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[ CAS No. 287944-10-9 ]

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Chemical Structure| 287944-10-9
Chemical Structure| 287944-10-9
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CAS No. :287944-10-9 MDL No. :MFCD08669391
Formula : C11H19BO2 Boiling Point : 210°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :194.08 g/mol Pubchem ID :15486611
Synonyms :

Safety of [ 287944-10-9 ]

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 [ 287944-10-9 ]

  • Upstream synthesis route of [ 287944-10-9 ]
  • Downstream synthetic route of [ 287944-10-9 ]

[ 287944-10-9 ] Synthesis Path-Upstream   1~11

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YieldReaction ConditionsOperation in experiment
99% With potassium acetate In 1,4-dioxane at 110℃; for 3 h; Inert atmosphere Example XIV2-Cyclopent-1 -enyl-4,4,5,5-tetramethyl-[1 ,3,21dioxaborolane Under argon 4,31 g 1 -chlor-1 -cyclopenten and 12,5 g bis-(pinacolato)-diboron are dissolved 160 ml 1 ,4-dioxane, mixed with 8 g potassium acetate and purged for 5 minutes with argon. 370 mg Tris-(dibenzylidenaceton)-dipalladium-(0) ([Pd2dba3] and 780 mg 2- cyclohexylphosphino-2',4',6'-triisopropyl-1 ,1 '-biphenyl are added and the mixture is heated for 3 hours to 1 10°C. After cooling to room temperature it is diluted with diethylether and washed with water and brine. The organic phase is dried with magnesium sulphate and the solvents are evaporated in vacuo. The residue is triturated with petrole ether. After removing the precipitate by filtration the solvent of the mother liquor is evaporated in vacuo.Yield: 13,1 g (99 percent of theory)Mass spectrometry (El): m/z = 194 [M]+
99% With potassium acetate In 1,4-dioxane at 110℃; for 3 h; Inert atmosphere Under argon 4.31 g 1-chlor-1-cyclopenten and 12.5 g bis-(pinacolato)-diboron are dissolved 160 ml 1,4-dioxane, mixed with 8 g potassium acetate and purged for 5 minutes with argon. 370 mg Tris-(dibenzylidenaceton)-dipalladium-(0) ([Pd2 dba3] and 780 mg 2-cyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl are added and the mixture is heated for 3 hours to 110° C. After cooling to room temperature it is diluted with diethylether and washed with water and brine. The organic phase is dried with magnesium sulphate and the solvents are evaporated in vacuo. The residue is triturated with petrole ether. After removing the precipitate by filtration the solvent of the mother liquor is evaporated in vacuo.Yield: 13.1 g (99percent of theory)Mass spectrometry (EI): m/z=194 [M]+
99% With 2-cyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl; potassium acetate In 1,4-dioxane at 110℃; for 3 h; Inert atmosphere Example XIV 2-Cvclopent-1-enyl-4,4,5,5-tetramethyl-[1 ,3,21dioxaborolane Under argon 4,31 g 1-chlor-1-cyclopenten and 12,5 g bis-(pinacolato)-diboron are dissolved 160 ml 1 ,4-dioxane, mixed with 8 g potassium acetate and purged for 5 minutes with argon. 370 mg Tris-(dibenzylidenaceton)-dipalladium-(0) ([Pd2dba3] and 780 mg 2- cyclohexylphosphino-2',4',6'-triisopropyl-1 ,1 '-biphenyl are added and the mixture is heated for 3 hours to 110°C. After cooling to room temperature it is diluted with diethylether and washed with water and brine. The organic phase is dried with magnesium sulphate and the solvents are evaporated in vacuo. The residue is triturated with petrole ether. After removing the precipitate by filtration the solvent of the mother liquor is evaporated in vacuo.Yield: 13, 1 g (99 percent of theory)Mass spectrometry (El): m/z = 194 [M]+
99% With tris-(dibenzylideneacetone)dipalladium(0); 2-cyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl; potassium acetate In 1,4-dioxane at 110℃; for 3 h; Inert atmosphere Under argon 4.31 g 1-chlor-1-cyclopenten and 12.5 g bis-(pinacolato)-diboron are dissolved 160 ml 1,4-dioxane, mixed with 8 g potassium acetate and purged for 5 minutes with argon. 370 mg Tris-(dibenzylidenaceton)-dipalladium-(0) ([Pd2dba3] and 780 mg 2-cyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl are added and the mixture is heated for 3 hours to 110° C. After cooling to room temperature it is diluted with diethylether and washed with water and brine. The organic phase is dried with magnesium sulphate and the solvents are evaporated in vacuo. The residue is triturated with petrole ether. After removing the precipitate by filtration the solvent of the mother liquor is evaporated in vacuo.Yield: 13.1 g (99percent of theory)Mass spectrometry (EI): m/z=194 [M]+

