Y. Fujii et al.
Bull. Chem. Soc. Jpn., 78, No. 3 (2005)
461
(neat) 1093, 1371, 1468, 2854, 2924 cmꢂ1
;
1H NMR (CDCl3) ꢀ
3.17 (m, 1H), 3.40 (t, 2H, J ¼ 6:4 Hz); 13C NMR (CDCl3) ꢀ
14.47, 23.11, 24.56, 26.32, 26.70, 29.81, 29.95, 30.07 (2C),
30.11 (2C), 30.13, 30.14, 30.68 (2C), 32.35, 32.70 (2C), 68.16,
77.55; HRMS (EI) Found: m=z 296.3067 (Mþ). Calcd for
C20H40O: M, 296.3079.
0.89 (t, 3H, J ¼ 7:2 Hz), 0.92 (d, 6H, J ¼ 6:4 Hz), 1.11 (d, 3H,
J ¼ 6:8 Hz), 1.12–1.38 (m, 26H), 1.43–1.60 (m, 4H), 1.77 (m,
1H), 3.20–3.60 (m, 3H); 13C NMR (CDCl3) ꢀ 14.28, 20.14,
22.72, 22.91, 23.26, 24.83, 26.50, 29.60, 29.73, 29.86 (2C),
29.90 (2C), 29.94 (4C), 30.46, 32.16, 46.61, 68.65, 73.63; HRMS
(CI) Found: m=z 327.3641 ðM þ HÞþ. Calcd for C22H46O: M þ H,
327.3627.
Dodecyl 3,3,5-Trimethylcyclohexyl Ether (3k): Colorless
oil; IR (neat) 1093, 1344, 1456, 2854, 2923 cmꢂ1 1H NMR
;
(CDCl3) ꢀ 0.75–1.08 (m, 2H), 0.86 (s, 3H), 0.86 (d, 3H, J ¼ 6:4
Hz), 0.89 (t, 3H, J ¼ 6:8 Hz), 1.05 (s, 3H), 1.20–1.44 (m, 20H),
1.48–1.96 (m, 5H), 3.22–3.59 (m, 3H); 13C NMR (CDCl3) ꢀ
14.55, 23.15, 23.20, 23.60, 26.82, 27.67, 29.85, 30.00, 30.13
(3C), 30.17, 30.66, 31.19, 32.40, 34.63, 39.62, 41.04, 49.31,
60.51, 75.53; HRMS (EI) Found: m=z 310.3204 (Mþ). Calcd for
C21H42O: M, 310.3236.
2-Methylpropyl Tetradecyl Ether (3c): Colorless oil; IR
(neat) 1117, 1381, 1468, 2854, 2925 cmꢂ1 1H NMR (CDCl3) ꢀ
;
0.89 (t, 3H, J ¼ 6:8 Hz), 0.90 (d, 6H, J ¼ 6:8 Hz), 1.19–1.38
(m, 22H), 1.59 (m, 2H), 1.87 (m, 1H), 3.16 (d, 2H, J ¼ 6:4 Hz),
3.40 (t, 2H, J ¼ 6:8 Hz); 13C NMR (CDCl3) ꢀ 14.27, 19.58
(2C), 22.91, 26.43, 28.65, 29.60, 29.74, 29.86 (2C), 29.91 (2C),
29.92 (2C), 29.99, 32.16, 71.27, 78.03; HRMS (CI) Found: m=z
271.3029 ðM þ HÞþ. Calcd for C18H38O: M þ H, 271.3001.
Dioctyl Ether (3d): Colorless oil; IR (neat) 1115, 1377, 1468,
Octyl 1-Phenylethyl Ether (3l): Colorless oil; IR (neat) 700,
1
760, 1105, 1452, 2856, 2927 cmꢂ1; H NMR (CDCl3) ꢀ 0.99 (t,
3H, J ¼ 6:4 Hz), 1.30–1.50 (m, 10H), 1.52 (d, 3H, J ¼ 6:4 Hz),
1.67 (m, 2H), 3.38 (t, 3H, J ¼ 6:8 Hz), 4.45 (q, 1H, J ¼ 6:4
Hz), 7.27–7.41 (m, 5H); 13C NMR (CDCl3) ꢀ 14.63, 23.22,
24.80, 26.78, 29.84, 30.00, 30.53, 32.39, 69.12, 78.33, 126.31
(2C), 127.47, 128.56 (2C), 144.57; HRMS (EI) Found: m=z
234.1996 (Mþ). Calcd for C16H26O: M, 234.1984.
