Molecules 2019, 24, 2063
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31.59 (C-19), 31.25 (C-9), 25.41 (C-8), 23.75 (C-17), 22.57 (C-16, 18). ESIMS: m/z 366.2070 [M + H]+,
388.1886 [M + Na]+, calculated for C23H27NO3 (365.47).
Cyclohexyl (E)-4-hydroxyimino-4-(4-methylphenyl)butanoate (4B-1). Colorless crystal, yield
88.2%. m.p. 80.1–80.7 ◦C. 1H NMR (MeOD)
δ 7.51 (d, J = 8.2 Hz, 2H, H-2, 6), 7.20 (d, J = 8.0 Hz, 2H,
H-3, 5), 4.70 (dt, J = 8.7, 4.5 Hz, 1H, H-15), 3.08-3.05 (m, 2H, H-8), 2.54 (t, J = 7.9 Hz, 2H, H-9), 2.36 (s,
3H, H-14), 1.80 (d, J = 9.3 Hz, 2H, H-16), 1.75–1.71 (m, 2H, H-20), 1.57–1.54 (m, 1H, H-18), 1.39 (dd,
J = 17.8, 8.7 Hz, 4H, H-17, 19), 1.32 (d, J = 11.5 Hz, 1H, H-18). 13C NMR (CDCl3)
δ 172.15 (C-10), 158.23
(C-7), 139.48 (C-1), 132.32 (C-4), 129.35 (C-2, 6), 126.24 (C-3, 5), 72.96 (C-15), 31.57 (C-16, 20), 31.06
(C-9), 25.37 (C-8), 23.73 (C-18), 21.89 (C-17, 19), 21.27 (C-14). ESIMS: m/z 290.1754 [M + H]+, 312.1573
[M + Na]+, calculated for C17H23NO3 (289.38).
Cyclohexyl (E)-4-methoxyimino-4-(4-methoxyphenyl)butanoate (4B-2). Colorless liquid, yield
1
81.7%. H NMR (CDCl3)
δ 7.55 (d, J = 8.2 Hz, 2H, H-2, 6), 7.19 (d, J = 8.0 Hz, 2H, H-3, 5), 4.80–4.73 (m,
1H, H-15), 3.99 (s, 3H, H-22), 3.06-3.03 (m, 2H, H-8), 2.56–2.53 (m, 2H, H-9), 2.38 (s, 3H, H-14), 1.83 (dd,
J = 8.8, 3.8 Hz, 2H, H-20), 1.73 (dd, J = 9.0, 4.7 Hz, 2H, H-16), 1.55 (dd, J = 9.6, 6.5 Hz, 1H, H-18), 1.39
(dd, J = 22.4, 12.4 Hz, 4H, H-17, 19), 1.29–1.24 (m, 1H, H-18). 13C NMR (CDCl3)
δ 172.11 (C-10), 156.95
(C-7), 139.22 (C-4), 132.40 (C-1), 129.24 (C-2, 6), 126.22 (C-3, 5), 72.87 (C-15), 61.93 (C-22), 31.59 (C-16,
20), 31.27 (C-9), 25.39 (C-8), 23.73 (C-18), 22.34 (C-17, 19), 21.25 (C-14). ESIMS: m/z 326.1726 [M+Na]+,
calculated for C18H25NO3 (303.40).
Cyclohexyl (E)-4-benzyloxyimino-4-(4-methylphenyl)butanoate (4B-3). Pale yellow liquid, yield
1
79.3%. H NMR (CDCl3)
δ 7.37–7.29 (m, 7H, H-2, 6, 24, 25, 26, 27, 28), 7.22 (d, J = 7.9 Hz, 2H, H-3,
5), 5.09 (s, 2H, H-22), 4.74 (dt, J = 8.9, 4.6 Hz, 1H, H-15), 2.87–2.83 (m, 2H, H-8), 2.57–2.54 (m, 2H,
H-9), 2.38 (s, 3H, H-14), 1.84-1.78 (m, 2H, H-16), 1.72 (dd, J = 9.4, 3.6 Hz, 2H, H-20), 1.55 (dd, J = 6.9,
3.7 Hz, 1H, H-18), 1.41–1.33 (m, 4H, H-17, 19), 1.27 (t, J = 7.0 Hz, 1H, H-18). 13C NMR (CDCl3)
δ 172.16
(C-10), 155.68 (C-7), 138.81 (C-4), 138.41 (C-23), 130.80 (C-1), 128.86 (C-3, 5), 128.22 (C-25, 27), 127.89
(C-26), 127.82 (C-24, 28), 127.47 (C-2, 6), 75.89 (C-22), 72.64 (C-15), 31.61 (C-16, 20), 31.45 (C-9), 30.75
(C-8), 25.40 (C-18), 23.76 (C-17, 19), 21.37 (C-14). ESIMS: m/z 380.2223 [M + H]+, 402.2037 [M + Na]+,
calculated for C24H29NO3 (379.50).