Reference: [1] Patent: WO2011/101424, 2011, A1, . Location in patent: Page/Page column 230-231
[2] Patent: US2012/46304, 2012, A1, . Location in patent: Page/Page column 123
[3] Patent: WO2012/110599, 2012, A1, . Location in patent: Page/Page column 230-231
[4] Patent: US2013/53404, 2013, A1, . Location in patent: Paragraph 1781; 1782; 1783
[5] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3543 - 3548
[6] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5359 - 5363
  • 2
  • [ 61676-62-8 ]
  • [ 17529-98-5 ]
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 26, p. 8481 - 8490
[2] Synthetic Communications, 2008, vol. 38, # 22, p. 3984 - 3995
  • 3
  • [ 28075-49-2 ]
  • [ 73183-34-3 ]
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Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 27, p. 8001 - 8006
[2] Journal of the American Chemical Society, 2002, vol. 124, # 27, p. 8001 - 8006
  • 4
  • [ 930-29-0 ]
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Reference: [1] Patent: WO2012/148511, 2012, A1, . Location in patent: Page/Page column 62-63
  • 5
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YieldReaction ConditionsOperation in experiment
0.9 g
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 20℃; for 2.75 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 4 h; Inert atmosphere
2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was synthesized in a similar procedure to the published Shapiro protocol.22 In a 250 mL round bottom flask equipped with a condenser, p-tolylsulfonylhydrazine (18.0 g, 96.0 mmol, 1.0equiv) was dissolved in 100percent EtOH (20 mL). Cyclopentanone (8.6 mL, 8.1 g, 96 mmol, 1.0 equiv) was added and the reaction heated to reflux at 100 °C. After 5 min the suspension dissolved, and after another 15 min, a white solid appeared. After refluxing for 1.5 h the reaction flask was cooled to 0 °C and the resulting solid was then collected by filtration and washed with ice-cold EtOH. After drying under reduced pressure, the hydrazone was isolated as a white powder in a quantitative yield. The cyclopentanone p-tolylsulfonylhydrazine (1.62 g, 5.40 mmol, 1.00 equiv) and 20 mL dry hexane was added to a flame dried 250 mL round bottom flask equipped with a septum and magnetic stirbar. To this mixture anhydrous TMEDA (20 mL) was added and the reaction cooled to –78 °C, where it was maintained for15 min, after which 2.5 M n-BuLi (10 mL, 25 mmol, 4.6 equiv) was added. The reaction mixture was then stirred at –78 °C for 1 h and then warmed to room temperature and stirred for 1.5 h at this temperature during this time N2 gas was extruded from the reaction and after the allotted time the reaction was cooled backdown to –78 °C and maintained for 15 min, after which pinacol isopropyl borate (5.5 mL, 4.5 g, 24 mmol, 4.4 equiv) was added. The reaction mixture was stirred at –78°C for 1 h, and then the dry ice bath was removed and the mixture was stirred at room temperature for 3 h, before being quenched via the addition of 10percent HCl (50 mL) and extracted with Et2O (4 × 50 mL), (10percent HCl was used instead of saturated NH4Cl, to increase the acidity on work–up. By increasing the acidity, this reduced the amount of an emulsion and allowed for easier work-up). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified via column chromatography (95:5 hexanes/EtOAc) to give the desired compound (0.90 g, 86percent) as a faint yellow oil. Spectral and analytical properties of this compound were in accordance with the literature.22
Reference: [1] Tetrahedron, 2014, vol. 70, # 3, p. 678 - 683
  • 6
  • [ 142-29-0 ]
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Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7715 - 7723
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4051 - 4053
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4051 - 4053
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4051 - 4053
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4051 - 4053
  • 7
  • [ 930-29-0 ]
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5589 - 5591
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Reference: [1] Synthesis, 2000, # 6, p. 778 - 780
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Reference: [1] Synthesis, 2000, # 6, p. 778 - 780
  • 10
  • [ 142-29-0 ]
  • [ 73183-34-3 ]
  • [ 66217-55-8 ]
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Reference: [1] Chemical Communications, 2010, vol. 46, # 6, p. 907 - 909
[2] Chemical Communications, 2010, vol. 46, # 6, p. 907 - 909
  • 11
  • [ 120-92-3 ]
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Reference: [1] Tetrahedron, 2014, vol. 70, # 3, p. 678 - 683
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