1
2856, 2925 cmꢂ1; H NMR (CDCl3) ꢀ 0.89 (t, 6H, J ¼ 6:8 Hz),
1.18–1.38 (m, 20H), 1.58 (m, 4H), 3.40 (t, 4H, J ¼ 6:8 Hz);
13C NMR (CDCl3) ꢀ 14.01 (2C), 22.63 (2C), 26.19 (2C), 29.26
(2C), 29.45 (2C), 29.77 (2C), 31.82 (2C), 70.93 (2C). These spec-
tral data agreed with those of an authentic sample (Aldrich).
Butyl Decyl Ether (3e): Colorless oil; IR (neat) 1120, 1377,
2,2-Dimethylpropyl Octyl Ether (3m): Colorless oil; IR
(neat) 1119, 1466, 2854, 2927 cmꢂ1 1H NMR (CDCl3) ꢀ 0.88
;
1
1466, 2854, 2925 cmꢂ1; H NMR (CDCl3) ꢀ 0.86 (t, 3H, J ¼ 7:6
Hz), 0.90 (t, 3H, J ¼ 7:6 Hz), 1.18–1.41 (m, 16H), 1.48–1.59 (m,
4H), 3.33–3.40 (m, 4H); 13C NMR (CDCl3) ꢀ 14.30, 14.47, 19.81,
23.10, 26.63, 29.75, 29.93, 30.00, 30.04, 30.21, 32.30, 32.32,
70.90, 71.24; HRMS (EI) Found: m=z 214.2290 (Mþ). Calcd for
C14H30O: M, 214.2297.
(t, 3H, J ¼ 6:8 Hz), 0.90 (s, 9H), 1.20–1.38 (m, 10H), 1.55 (m,
2H), 3.04 (s, 2H), 3.39 (t, 2H, J ¼ 6:0 Hz); 13C NMR (CDCl3)
ꢀ 14.52, 23.10, 26.63, 27.15 (3C), 29.75, 29.91, 30.11, 32.29,
32.46, 71.93, 81.66; HRMS (CI) Found: m=z 201.2206
ðM þ HÞþ. Calcd for C13H28O: M þ H, 201.2218.
Hexadecyl Octyl Ether (3f): White solid; mp 28.2 ꢃC; IR
(neat) 1117, 1377, 1466, 2854, 2923 cmꢂ1
1-Methylheptyl Octyl Ether (3n): Colorless oil; IR (neat)
;
1H NMR (CDCl3) ꢀ
1097, 1373, 1466, 2856, 2927 cmꢂ1 1H NMR (CDCl3) ꢀ 0.89
;
0.89 (t, 6H, J ¼ 7:6 Hz), 1.18–1.38 (m, 36H), 1.58 (m, 4H),
3.40 (t, 4H, J ¼ 7:2 Hz); 13C NMR (CDCl3) ꢀ 14.26, 14.28,
22.88, 22.91, 26.46 (2C), 29.53, 29.62, 29.72, 29.76, 29.87 (2C),
29.92 (2C), 29.95 (4C), 30.04 (2C), 32.08, 32.17, 71.17 (2C);
HRMS (CI) Found: m=z 355.3908 ðM þ HÞþ. Calcd for C24H50O:
M þ H, 355.3940.
(t, 6H, J ¼ 7:6 Hz), 1.12 (d, 3H, J ¼ 6:4 Hz), 1.19–1.42 (m,
18H), 1.53 (m, 4H), 3.20–3.56 (m, 3H); 13C NMR (CDCl3) ꢀ
14.24 (2C), 19.90, 22.84, 22.86, 25.81, 26.49, 29.52, 29.63,
29.68, 30.43, 32.06, 32.11, 36.98, 68.63, 75.52; HRMS (CI)
Found: m=z 243.2679 ðM þ HÞþ. Calcd for C16H34O: M þ H,
243.2688.
2-Butoxyethyl 2-(Octoxy)ethyl Ether (3g): Colorless oil; IR
2-(Perfluorohexyl)ethyl 1,3-Dimethylbutyl Ether (3o): Col-
orless oil; IR (neat) 1146, 1242, 1369, 2962 cmꢂ1 1H NMR
;
1
(neat) 1119, 1466, 2856, 2925 cmꢂ1; H NMR (CDCl3) ꢀ 0.89 (t,
3H, J ¼ 6:8 Hz), 0.91 (t, 3H, J ¼ 7:2 Hz), 1.20–1.43 (m, 12H),
1.57 (m, 4H), 3.46 (m, 4H), 3.55–3.67 (m, 8H); 13C NMR (CDCl3)
ꢀ 14.02, 14.19, 19.42, 22.79, 26.26, 29.42, 29.60, 29.81, 31.88,
31.98, 70.26 (2C), 70.81 (2C), 71.30, 71.63; HRMS (CI) Found:
m=z 275.2623 ðM þ HÞþ. Calcd for C16H34O3: M þ H, 275.2586.