Cyclohexyl (E)-4-hydroxyimino-4-(4-methoxyphenyl)butanoate (4C-1). Colorless crystal, yield
89.0%. m.p. 67.7–68.5 ◦C. 1H NMR (CDCl3)
δ 8.69 (s, 1H, H-23), 7.59 (d, J = 8.9 Hz, 2H, H-2, 6), 6.93 (d,
J = 8.9 Hz, 2H, H-3, 5), 4.79-4.75 (m, 1H, H-16), 3.85 (s, 3H, H-15), 3.13- 3.10 (m, 2H, H-8), 2.62-2.59
(m, 2H, H-9), 1.83 (dd, J = 8.8, 4.0 Hz, 2H, H-17), 1.72 (dd, J = 8.7, 3.7 Hz, 2H, H-21), 1.54 (dd, J = 5.7,
3.2 Hz, 1H, H-19), 1.38 (dd, J = 23.1, 11.8 Hz, 4H, H-18, 20), 1.26 (dd, J = 13.0, 3.1 Hz, 1H, H-19). 13C
NMR (CDCl3) δ 172.27 (C-10), 160.61 (C-4), 157.68 (C-7), 127.71 (C-2, 6), 127.63 (C-1), 114.05 (C-3, 5),
73.00 (C-16), 55.33 (C-15), 31.57 (C-17, 21), 31.08 (C-9), 25.37 (C-8), 23.73 (C-19), 21.95 (C-18, 20). ESIMS:
m/z 306.1701 [M + H]+, 328.1521 [M + Na]+, calculated for C17H23NO4 (305.37).
Cyclohexyl (E)-4-methoxyimino-4-(4-methoxyphenyl)butanoate (4C-2). Colorless liquid, yield
1
80.7%. H NMR (MeOD)
δ 7.59 (d, J = 8.9 Hz, 2H, H-2, 6), 6.94 (d, J = 8.9 Hz, 2H, H-3, 5), 4.72–4.64
(m, 1H, H-16), 3.95 (s, 3H, H-23), 3.83 (s, 3H, H-15), 3.03–2.97 (m, 2H, H-8), 2.52-2.46 (m, 2H, H-9),
1.82-1.76 (m, 2H, H-17), 1.74-1.67 (m, 2H, H-21), 1.55 (dd, J = 10.7, 4.6 Hz, 1H, H-19), 1.42-1.33 (m, 4H,
H-18,20), 1.29 (dd, J = 9.6, 3.0 Hz, 1H, H-19). 13C NMR (MeOD)
δ 172.28 (C-10), 160.78 (C-4), 156.67
(C-7), 127.48 (C-2, 6), 127.35 (C-1), 113.53 (C-3, 5), 72.89 (C-16), 60.84 (C-23), 54.42 (C-15), 31.16 (C-17,
21), 30.99 (C-9), 25.07 (C-8), 23.34 (C-19), 21.81 (C-18, 20). ESIMS: m/z 320.1845 [M + H]+, 342.1661
[M + Na]+, calculated for C18H25NO4 (319.40).
Cyclohexyl (E)-4-benzyloxyimino-4-(4-methoxyphenyl)butanoate (4C-3). Pale yellow liquid, yield
1
76.9%. H NMR (MeOD)
δ 7.58 (d, J = 8.9 Hz, 2H, H-2, 6), 7.41 (d, J = 7.1 Hz, 2H, H-25, 29), 7.36 (t,
J = 7.5 Hz, 2H, H-26, 28), 7.30 (t, J = 7.3 Hz, 1H, H-27), 6.92 (d, J = 8.9 Hz, 2H, H-3, 5), 5.19 (s, 2H, H-23),
4.66 (dt, J = 8.7, 4.5 Hz, 1H, H-16), 3.81 (s, 3H, H-15), 3.06-3.03 (m, 2H, H-8), 2.52-2.49 (m, 2H, H-9), 1.75
(dd, J = 13.6, 6.0 Hz, 2H, H-17), 1.68 (dd, J = 9.2, 4.9 Hz, 2H, H-21), 1.55–1.50 (m, 1H, H-19), 1.39–1.32
(m, 4H, H-18,20), 1.30–1.24 (m, 1H, H-19). 13C NMR (MeOD)
δ
172.35 (C-10), 160.82 (C-4), 157.11 (C-7),
138.08 (C-24), 127.99 (C-26, 28), 127.79 (C-2, 6), 127.52 (C-27), 127.43 (C-25, 29), 127.38 (C-1), 113.50 (C-3,