(Z)-icos-11-en-1-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure for compound 7, 11-eicosenol (1.1 g, 3.7 mmol) and THF (3 mL) were reacted with 1 (0.047 g, 2 mol %) and 1-butene to provide 9 (0.37 g, 47% yield, 76% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.45 (2H, m), 3.63 (2H, t, J=6.6 Hz), 1.94-2.06 (4H, m), 1.56 (2H, dt, J=13.5, 6.7 Hz), 1.27, (15H, m), 0.96 (3H, m); 13C NMR (CDCl3): δ 131.7, 129.5, 63.2, 33.0, 29.9, 29.7, 29.7, 29.7, 29.6, 29.4, 27.2, 25.9, 20.7, 14.6; HRMS (FAB): 212.2135, [C14H28O]+ requires 212.2140. to provide 9 (0.37 g, 47% yield, 76% Z as determined by 13C-NMR) as a colorless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure for compound 7, 11-eicosenol (1.1 g, 3.7 mmol) and THF (3 mL) were reacted with 1 (0.047 g, 2 mol %) and 1-butene to provide 9 (0.37 g, 47% yield, 76% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.45 (2H, m), 3.63 (2H, t, J=6.6 Hz), 1.94-2.06 (4H, m), 1.56 (2H, dt, J=13.5, 6.7 Hz), 1.27, (15H, m), 0.96 (3H, m); 13C NMR (CDCl3): δ 131.7, 129.5, 63.2, 33.0, 29.9, 29.7, 29.7, 29.7, 29.6, 29.4, 27.2, 25.9, 20.7, 14.6; HRMS (FAB): 212.2135, [C14H28O]+ requires 212.2140. to provide 9 (0.37 g, 47% yield, 76% Z as determined by 13C-NMR) as a colorless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure for compound 3, 11-eicosenol (1.3 g, 4.4 mmol) and 1-hexene (6 mL) in THF (6 mL) were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, td, J=6.5, 5.3 Hz), 2.02 (4H, m), 1.56 (2H, m), 1.23-1.38 (19H, m), 0.90 (3H, t, J=7.2 Hz); 13C NMR (CDCl3): δ 129.9 (2C), 63.1, 32.8, 32.0, 29.8, 29.6 (2C), 29.5, 29.4, 29.3, 27.2, 26.9, 25.8, 22.4, 14.0; HRMS (FAB): 241.2536, [C16H32O+H]+ requires 241.2531. were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure for compound 3, 11-eicosenol (1.3 g, 4.4 mmol) and 1-hexene (6 mL) in THF (6 mL) were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, td, J=6.5, 5.3 Hz), 2.02 (4H, m), 1.56 (2H, m), 1.23-1.38 (19H, m), 0.90 (3H, t, J=7.2 Hz); 13C NMR (CDCl3): δ 129.9 (2C), 63.1, 32.8, 32.0, 29.8, 29.6 (2C), 29.5, 29.4, 29.3, 27.2, 26.9, 25.8, 22.4, 14.0; HRMS (FAB): 241.2536, [C16H32O+H]+ requires 241.2531. were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure for compound 7, 11-eicosenol (1.1 g, 3.7 mmol) and THF (3 mL) were reacted with 1 (0.047 g, 2 mol %) and 1-butene to provide 9 (0.37 g, 47% yield, 76% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.45 (2H, m), 3.63 (2H, t, J=6.6 Hz), 1.94-2.06 (4H, m), 1.56 (2H, dt, J=13.5, 6.7 Hz), 1.27, (15H, m), 0.96 (3H, m); 13C NMR (CDCl3): δ 131.7, 129.5, 63.2, 33.0, 29.9, 29.7, 29.7, 29.7, 29.6, 29.4, 27.2, 25.9, 20.7, 14.6; HRMS (FAB): 212.2135, [C14H28O]+ requires 212.2140. to provide 9 (0.37 g, 47% yield, 76% Z as determined by 13C-NMR) as a colorless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure for compound 3, 11-eicosenol (1.3 g, 4.4 mmol) and 1-hexene (6 mL) in THF (6 mL) were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, td, J=6.5, 5.3 Hz), 2.02 (4H, m), 1.56 (2H, m), 1.23-1.38 (19H, m), 0.90 (3H, t, J=7.2 Hz); 13C NMR (CDCl3): δ 129.9 (2C), 63.1, 32.8, 32.0, 29.8, 29.6 (2C), 29.5, 29.4, 29.3, 27.2, 26.9, 25.8, 22.4, 14.0; HRMS (FAB): 241.2536, [C16H32O+H]+ requires 241.2531. were reacted with 1 (0.028 g, 1 mol %) to provide 5 (0.84 g, 76% yield, 86% Z as determined by 1H-NMR) as a colorless oil