2-Butoxyethyl 2-Ethoxyethyl Ether (3h): Colorless oil; IR
(CDCl3) ꢀ 0.89 (d, 3H, J ¼ 6:4 Hz), 0.90 (d, 3H, J ¼ 6:4 Hz),
1.14 (d, 3H, J ¼ 6:0 Hz), 1.16 (m, 1H), 1.48 (m, 1H), 1.73 (m,
1H), 2.37 (m, 2H), 3.49 (m, 1H), 3.61 (dt, 1H, J ¼ 9:6, 6.4 Hz),
3.80 (dt, 1H, J ¼ 9:6, 6.4 Hz); 13C NMR (CDCl3) ꢀ 19.59,
22.43, 22.91, 24.56, 31.96 (t, J ¼ 21:4 Hz), 46.11, 60.05, 74.40,
107.24 (m), 109.60 (m), 112.30 (m), 114.50 (m), 117.21 (m),
119.90 (m); HRMS (CI) Found: m=z 449.1144 ðM þ HÞþ. Calcd
for C14H17OF13: M þ H, 449.1150.
(neat) 1117, 1350, 1458, 2868, 2933 cmꢂ1 1H NMR (CDCl3) ꢀ
;
0.86 (t, 3H, J ¼ 7:6 Hz), 1.16 (t, 3H, J ¼ 7:2 Hz), 1.32 (m,
2H), 1.52 (m, 2H), 3.41 (t, 2H, J ¼ 6:8 Hz), 3.48 (q, 2H, J ¼
7:2 Hz), 3.52–3.63 (m, 8H); 13C NMR (CDCl3) ꢀ 13.59, 14.83,
18.99, 31.45, 66.30, 69.58, 69.82, 70.36, 70.39, 70.87; HRMS
(CI) Found: m=z 191.1633 ðM þ HÞþ. Calcd for C10H22O3:
M þ H, 191.1647.
2-(Perfluorohexyl)ethyl Octyl Ether (3p): Colorless oil; IR
1
(neat) 1146, 1240, 1365, 2931 cmꢂ1; H NMR (CDCl3) ꢀ 0.88 (t,
3H, J ¼ 7:2 Hz), 1.20–1.38 (m, 10H), 1.57 (m, 2H), 2.40 (m, 2H),
3.44 (t, 2H, J ¼ 6:8 Hz), 3.70 (t, 2H, J ¼ 7:2 Hz); 13C NMR
(CDCl3) ꢀ 13.88, 22.72, 26.18, 29.38, 29.53, 29.70, 31.67 (t, J ¼
22:2 Hz), 31.95, 62.56, 71.53, 108.48 (m), 110.98 (m), 113.08
(m), 115.67 (m), 118.36 (m), 121.07 (m); HRMS (CI) Found:
m=z 477.1482 ðM þ HÞþ. Calcd for C16H21OF13: M þ H,
477.1463.
2-(Perfluorooctyl)ethyl 3,5,5-Trimethylhexyl Ether (3q):
;
Colorless oil; IR (neat) 1146, 1240, 1365, 2958 cmꢂ1 1H NMR
(CDCl3) ꢀ 0.89 (s, 9H), 0.93 (d, 3H, J ¼ 6:8 Hz), 1.07 (dd, 1H,
J ¼ 14:0, 6.0 Hz), 1.23 (dd, 1H, J ¼ 14:0, 3.2 Hz), 1.36–1.47
(m, 1H), 1.53–1.67 (m, 2H), 2.40 (m, 2H), 3.46 (t, 2H, J ¼ 6:8
Hz), 3.69 (t, 2H, J ¼ 6:8 Hz); 13C NMR (CDCl3) ꢀ 22.65,
1,6-Bis(1,3-dimethylbutoxy)hexane (3i): Colorless oil; IR
(neat) 1093, 1371, 1468, 2868, 2956 cmꢂ1 1H NMR (CDCl3) ꢀ
;
0.91 (d, 12H, J ¼ 7:2 Hz), 1.12 (d, 6H, J ¼ 6:0 Hz), 1.15–1.92
(m, 14H), 3.20–3.60 (m, 6H); 13C NMR (CDCl3) ꢀ 19.68 (2C),
22.28 (2C), 22.76 (2C), 24.36 (2C), 25.86 (2C), 29.91 (2C),
46.10 (2C), 68.06 (2C), 73.18 (2C); HRMS (CI) Found: m=z
287.2934 ðM þ HÞþ. Calcd for C18H38O2: M þ H, 287.2950.
Cyclohexyl Tetradecyl Ether (3j): Colorless oil; IR (neat)
1109, 1363, 1452, 2854, 2925 cmꢂ1
;
1H NMR (CDCl3) ꢀ 0.88
(t, 3H, J ¼ 6:8 Hz), 1.14–1.42 (m, 27H), 1.46–1.94 (m, 7H),