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英语翻译
1,3,5-Tris((3-(4-pyridyl)ethynyl)bicyclo[1.1.1]pent-1-ylethynyl)
benzene (5).In a two-neck flask,23 (200 mg,1.037
mmol) and 1,3,5-triiodobenzene (150 mg,0.33 mmol) were
combined,evacuated,and placed under argon.Freshly distilled
dry piperidine (20 mL) was added from a syringe,and the
mixture was stirred at room temperature until the solid was
dissolved.Then,the solution was degassed by three freezepump-
thaw cycles.After warming to room temperature,Pd-(PPh3)4 (20 mg,5 mol %) was added from a tip tube,and the
reaction mixture was stirred at 55 °C for 18 h.Aqueous NaOH
(4 M,2.5 mL) was added,and the solution was stirred for 15
min before the solvents were evaporated under reduced
pressure.The crude solid was dissolved in chloroform and
washed with aqueous EDTA solution (1 M,3 \2 5 mL).Then,
the organic layer was extracted with HCl (2 M,5 \2 5 mL).
The aqueous layer was basified with NaOH (2 M,30 mL) and
extracted with chloroform (4 \2 10 mL).After drying over
Na2SO4,the organic solvent was evaporated under reduced
pressure,and the crude product was purified by PTLC
(alumina/hexane-ethyl acetate,5:1) to yield 5 as a white
solid:116 mg (54%); mp 178 °C (dec); 1H NMR (CDCl3,300
MHz) ä 2.44 (s,18 H),7.22 (dd,J ) 4.3 Hz,J ) 1.4 Hz,6 H),
7.35 (s,3 H),8.52 (dd,J ) 4.3 Hz,J ) 1.4 Hz,6 H); 13C {1H}
NMR (CDCl3,124 MHz) ä 30.55,30.87,58.88,77.77,78.72,
88.99,99.92,123.37,125.76,131.14,134.37,149.67; IR (KBr)
549,571,596,682,800,819,877,989,1081,1216,1281,1384,
1405,1489,1539,1593,2227,2877,2914,2968,2987 cm-1;
MS (EI+) m/z (rel int) 651 ([M]+,6),650 ([M - H]+,4),537
(100),459 (35),443 (17),412 (14),378 (5),315 (15),287 (8),
264 (5),228 (7),167 (5),142 (9),128 (27),84 (11),55 (23);
HRMS calcd 651.2674,found 651.2681.Anal.Calcd for
C48H33N3:C,88.45; H,5.10; N,6.45.Found:C,88.43; H,4.90;
N,6.58
1,3,5-Tris((3-(4-pyridyl)ethynyl)bicyclo[1.1.1]pent-1-ylethynyl)
benzene (5).In a two-neck flask,23 (200 mg,1.037
mmol) and 1,3,5-triiodobenzene (150 mg,0.33 mmol) were
combined,evacuated,and placed under argon.Freshly distilled
dry piperidine (20 mL) was added from a syringe,and the
mixture was stirred at room temperature until the solid was
dissolved.Then,the solution was degassed by three freezepump-
thaw cycles.After warming to room temperature,Pd-(PPh3)4 (20 mg,5 mol %) was added from a tip tube,and the
reaction mixture was stirred at 55 °C for 18 h.Aqueous NaOH
(4 M,2.5 mL) was added,and the solution was stirred for 15
min before the solvents were evaporated under reduced
pressure.The crude solid was dissolved in chloroform and
washed with aqueous EDTA solution (1 M,3 \2 5 mL).Then,
the organic layer was extracted with HCl (2 M,5 \2 5 mL).
The aqueous layer was basified with NaOH (2 M,30 mL) and
extracted with chloroform (4 \2 10 mL).After drying over
Na2SO4,the organic solvent was evaporated under reduced
pressure,and the crude product was purified by PTLC
(alumina/hexane-ethyl acetate,5:1) to yield 5 as a white
solid:116 mg (54%); mp 178 °C (dec); 1H NMR (CDCl3,300
MHz) ä 2.44 (s,18 H),7.22 (dd,J ) 4.3 Hz,J ) 1.4 Hz,6 H),
7.35 (s,3 H),8.52 (dd,J ) 4.3 Hz,J ) 1.4 Hz,6 H); 13C {1H}
NMR (CDCl3,124 MHz) ä 30.55,30.87,58.88,77.77,78.72,
88.99,99.92,123.37,125.76,131.14,134.37,149.67; IR (KBr)
549,571,596,682,800,819,877,989,1081,1216,1281,1384,
1405,1489,1539,1593,2227,2877,2914,2968,2987 cm-1;
MS (EI+) m/z (rel int) 651 ([M]+,6),650 ([M - H]+,4),537
(100),459 (35),443 (17),412 (14),378 (5),315 (15),287 (8),
264 (5),228 (7),167 (5),142 (9),128 (27),84 (11),55 (23);
HRMS calcd 651.2674,found 651.2681.Anal.Calcd for
C48H33N3:C,88.45; H,5.10; N,6.45.Found:C,88.43; H,4.90;
N,6.58
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