Molecules 2019, 24, 1458
7 of 11
J = 6.5 Hz, 4H), 3.77 (s, 6H), 1.85–1.74 (m, 4H), 1.59–1.46 (m, 4H); 13C NMR (126 MHz, CDCl3)
δ
153.68,
153.24, 115.42, 114.61, 68.48, 55.72, 29.32, 25.87; HRMS (ESI) calcd for C20H27O4 [M+H]+: 331.1909,
found: 331.1907.
Tetracosane (2b) was isolated as a white solid (Mp.: 45–46 ◦C) by silica-gel column chromatography
using hexane as an eluent; 1H NMR (400 MHz, CDCl3)
δ
1.32–1.23 (m, 44H), 0.88 (t, J = 6.7 Hz, 6H);
13C NMR (500 MHz, CDCl3)
δ 31.92, 29.70, 29.36, 22.69, 14.14, 14.10; all peaks were broad or multiplet;
HRMS (ESI) calcd for C24H50: 338.3913, found: 338.3920.
1,8-Diphenyloctane (2c) was isolated as a colorless oil by silica-gel column chromatography using
a mixture of Hexane and EtOAc (5:1) as an eluent; 1H NMR (400 MHz, CDCl3)
δ
7.32–7.22 (m, 6H),
7.21–7.12 (m, 4H), 2.63–2.55 (m, 4H), 1.60 (dt, J = 15.1, 7.4 Hz, 4H), 1.37–1.27 (m, 8H); 13C NMR
(500 MHz, CDCl3) 142.90, 128.38, 128.20, 125.53, 35.96, 31.49, 29.41, 29.29; HRMS (ESI) calcd for
δ
C24H50: 266.2035, found: 266.2035.
2,6,11,15-Tetramethylhexadeca-2,14-diene (2d) was isolated as a colorless oil by silica-gel column
1
chromatography using hexane as an eluent; H NMR (500 MHz, CDCl3)
δ 5.10 (t, J = 7.2 Hz, 2H),
2.04–1.87 (m, 4H), 1.68 (s, 6H), 1.60 (s, 6H), 1.44–1.18 (m, 10H), 1.17–1.03 (m, 4H), 0.85 (d, J = 6.6 Hz,
6H); 13C NMR (500 MHz, CDCl3)
δ
130.94, 125.10, 37.15, 36.99, 32.39, 27.34, 25.72, 25.57, 19.60, 17.62;
HRMS (ESI) calcd for C20H38: 278.2974, found: 278.2973.
5,11-Hexadecadiyne (2e) was isolated as a colorless oil by silica-gel column chromatography using
1
hexane as an eluent; H NMR (500 MHz, CDCl3)
δ
2.20–2.10 (m, 8H), 1.62–1.34 (m, 12H), 0.90 (t,
J = 7.2 Hz, 6H); 13C NMR (500 MHz, CDCl3)
δ 80.44, 79.78, 31.23, 28.24, 21.93, 18.42, 18.32, 13.63; HRMS
(ESI) calcd for C16H26: 218.2035, found: 218.2025.
1,4-Di(4-chlorophenyloxy)hexane (2f) was isolated as a white solid (Mp.: 78–79 ◦C) by silica-gel column
chromatography using chloroform as an eluent; 1H NMR (500 MHz, CDCl3)
δ
7.22 (d, J = 9.0 Hz, 4H),
6.81 (d, J = 9.0 Hz, 4H), 3.93 (t, J = 6.4 Hz, 4H), 1.80 (p, J = 6.3 Hz, 4H), 1.52 (dd, J = 7.2, 3.8 Hz, 4H);
13C NMR (500 MHz, CDCl3)
157.65, 129.26, 125.34, 115.71, 68.08, 29.10, 25.80; HRMS (ESI) calcd for
δ
C24H50: 338.0840, found: 338.0840.
1,6-Di(4-pinacolborylphenyloxy)hexane (2g) [49] was isolated as a white solid (Mp.: 139–140 ◦C) by
silica-gel column chromatography using chloroform as an eluent; 1H NMR (500 MHz, CDCl3)
δ 7.75 (d,
J = 8.56 Hz, 4H), 6.89 (d, J = 8.60 Hz, 4H), 3.99 (t, J = 7.5 Hz, 4H), 1.82 (t, J = 6.25 Hz, 4H) 1.54 (quin,
J = 3.75 Hz, 4H), 1.34 (s, 24H); 13C NMR (500 MHz, CDCl3) δ161.68, 136.50, 113.85, 83.51, 67.58, 29.15,
25.85, 24.86.
Diethyl dodecanedioate (2h) was isolated as a colorless oil by silica-gel column chromatography using
a mixture of hexane and EtOAc (3:1) as an eluent; 1H NMR (500 MHz, CDCl3)
δ
4.12 (t, J = 7.1 Hz
,
4H), 2.32–2.25 (m, 4H), 1.66–1.54 (m, 8H), 1.33–1.21 (m, 14H); 13C NMR (500 MHz, CDCl3)
δ
173.93,
60.14, 60.06, 34.37, 29.22, 29.11, 24.94, 14.22; HRMS (ESI) calcd for C16H31O4 [M+H]+: 287.2222,
found: 287.2221.
1,6-Diphthalimidylhexane (2i) [22] was isolated as a white solid (Mp.: 180–181 ◦C) by silica-gel column
chromatography using a mixture of hexane and EtOAc (3:1) as an eluent; 1H NMR (500 MHz, CDCl3)
δ
7.83 (dd, J = 5.4, 3.0 Hz, 4H), 7.70 (dd, J = 5.5, 3.0 Hz, 4H), 3.67 (t, J = 7.3 Hz, 4H), 1.67 (quint, J = 7.1
Hz, 4H), 1.38 (quint, J = 3.5 Hz, 4H); 13C NMR (500 MHz, CDCl3)
δ 168.42, 133.83, 132.14, 123.16, 37.87,
28.44, 26.41.
1,6-Di(tert-butyldimethylsilyloxy)hexane (2j) was isolated as a colorless oil by silica-gel column
chromatography using a mixture of hexane and EtOAc (10:1) as an eluent; 1H NMR (400 MHz, CDCl3)
δ
3.60 (t, J = 6.6 Hz, 4H), 1.51 (q, J = 6.7 Hz, 4H), 1.32 (ddd, J = 7.3, 4.5, 3.3 Hz, 4H), 0.89 (s, 18H), 0.04
(s, 12H); 13C NMR (126 MHz, CDCl3)
63.24, 32.86, 25.98, 25.61, 18.37, 5.27; HRMS (ESI) calcd for
C18H43O2Si2 [M+H]+: 347.2802, found: 347.2802.
δ
−