° C. After 10 minutes, 1-(3,4-dichlorophenyl)cyclopropanecarbonitrile (1.00 g, 4.72 mmol) was added. After 15 minutes, 2N sulfuric acid (10 mL) was added and the mixture was heated at 50° C. for 15 minutes. The mixture was cooled to ambient temperature, diluted with MTBE and water, and partitioned. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel and eluted with 0-20% EtOAc in hexanes to give Example 231A (1.27 g, 92% yield). MS (DCIf): m/z 290.2 (M+H). 1H NMR (300 MHz, DMSO-d6) δ 8.46 (ddd, J=4.7, 1.7, 1.0 Hz, 1H), 7.91 (td, J=7.7, 1.7 Hz, 1H), 7.82-7.76 (m, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.50-7.42 (m, 2H), 7.22 (dd, J=8.4, 2.1 Hz, 1H), 1.75 (q, J=4.2 Hz, 2H), 1.45 (q, J=4.3 Hz, 2H). |
92% | Stage #1: 2-bromo-pyridine With n-hexyllithium In tetrahydrofuran; hexane at -75℃; for 0.166667h; Stage #2: 1-(3,4-dichlorophenyl)cyclopropanecarbonitrile In tetrahydrofuran; hexane for 0.25h; Stage #3: With sulfuric acid In tetrahydrofuran; hexane at 50℃; for 0.25h; | 231A [ 1 -(3 ,4-dichlorophenyl)cyclopropyl](pyridin-2-yl)methanone [ 1 -(3 ,4-dichlorophenyl)cyclopropyl](pyridin-2-yl)methanone[520] A solution of 2-bromopyridine (0.688 mL, 7.07 mmol) in THF (10 mL) was cooled to -75°C. 2.3M n-Hexyllithium (3.08 mL, 7.07 mmol) in hexane was added dropwise at -75°C. After 10 minutes, l-(3,4-dichlorophenyl)cyclopropanecarbonitrile (1.00 g, 4.72 mmol) was added. After 15 minutes, 2N sulfuric acid (10 mL) was added and the mixture was heated at 50 °C for 15 minutes. The mixture was cooled to ambient temperature, diluted with MTBE and water, and partitioned. The organic layer was washed with brine, dried over Na2S04, filtered, and concentrated. The residue waschromatographed on silica gel and eluted with 0-20 % EtOAc in hexanes to give Example 231 A (1.27 g, 92% yield). MS (DCI+): m/z 290.2 (M+H). ? NMR (300 MHz, DMSO-d6) ? 8.46 (ddd, J= 4.7, 1.7, 1.0 Hz, 1H), 7.91 (td, J= 7.7, 1.7 Hz, 1H), 7.82 - 7.76 (m, 1H), 7.52 (d, J= 2.1 Hz, 1H), 7.50 - 7.42 (m, 2H), 7.22 (dd, J= 8.4, 2.1 Hz, 1H), 1.75 (q, J = 4.2 Hz, 2H), 1.45 (q, J= 4.3 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: lithium hydroxide / water / 18 h / Reflux 2.1: sulfuric acid / 18 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 4.1: triethylamine / dichloromethane / 2 h / 0 °C 5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 5.2: 72 h / 0 - 25 °C 6.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 6.2: 12 h 7.1: triphenylphosphine sulfide; water; N-Bromosuccinimide / dichloromethane / 24 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium hydroxide / water / 18 h / Reflux 2: sulfuric acid / 18 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium hydroxide / water / 18 h / Reflux 2: sulfuric acid / 18 h / Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide / water / 18 h / Reflux 2: sulfuric acid / 18 h / Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 4: triethylamine / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: lithium hydroxide / water / 18 h / Reflux 2.1: sulfuric acid / 18 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 4.1: triethylamine / dichloromethane / 2 h / 0 °C 5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 5.2: 72 h / 0 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: lithium hydroxide / water / 18 h / Reflux 2.1: sulfuric acid / 18 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 4.1: triethylamine / dichloromethane / 2 h / 0 °C 5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 5.2: 72 h / 0 - 25 °C 6.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C 6.2: 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium hydroxide / water; ethylene glycol / 24 h / 100 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C 3: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H56BN3Si / tetrahydrofuran / 36 h / 60 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium hydroxide / water; ethylene glycol / 24 h / 100 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃; for 12h; |
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