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CAS No. : | 900503-08-4 | MDL No. : | MFCD22380007 |
Formula : | C18H30BNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JNHGCLCLMOCPCQ-UHFFFAOYSA-N |
M.W : | 335.25 | Pubchem ID : | 53393373 |
Synonyms : |
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 99.4 |
TPSA : | 48.0 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.93 |
Log Po/w (WLOGP) : | 3.34 |
Log Po/w (MLOGP) : | 2.02 |
Log Po/w (SILICOS-IT) : | 1.27 |
Consensus Log Po/w : | 1.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.5 |
Solubility : | 0.106 mg/ml ; 0.000316 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.6 |
Solubility : | 0.0843 mg/ml ; 0.000251 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.91 |
Solubility : | 0.409 mg/ml ; 0.00122 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 5.74 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
90% | With potassium acetate In 1,4-dioxane at 80℃; for 16 h; Inert atmosphere | A mixture of tert-butyl 3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3- ene-8-carboxylate (Int-le) (10.1 g, 28.4 mmol), bis(pinacolato)diboron (8.7 g, 34.1 mmol), KOAc (8.4 g, 85.3 mmol), PdCl2(dppf)2.CH2Cl2 (1.4g, 1.7mmol), and dppf (1 g, 1.8 mmol) in dioxane (170 ml) was flushed with argon and stirred at 80°C for 16 h. On cooling, the solvent was rotoevaporated, and the crude residue was redissolved in EtOAc (500 ml), washed with water (1 x 125 ml), brine (1 x 125 ml), and dried over gS0 . The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with EtOAc/Hexanes (0-40percent) gave the desired product, tert-butyl 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2~ene-8-carboxylate (8.6 g, 90percent). |
89% | With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 3 h; | tert-Butyl 3-[(trifluoromethane)sulfonyloxy]-8-azabicyclo[3.2. l]oct-2-ene-8- carboxylate (100 mg, 0.28 mmol), 4,4,5, 5-tetramethyl-2-(4,4,5,5-tetramethyl-l, 3,2- dioxaborolan-2-yl)-l,3,2-dioxaborolane (85 mg, 0.36 mmol), 1 , -bis(diphenyl- phosphanyl)ferrocene (5 mg, 0.01 mmol) and potassium acetate (82 mg, 0.84 mmol) were dissolved in 1,4-dioxane (2 mL) and degassed for 5 minutes. Bis[3-(diphenyl- phosphanyl)cyclopenta-2,4-dien-l-yl]iron dichloropalladium dichloromethane complex (7 mg, 0.01 mmol) was added and the mixture was heated at 80°C for a total of 3 h. The reaction mixture was cooled and filtered over celite. The solid was washed with EtOAc (2 x 10 mL) and the combined filtrate was concentrated under vacuum. The crude product was purified using FCC, eluting with a gradient of 0-50percent EtOAc in heptanes, to afford the title compound (86.8 mg, 89percent) as a colourless oil. δH (500 MHz, CDCl3) 6.76 (s, 1H), 4.33 (d, J29.8 Hz, 2H), 2.79 (d, J 17.5 Hz, 1H), 2.12 (dd, J 13.3, 7.3 Hz, 1H), 1.92 (m, 2H), 1.65 (m, 2H), 1.46 (d, J 7.1 Hz, 9H), 1.26 (d, J 6.3 Hz, 12H). |
89% | With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 3 h; Ionic liquid | tert-Butyl 3-[(trifluoromethane)sulfonyloxy]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (100 mg, 0.28 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (85 mg, 0.36 mmol), 1,1′-bis(diphenyl-phosphanyl)ferrocene (5 mg, 0.01 mmol) and potassium acetate (82 mg, 0.84 mmol) were dissolved in 1,4-dioxane (2 mL) and degassed for 5 minutes. Bis[3-(diphenyl-phosphanyl)cyclopenta-2,4-dien-1-yl]iron dichloropalladium dichloromethane complex (7 mg, 0.01 mmol) was added and the mixture was heated at 80° C. for a total of 3 h. The reaction mixture was cooled and filtered over celite. The solid was washed with EtOAc (2×10 mL) and the combined filtrate was concentrated under vacuum. The crude product was purified using FCC, eluting with a gradient of 0-50percent EtOAc in heptanes, to afford the title compound (86.8 mg, 89percent) as a colourless oil. δH (500 MHz, CDCl3) 6.76 (s, 1H), 4.33 (d, J 29.8 Hz, 2H), 2.79 (d, J 17.5 Hz, 1H), 2.12 (dd, J 13.3, 7.3 Hz, 1H), 1.92 (m, 2H), 1.65 (m, 2H), 1.46 (d, J7.1 Hz, 9H), 1.26 (d, J6.3 Hz, 12H). |
79% | With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 16 h; Inert atmosphere | (0521) Tert-butyl 3-(((trifluoromethyl)sulfonyl)oxy)-8-azabicyclo[3.2.1]octan-2-en-8-carboxylate (9.8 g, 27.4 mmol), bis(pinacolato)diboron (10.4 g, 40.9 mmol), potassium acetate (5.4 g, 55 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (1.15 g, 1.4 mmol) and 1,1′-bis(diphenyphosphino)ferrocene (776 mg, 1.4 mmol) were dissolved in 1,4-dioxane (100 mL). Under the protection of nitrogen gas, the reaction was carried out at 80° C. under stirring for 16 h. After the reaction, the mixture was cooled to room temperature, and water (100 mL) was added. The mixture was extracted with ethyl acetate (100 mL×2). The organic phases were combined, dried with anhydrous sodium sulfate, filtrated, and concentrated to get the crude product. The crude product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=20:1) to get the title compound (7.3 g, yield: 79percent). |
76% | With potassium carbonate In 1,4-dioxane at 80℃; for 20 h; | B. A 200 mL round bottom flask was charged with Compound 6b (1.4 g, 3.92 mmol), Pd(dppf)2CI2 (0.09 g, 0.12 mmol), K2CO3 (1.15 g, 11.7 mmol), and <n="188"/>dioxane (23.0 ml_). Bis(pinacolato)diboron (1.1 g, 4.33 mmol) was added and the mixture was heated to 80 0C for 20 h. The mixture was concentrated in-vacuo and purified via flash chromatography (230-400 mesh silica gel 60, DCM) to give 1.0 g (76percent) of Compound 6c as a white solid. 1H NMR (300 MHz, CDCI3) δ 6.76 (d, J = 5.3 Hz, 1 H), 4.27-4.35 (m, 2 H), 2.80-2.90 (m, 1 H), 2.03-2.12 (m, 1 H), 1.88-1.94 (m, 4 H), 1.44 (s, 9 H), and 1.26 (s, 12 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With (diphenylphosphin)ferrocene In 1,4-dioxane at 85℃; for 1 h; | b) The suspension of compound 47 (1.9 g, 3.75 mmol), compound 48 (948 mg, 3.75 mmol, Carbocore), PdCl2(dppf)CH2Cl2 (86 mg, 0.11 mmol, Aldrich), diphenylphosphinoferracene (61 mg, 0.11 mmol, Aldrich) and KOAc (1.03 g, 10.5 mmol) in 1,4-dioxane (15 ml) was heated at 85° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with EtOAc (100 ml) and washed with brine. The aqueous phase was further extracted with EtOAc (2.x.100 ml) and the combined organic phase was dried with Na2SO4, filtered and concentrated to dryness. The residue was purified on CombiFlash.(R). with 10-20percent EtOAc in hexane to obtain compound 49 (688 mg, yield 55percent). |
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