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[ CAS No. 287944-06-3 ]

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Chemical Structure| 287944-06-3
Chemical Structure| 287944-06-3
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Product Details of [ 287944-06-3 ]

CAS No. :287944-06-3 MDL No. :MFCD11520535
Formula : C16H29BO2 Boiling Point : 290.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :264.21 g/mol Pubchem ID :-
Synonyms :

Safety of [ 287944-06-3 ]

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:

Application In Synthesis of [ 287944-06-3 ]

  • Downstream synthetic route of [ 287944-06-3 ]

[ 287944-06-3 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 352-34-1 ]
  • [ 287944-06-3 ]
  • 4-(tert-Butyl)-1-(4-fluorophenyl)cyclohexene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide In water at 80℃; for 16h;
  • 2
  • [ 77412-96-5 ]
  • [ 25015-63-8 ]
  • [ 2228-98-0 ]
  • 2-(4-<i>tert</i>-butyl-cyclohex-2-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
  • [ 287944-06-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In 1,4-dioxane at 80℃; for 16h; Title compound not separated from byproducts;
  • 3
  • [ 28075-49-2 ]
  • [ 287944-06-3 ]
  • 4-tert-butyl-1-(1-cyclopentenyl)-1-cyclohexene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate In N,N-dimethyl-formamide at 80℃; for 16h;
  • 4
  • [ 77412-96-5 ]
  • [ 73183-34-3 ]
  • [ 287944-06-3 ]
YieldReaction ConditionsOperation in experiment
94% With triphenylphosphine In toluene mixt. in toluene stirred at 50°C for 3 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.);
94 % Chromat. With potassium phenolate; triphenylphosphine In toluene at 50℃; for 3h;
With potassium acetate In 1,4-dioxane at 80℃; for 18h; 8.b; 9.b (b) 2-(4-tert-Butyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. To a solution of trifluoro-methanesulfonic acid 4-tert-butyl-cyclohex-1-enyl ester, Example 8(a), (5.6 g, 21.2 mmol) in dioxane (100 mL) was added bis(pinacolato)diboron (5.6 g, 22 mmol, Aldrich), potassium acetate (6 g, 61 mmol), PdCl2(dppf) (315 mg, 0.6 mmol, Strem) and dppf (332 mg, 0.6 mmol, Strem) under nitrogen atmosphere. The reaction mixture was heated at 80° C. with stirring for 18 h, allowed to cool to room temperature, and filtered through Celite. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to give the title compound as a white amorphous solid. MS (ESI, pos. ion.) m/z: 265 (M+1).
With potassium acetate In 1,4-dioxane at 80℃; for 16h; 7.7d To trifluoromethanesulfonic acid 4-t-butylcyclohex-1-enyl ester (55.0 g, 192.1 mmol) prepared in Example (2a) were added bis(pinacolato)diboron (56.1 g, 220.9 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium(II) dichloromethane complex (4.88 g, 5.98 mmol), potassium acetate (56.6 g, 576.3 mmol) and dioxane (400 mL), and the mixture was stirred at an external temperature of 80° C. for 16 hours. After the reaction, the reaction mixture was air-cooled to room temperature, ethyl acetate and water were added to the reaction mixture, and the organic layer was separated off. The obtained organic layer was again washed with water, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 38.97 g of the title compound as a light yellow solid, in racemic form at the position of t-butyl. 1H-NMR (400 MHz, CDCl3) δ: 0.85 (s, 9H), 1.00-1.43 (m, 14H), 1.78-1.90 (m, 2H), 1.98-2.17 (m, 2H), 2.24-2.32 (m, 1H), 6.59 (dd, J=2.0 Hz, 1H).

