1538 Bull. Chem. Soc. Jpn. Vol. 83, No. 12 (2010)
Hydrophobic Effect and Substrate Specificity
N-Undecylheptanamide (3dg).
Mp 55.0-56.0 °C. IR
The authors must thank Prof. M. Tori and Ms. Y. Okamoto
of Tokushima-bunri University for the measurements of the
mass spectra.
1
(KBr): 1637 cm¹1. H NMR: ¤ 0.88 (6H, t-like, J = 6.9 Hz),
1.22-1.35 (22H, m), 1.44-1.67 (4H, m), 2.15 (2H, t, J =
7.5 Hz), 3.24 (2H, dt, J = 6.0, 7.0 Hz), 5.53 (1H, br). 13C NMR
(CDCl3, 77.0 ppm): ¤ 14.0, 14.1, 22.5, 22.6, 25.8, 26.9, 29.0,
29.3 (2C), 29.5, 29.6 (3C), 31.5, 31.9, 36.9, 39.4, 173.0.
EI-MS: m/z 283 (M+). Analysis Found: C, 76.24; H, 13.36;
N, 4.86%. Calcd for C18H37NO: C, 76.26; H, 13.16; N,
4.94%.
References
1
a) Organic Reactions in Water: Principles, Strategies and
Applications, ed. by U. M. Lindström, Blackwell Publishing,
N-Octadecylheptanamide (3di).
Mp 78.0-79.0 °C. IR
1
(KBr): 1637 cm¹1. H NMR: ¤ 0.88 (6H, t-like, J = 6.8 Hz),
1.23-1.35 (36H, m), 1.44-1.66 (4H, m), 2.15 (2H, t, J =
7.5 Hz), 3.23 (2H, dt, J = 6.0, 7.0 Hz), 5.53 (1H, br). 13C NMR
(CDCl3, 77.0 ppm): ¤ 14.0, 14.1, 22.5, 22.7, 25.8, 26.9, 29.0,
29.3 (2C), 29.5, 29.6 (3C), 29.7 (7C), 31.5, 31.9, 36.9, 39.4,
173.0. EI-MS: m/z 381 (M+). Analysis Found: C, 78.44; H,
13.54; N, 3.63%. Calcd for C25H51NO: C, 78.67; H, 13.47; N,
3.67%.
2
2809. d) J. B. F. N. Engberts, Organic Reactions in Water:
Principles, Strategies and Applications, ed. by U. M. Lindström,
Blackwell Publishing, Oxford, 2007, pp. 29-59.
3
N-Dodecyl-N-methyldodecanamide (7aa). A mixture of
¹1
4
stereoisomers. Mp 32.5-33.5 °C. IR (KBr): 1630 cm
.
1H NMR: ¤ 0.88 (6H, t-like, J = 6.9 Hz), 1.20-1.35 (34H,
m), 1.46-1.67 (4H, m), 2.28 (2H © 1/2, t, J = 7.6 Hz), 2.29
(2H © 1/2, t, J = 7.6 Hz), 2.90 (3H © 1/2, s), 2.96 (3H © 1/2,
s), 3.24 (2H © 1/2, t, J = 7.6 Hz), 3.34 (2H © 1/2, t, J =
7.6 Hz). 13C NMR (CDCl3, 77.0 ppm): ¤ 14.1 (2C), 22.7 (2C),
25.1 (1/2C), 25.5 (1/2C), 26.7 (1/2C), 26.9 (1/2C), 27.3 (1/
2C), 28.5 (1/2C), 29.3-29.6 (12C), 31.9 (2C), 33.0 (1/2C),
33.3 (1/2C), 33.7 (1/2C), 35.3 (1/2C), 47.7 (1/2C), 50.0
(1/2C), 172.9 (1/2C), 173.0 (1/2C). EI-MS: m/z 381 (M+),
225 ([M ¹ Me ¹ C10H21]+). Analysis Found: C, 78.51; H,
13.48; N, 3.62%. Calcd for C25H51NO: C, 78.67; H, 13.47; N,
3.67%.
5
6
7
8
N. Kunieda, M. Watanabe, K. Okamoto, M. Kinoshita,
K. Manabe, S. Iimura, X.-M. Sun, S. Kobayashi, J. Am.
9
13 A. J. Kell, A. Alizadeh, L. Yang, M. S. Workentin,
15 K. Tomioka, T. Sumiyoshi, S. Narui, Y. Nagaoka, A. Iida,
N-Dodecyl-N-methylacetamide (7ca).
A mixture of
stereoisomers. An oil. IR (neat): 1650 cm¹1. H NMR: ¤ 0.88
(3H, t-like, J = 6.6 Hz), 1.21-1.35 (18H, m), 1.46-1.61 (2H,
m), 2.07 (3H © 1/2, s), 2.09 (3H © 1/2, s), 2.91 (3H © 1/2, s),
2.98 (3H © 1/2, s), 3.25 (2H © 1/2, t, J = 7.6 Hz), 3.34
(2H © 1/2, t, J = 7.6 Hz). 13C NMR (CDCl3, 77.0 ppm): ¤
14.0, 21.1 (1/2C), 21.8 (1/2C), 22.6, 26.6 (1/2C), 26.8 (1/2C),
27.2 (1/2C), 28.2 (1/2C), 29.2-29.6 (6C), 31.8, 33.1 (1/2C),
35.9 (1/2C), 47.4 (1/2C), 50.8 (1/2C), 170.2. EI-MS: m/z 241
(M+), 226 ([M ¹ Me]+). HRMS: Found: m/z 241.2403. Calcd
for C15H31NO: M, 241.2406.
1
N-Dodecyl-N-methylheptanamide (7da). A mixture of
1
stereoisomers. An oil. IR (neat): 1650 cm¹1. H NMR: ¤ 0.88
(6H, t-like, J = 6.6 Hz), 1.20-1.36 (24H, m), 1.46-1.66 (4H,
m), 2.28 (2H © 1/2, t, J = 7.7 Hz), 2.30 (2H © 1/2, t,
J = 7.7 Hz), 2.91 (3H © 1/2, s), 2.96 (3H © 1/2, s), 3.24
(2H © 1/2, t, J = 7.7 Hz), 3.34 (2H © 1/2, t, J = 7.6 Hz).
13C NMR (Me4Si, 0.0 ppm): ¤ 14.1 (2C), 22.7 (2C), 25.2 (1/
2C), 25.6 (1/2C), 26.8 (1/2C), 26.9 (1/2C), 27.3 (1/2C), 28.5
(1/2C), 29.3-29.7 (7C), 31.9 (2C), 33.1 (1/2C), 33.3 (1/2C),
33.7 (1/2C), 35.3 (1/2C), 47.7 (1/2C), 50.0 (1/2C), 172.9 (1/
2C), 173.1 (1/2C). EI-MS: m/z 254 ([M ¹ C4H9]+), 226
([M ¹ C6H13]+). HRMS: Found: m/z 311.3179. Calcd for
C20H41NO: M, 311.3188.
20 O. Turinsky, R. A. Reck, U.S. Patent 2672470; O.
Turinsky, R. A. Reck, Chem. Abstr. 1955, 49, 20191.
22 C. C. Christopher, G. Johnson, L. J. Mathias, Polym. Prepr.
1995, 36, 402.