Cyclohexanone O-Butyl Oxime (3a)[26]
2-(Cyclohexylideneaminooxy)acetic Acid (3 f)[35]
Following the general procedure starting from 3 (0.57 g, 5 mmol),
oxime ether 3a was obtained as a pale-yellow oil (0.73 g, 86%).
1H NMR (400 MHz, CDCl3): d (ppm) 0.95 (t, J=7.2 Hz, 3H, CH3), 1.40
(tq, J=7.2 Hz, J=6.8 Hz, 2H, CH2 but.), 1.60–1.67 (m, 8H, 3CH2
cycl. + CH2 but.), 2.21 (m, 2H, CH2 cycl.), 2.45–2.52 (m, 2H, CH2 cycl.), 4.01
(t, J=6.8 Hz, 2H, OCH2). 13C NMR (100 MHz, CDCl3): d (ppm) 13.95
(CH3), 19.26 (CH2 but.), 25.26 (CH2 cycl.), 25.77 (CH2 cycl.), 25.87 (CH2 cycl.),
27.05 (CH2 cycl.), 31.17 (CH2 but.), 32.25 (CH2 cycl.), 73.00 (CH2 but.), 159.89
Following the general procedure starting from 3 (0.57 g, 5 mmol),
oxime ether 3 f was obtained as a pale yellow solid (0.77 g, 89%);
mp: 92.5–948C, lit. mp: 92–948C.[33] 1H NMR (700 MHz, CDCl3): d
(ppm) 1.59–1.69 (m, 6H, 3CH2 cycl.), 2.20 (m, 2H, CH2 cycl.), 2.52 (m,
2H, CH2 cycl.), 4.59 (s, 2H, OCH2), 10.26 (bs, 1H, COOH). 13C NMR
(100 MHz, CDCl3): d (ppm) 25.62 (CH2), 25.64 (CH2), 25.70 (CH2),
26.91 (CH2), 31.94 (CH2), 69.56 (OCH2), 163.37 (CC N), 175.13 (COOH).
=
MS (ESI): m/z 172 [M + H]+.
(CC N). MS (ESI): m/z 170 [M + H]+.
=
Propan-2-one O-butyl oxime (4a)
Cyclohexanone O-Naphthalen-1-ylmethyl Oxime (3b)
Following the general procedure starting from 4 (0.37 g, 5 mmol),
oxime ether 4a was obtained as a pale-yellow oil (0.55 g, 84%).
1H NMR (400 MHz, CDCl3): d (ppm) 0.95 (t, J=7.2 Hz, 3H, CH3), 1.42
(tq, J=7.2 Hz, J=6.4 Hz, 2H, CH2), 1.64 (tt, J=7.2 Hz, J=6.4 Hz,
2H, CH2), 1.88 (s, 3H, CH3), 1.91 (s, 3H, CH3), 4.05 (t, J=6.4 Hz, 2H,
OCH2). 13C NMR (100 MHz, CDCl3): d (ppm) 13.93 (CH2), 15.54 (CH3),
Following the general procedure starting from 3 (0.57 g, 5 mmol),
oxime ether 3b was obtained as a yellow oil (1.20 g, 94%). H NMR
1
(400 MHz, CDCl3): d (ppm) 1.58–1.71 (m, 6H, 3CH2 cycl.), 2.26 (m,
2H, CH2 cycl.), 2.50 (m, 2H, CH2 cycl.), 5.54 (s, 2H, OCH2), 7.45–7.57 (m,
4H, CH), 7.83 (d, J=8.0 Hz, 1H, CH), 7.88 (dd, J=8.0 Hz, J=1.6 Hz,
1H, CH), 8.13 (dd, J=8.0 Hz, J=1.6 Hz, 1H, CH). 13C NMR (100 MHz,
CDCl3): d (ppm) 25.52 (CH2), 25.82 (CH2), 25.83 (CH2), 27.09 (CH2),
32.26 (CH2), 73.73 (OCH2), 124.21 (CH), 125.31 (CH), 125.67 (CH),
126.07 (CH), 126.67 (CH), 128.50 (CH), 128.58 (CH), 131.91 (C),
19.23 (CH2), 21.84 (CH3), 31.24 (CH2), 73.18 (OCH2), 154.53 (CC N).
=
HRMS (ESI): m/z calcd for C7H16NO [M + H]+ 130.1232, found
130.1227.
133.67 (C), 133.72 (C), 161.16 (CC N). HRMS (ESI): m/z calcd for
=
Propan-2-one O-Naphthalen-1-ylmethyl Oxime (4b)[36]
C17H20NO [M + H]+ 254.1545, found 254.1540.
Following the general procedure starting from 4 (0.37 g, 5 mmol),
1
oxime ether 4b was obtained as a yellow oil (0.97 g, 91%). H NMR
Cyclohexanone O-2-(Dimethylamino)ethyl Oxime (3c)
(400 MHz, CDCl3): d (ppm) 1.90 (s, 3H, CH3), 1.93 (s, 3H, CH3), 5.57
(s, 2H, OCH2), 7.45–7.58 (m, 4H, CH), 7.84 (d, J=8.0 Hz, 1H, CH),
7.90 (dd, J=8.0 Hz, J=2.0 Hz, 1H, CH), 8.16 (dd, J=8.0 Hz, J=
1.2 Hz, 1H, CH). 13C NMR (100 MHz, CDCl3): d (ppm) 15.78 (CH3),
21.92 (CH3), 73.87 (OCH2), 124.18 (CH), 125.31 (CH), 125.69 (CH),
126.10 (CH), 126.74 (CH), 128.52 (CH), 128.64 (CH), 131.91 (C),
Following the general procedure starting from 3 (0.57 g, 5 mmol),
oxime ether 3c was obtained as a pale-yellow oil (0.84 g, 91%).