  • 5
  • [ 862461-94-7 ]
  • [ 287944-06-3 ]
  • 4-[6-(4-tert-butyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine [ No CAS ]
  • N-{4-[6-(4-tert-butyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 120℃; for 0.25h; 8.f; 9.f (f) N-{4-[6-(4-tert-Butyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide and 4-[6-(4-tert-butyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine. A mixture of N-[4-(6-iodo-pyrimidin-4-yloxy)-benzothiazol-2-yl]-acetamide. Example 8(e), (100 mg, 0.24 mmol), 2-(4-tert-butyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, Example 8(b), (96 mg, 0.36 mmol), PdCl2(PPh3)2 (17 mg, 0.02 mmol), and Na2CO3 (38 mg, 0.36 mmol) in DME/EtOH/H2O (2:1:2, 2.0 mL) was heated in a microwave at 120° C. with stirring for 15 min. The reaction mixture was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography with eluent MeOH/CH2Cl2 (1:80) and with eluent MeOH/CH2Cl2 (1:50) to give N-{4-[6-(4-tert-butyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide [M.p.: >200° C. (dec.); MS (ESI, pos. ion.) m/z: 423 (M+1)] and 4-[6-(4-tert-butyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine [M.p.: 208.3-208.8° C.; MS (ESI, pos. ion.) m/z: 381 (M+1)].
  • 6
  • [ 5344-78-5 ]
  • [ 287944-06-3 ]
  • [ 859220-08-9 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate In 1,2-dimethoxyethane; water at 20 - 70℃; for 18.5h; 12.12a A mixture of 2-(4-t-butylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.17 g, 12 mmol) prepared in Example (7d), 1-bromo-4-methoxy-2-nitrobenzene (2.32 g, 10 mmol), tripotassium phosphate(4.8 g, 15 mmol), 1,2-dimethoxyethane (30 mL) and water (5 mL) was stirred at room temperature under a nitrogen atmosphere. To this reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (578 mg, 0.5 mmol). The mixture was stirred at an external temperature of 70° C. for 18 hours and 30 minutes. Ethyl acetate and water were added to the reaction mixture, which was then passed through Celite for filtration. The filtrate was subjected to oil-water distribution and the obtained organic layer was dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 2.89 g of the title compound as a yellow solid, in racemic form at the position of t-butyl. 1H-NMR (400 MHz, CDCl3) δ: 0.89 (s, 9H), 1.31-1.43 (m, 2H), 1.86-1.95 (m, 2H), 2.13-2.34 (m, 3H), 3.85 (s, 3H), 5.59-5.61 (m, 1H), 7.05 (dd, J=8.8, 2.4 Hz, 1H), 7.17 (d, J=8.8 Hz, 1H), 7.31 (d, J=2.4 Hz, 1H).
  • 7
  • [ 859217-97-3 ]
  • [ 287944-06-3 ]
  • [ 859217-98-4 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate In 1,2-dimethoxyethane at 90℃; for 2.5h; 7.7e To a solution of trifluoromethanesulfonic acid 5-(4-methoxypiperidin-1-yl)-2-nitrophenyl ester (3.276 g, 8.52 mmol) prepared in Example (7c) in 1,2-dimethoxyethane (80 mL) were added 2-(4-t-butylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.478 g, 9.38 mmol) prepared in Example (7d), tetrakis(triphenylphosphine)palladium(0) (492 mg, 0.426 mmol) and tripotassium phosphate (2.714 g, 12.79 mmol), and the mixture was stirred at an external temperature of 90° C. for 2 hours and 30 minutes under a nitrogen atmosphere. After the reaction, brine and ethyl acetate were added to the reaction mixture. The organic layer was separated off and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1.87 g of the title compound as orange crystals, in racemic form at the position of t-butyl. 1H-NMR (400 MHz, CDCl3) δ: 0.90 (s, 9H), 1.38-1.43 (m, 2H), 1.64-1.74 (m, 2H), 1.86-2.00(m, 3H), 2.13-2.33 (m, 4H), 3.21 (ddd, J=12.4, 8.4, 3.6 Hz, 2H), 3.38 (s, 3H), 3.46 (m, 1H), 3.67 (ddd, J=11.2, 7.2, 3.6 Hz, 2H), 5.57(t, J=2.4 Hz, 1H), 6.54 (d, J=2.8 Hz, 1H), 6.72 (dd, J=9.6, 2.8 Hz, 1H), 8.07 (d, J=9.6 Hz, 1H).
  • 8
  • [ 61676-62-8 ]
  • [ 41780-53-4 ]
  • [ 287944-06-3 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 4-tert-butylcyclohexanone tosylhydrazone With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 20℃; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexane at -78 - 20℃; for 4h; Inert atmosphere;
75% Stage #1: 4-tert-butylcyclohexanone tosylhydrazone With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 20℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexane at -78 - 20℃;
Stage #1: 4-tert-butylcyclohexanone tosylhydrazone With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 25℃; for 3h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexane at -78℃;
  • 9
  • [ 181658-26-4 ]
  • [ 287944-06-3 ]
  • [ 1041002-99-6 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; palladium diacetate; triphenylphosphine In water at 111℃; for 48h;
  • 10
  • [ 287944-06-3 ]
  • C18H21NO3 [ No CAS ]
  • C18H21NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium periodate; ammonium acetate / water; acetone / 48 h 2: pyridine; copper diacetate; sodium sulfate / 1,2-dichloro-ethane / 12 h / 25 °C 3: benzene-d6 / 16 h / 80 °C
  • 11
  • [ 287944-06-3 ]
  • [ 850567-91-8 ]
YieldReaction ConditionsOperation in experiment
With sodium periodate; ammonium acetate In water; acetone for 48h;
With sodium periodate; ammonium acetate; water In acetone
  • 12
  • [ 287944-06-3 ]
  • [ 1402704-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium periodate; ammonium acetate / water; acetone / 48 h 2: pyridine; copper diacetate; sodium sulfate / 1,2-dichloro-ethane / 12 h / 25 °C
  • 13
  • [ 287944-06-3 ]
  • C17H21N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; sodium periodate; ammonium acetate / acetone 2: copper diacetate; pyridine; sodium sulfate / acetonitrile / 20 °C / Green chemistry
  • 14
  • [ 287944-06-3 ]
  • 4-(tert-butyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: water; sodium periodate; ammonium acetate / acetone 2: copper diacetate; pyridine; sodium sulfate / acetonitrile / 20 °C / Green chemistry 3: acetic acid; oxygen / acetonitrile / 80 °C / Green chemistry
  • 15
  • [ 98-53-3 ]
  • [ 287944-06-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol / 2 h / 70 °C / Reflux 2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane / 3 h / -78 - 25 °C 2.2: -78 °C
Multi-step reaction with 2 steps 1.1: 2-chloropyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: Chromium (III) chloride; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium / tetrahydrofuran / 18 h / 40 °C / Schlenk technique; Inert atmosphere
  • 16
  • tert-butyl 3-methyl-6-(((trifluoromethyl)sulfonyl)oxy)-3,4-dihydropyridine-1(2H)-carboxylate [ No CAS ]
  • [ 287944-06-3 ]
  • tert-butyl 6-(4-tert-butylcyclohexen-1-yl)-3-methyl-3,4-dihydro-2H-pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.12% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; water monomer at 80℃; for 14h; Inert atmosphere; 4Z.1 Step 1: Synthesis of tert-butyl 6-(4-tert-butylcyclohexen-1-yl)-3-methyl-3,4-dihydro-2H-pyridine- 1-carboxylate A stirring solution of tert-butyl 3-methyl-6-(trifluoromethylsulfonyloxy)-3,4-dihydro- 2H-pyridine-1-carboxylate (7.19 g, 20.82 mmol), 2-(4-tert-butylcyclohexen-1-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (5 g, 18.92 mmol)) and Sodium carbonate (6.02 g, 56.77 mmol) in 1,4-Dioxane (90 mL) and Water (30 mL) was purged with argon. Then, Pd(dppf)Cl2 (772.71 mg, 946.22 μmol) was added under argon. The reaction mixture was stirred under argon at 80 °C for 14 hours After 14 hours, the reaction mixture was cooled and filtered. The filter cake was washed with 1.4-dioxane (2 x 20 mL) and discarded. The filtrate was evaporated in vacuo and the residue was purified by column chromatography to afford tert-butyl 6-(4-tert- butylcyclohexen-1-yl)-3-methyl-3,4-dihydro-2H-pyridine-1-carboxylate (3.10 g, 9.30 mmol, 49.12% yield) as colorless oil. LCMS(ESI): [M+Boc]+ m/z: calcd 333.3; found 278.2 (t-Bu cleaved product mass); Rt = 1.903 min
49.12% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; water monomer at 80℃; for 14h; Inert atmosphere; 4Z.1 Step 1: Synthesis of tert-butyl 6-(4-tert-butylcyclohexen-1-yl)-3-methyl-3,4-dihydro-2H-pyridine- 1-carboxylate A stirring solution of tert-butyl 3-methyl-6-(trifluoromethylsulfonyloxy)-3,4-dihydro- 2H-pyridine-1-carboxylate (7.19 g, 20.82 mmol), 2-(4-tert-butylcyclohexen-1-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (5 g, 18.92 mmol)) and Sodium carbonate (6.02 g, 56.77 mmol) in 1,4-Dioxane (90 mL) and Water (30 mL) was purged with argon. Then, Pd(dppf)Cl2 (772.71 mg, 946.22 μmol) was added under argon. The reaction mixture was stirred under argon at 80 °C for 14 hours After 14 hours, the reaction mixture was cooled and filtered. The filter cake was washed with 1.4-dioxane (2 x 20 mL) and discarded. The filtrate was evaporated in vacuo and the residue was purified by column chromatography to afford tert-butyl 6-(4-tert- butylcyclohexen-1-yl)-3-methyl-3,4-dihydro-2H-pyridine-1-carboxylate (3.10 g, 9.30 mmol, 49.12% yield) as colorless oil. LCMS(ESI): [M+Boc]+ m/z: calcd 333.3; found 278.2 (t-Bu cleaved product mass); Rt = 1.903 min
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