1H NMR (400 MHz, CDCl3): d (ppm) 1.57–1.70 (m, 6H, 3CH2 cycl.),
2.18–2.22 (m, 2H, CH2 cycl.), 2.31 (s, 6H, 2CH3, NCH3), 2.47 (m, 2H,
CH2 cycl.), 2.62 (t, J=6.0 Hz, 2H, CH2, NCH2), 4.13 (t, J=6.0 Hz, 2H,
CH2, OCH2). 13C NMR (100 MHz, CDCl3): d (ppm) 25.42 (CH2), 25.73
(CH2), 25.82 (CH2), 27.02 (CH2), 32.19 (CH2), 45.91 (2CH3, NCH3),
133.62 (C), 133.73 (C), 155.53 (CC N). MS (ESI): m/z 214 [M + H]+.
=
Propan-2-one O-2-(Dimethylamino)ethyl Oxime (4c)[37]
58.10 (NCH2), 71.37 (OCH2), 160.29 (CC N). HRMS (ESI): m/z calcd for
=
C10H21N2O [M + H]+ 185.1654, found 185.1651.
Following the general procedure starting from 4 (0.37 g, 5 mmol),
1
oxime ether 4c was obtained as a yellow oil (0.61 g, 85%). H NMR
(400 MHz, CDCl3): d (ppm) 1.87 (s, 3H, CH3), 1.88 (s, 3H, CH3), 2.33
(s, 6H, 2CH3, NCH3), 2.64 (t, J=5.6 Hz, 2H, NCH2), 4.16 (t, J=
5.6 Hz, 2H, OCH2).
Cyclohexanone O-3-(Dimethylamino)propyl Oxime (3d)
Following the general procedure starting from 3 (0.57 g, 5 mmol),
oxime ether 3d was obtained as a pale-yellow oil (0.90 g, 91%).
1H NMR (400 MHz, CDCl3): d (ppm) 1.59–1.67 (m, 6H, 3CH2 cycl.),
1.83 (tt, J=7.6 Hz, J=6.4 Hz, 2H, CH2), 2.20 (m, 2H, CH2 cycl.), 2.24 (s,
6H, 2CH3, NCH3), 2.36 (t, J=7.6 Hz, 2H, CH2), 2.46 (m, 2H, CH2
cycl.), 4.04 (t, J=6.4 Hz, 2H, OCH2). 13C NMR (100 MHz, CDCl3): d
(ppm) 25.26 (CH2), 25.76 (CH2), 25.85 (CH2), 27.04 (CH2), 27.40 (CH2),
32.22 (CH2), 45.46 (2CH3, NCH3), 56.59 (NCH2), 71.35 (OCH2),
13C NMR (100 MHz, CDCl3): d (ppm) 15.69 (CH3), 21.83 (CH3), 45.86
(2CH3, NCH3), 58.14 (NCH2), 71.38 (OCH2), 154.79 (CC N). MS (ESI):
=
m/z 145 [M + H]+.
Propan-2-one O-3-(Dimethylamino)propyl Oxime (4d)[31]
160.11 (CC N). HRMS (ESI): m/z calcd for C11H23N2O [M + H]+
=
Following the general procedure starting from 4 (0.37 g, 5 mmol),
oxime ether 4d was obtained as a pale-yellow oil (0.69 g, 87%).
1H NMR (400 MHz, CDCl3): d (ppm) 1.84 (t, J=6.4 Hz, 2H, CH2), 1.86
(s, 3H, CH3), 1.88 (s, 3H, CH3), 2.26 (s, 6H, 2CH3, NCH3), 2.39 (t, J=
7.6 Hz, 2H, NCH2), 4.06 (t, J=6.4 Hz, 2H, OCH2). 13C NMR (100 MHz,
CDCl3): d (ppm) 15.49 (CH3), 21.84 (CH3), 27.40 (CH2), 45.38 (2CH3,
199.1810, found 199.1808.
Cyclohexanone O-2-Morpholinoethyl Oxime (3e)[22]
Following the general procedure starting from 3 (0.57 g, 5 mmol),
oxime ether 3e was obtained as a light red oil (1.02 g, 90%).
1H NMR (400 MHz, CDCl3): d (ppm) 1.58–1.60 (m, 6H, 3CH2 cycl.),
2.19 (m, 2H, CH2), 2.45 (m, 2H, CH2 cycl.), 2.54 (t, J=4.8 Hz, 4H, 2
NCH2 mor.), 2.68 (t, J=6.0 Hz, 2H, NCH2), 3.73 (t, J=4.8 Hz, 4H, 2
OCH2 mor.), 4.17 (t, J=6.0 Hz, 2H, OCH2). 13C NMR (100 MHz, CDCl3):
d (ppm) 25.45 (CH2), 25.76 (CH2), 25.81 (CH2), 27.04 (CH2), 32.17
(CH2), 54.02 (CH2, 2NCH2 mor.), 57.46 (NCH2), 66.94 (CH2, 2OCH2
NCH3), 56.54 (NCH2), 71.40 (OCH2), 154.51 (CC N). MS (ESI): m/z 159
=
[M + H]+.
Propan-2-one O-2-Morpholinoethyl Oxime (4e)[38]
Following the general procedure starting from 4 (0.37 g, 5 mmol),
oxime ether 4e was obtained as a light red oil (0.80 g, 86%).
1H NMR (400 MHz, CDCl3): d (ppm) 1.84 (s, 3H, CH3), 1.87 (s, 3H,
mor.), 71.00 (OCH2), 160.46 (CC N). MS (ESI): m/z 227 [M + H]+.
=
ChemistryOpen 2018, 7, 551 –557
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ꢀ 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim