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Organic & Biomolecular Chemistry
Page 5 of 9
DOI: 10.1039/C7OB00872D
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White solid, mp 83-85 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm) 26.3, 22.5, 14.3. HRMS (ESI): calcd. for C13H19NNaO2 [M+Na]+,
244.1313, found: 244.1309.
7.59 (d, J=4.1 Hz, 1H), 7.37 (t, J=8.3 Hz, 2H), 7.19 (t, J=7.4 Hz, 1H),
7.09 (d, J=7.5 Hz, 2H), 2.67 (d, J=4.6 Hz, 3H). 13C-NMR (100 MHz,
DMSO-d6): 155.3, 151.5, 129.6, 125.3, 122.2, 27.5. HRMS (ESI):
calcd. for C8H9NNaO2 [M+Na]+, 174.0531, found: 174.0536.
Phenyl cyclohexyl carbamate(9)
White solid, mp 138-140 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.69 (d, J=7.8 Hz, 1H), 7.36 (t, J=8.1 Hz, 2H), 7.18 (t, J=7.4 Hz, 1H),
7.08 (d, J=7.5 Hz, 2H), 3.36-3.26 (m, 1H), 1.83-1.54 (m, 5H), 1.28-
1.09 (m, 5H). 13C-NMR (100 MHz, DMSO-d6): 153.9, 151.5, 129.6,
125.2, 122.2, 50.2, 32.9, 25.5, 25.0. HRMS (ESI): calcd. for
C13H17NNaO2 [M+Na]+, 242.1157, found: 242.1154.
Phenyl ethyl carbamate (3)
White solid, mp 48-50 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.71 (t, J=4.8 Hz, 1H), 7.36 (t, J=8.2 Hz, 2H), 7.18 (t, J=7.4 Hz, 1H),
7.08 (d, J=7.6 Hz, 2H), 3.09 (quintet, J=7.1 Hz, 2H), 1.08 (t, J=7.2 Hz,
3H). 13C-NMR (100 MHz, DMSO-d6): 154.6, 151.5, 129.6, 125.2,
122.2, 35.7, 15.3. HRMS (ESI): calcd. for C9H11NNaO2 [M+Na]+,
188.0687, found: 188.0687.
Phenyl ((1r,4r)-4-methylcyclohexyl)carbamate (10)
White solid, mp 175-177 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.68 (d, J=7.9 Hz, 1H), 7.36 (t, J=8.1 Hz, 2H), 7.18 (t, J=7.3 Hz, 1H),
7.08 (d, J=7.6 Hz, 2H), 3.34-3.18 (m, 1H), 1.85 (d, J=10.1 Hz, 2H),
1.67 (d, J=12.2 Hz, 2H), 1.29-1.22 (m, 3H), 1.03-0.91 (m, 2H), 0.86
(d, J=6.4 Hz, 3H). 13C-NMR (100 MHz, DMSO-d6): 153.9, 151.5,
129.6, 125.2, 122.2, 50.3, 33.9, 32.8, 31.8, 22.6. HRMS (ESI): calcd.
for C14H19NNaO2 [M+Na]+, 256.1313, found: 256.1309.
Phenyl propyl carbamate (4)
White solid, mp 56-58 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.73 (t, J=5.4 Hz, 1H), 7.36 (t, J=8.3 Hz, 2H), 7.18 (t, J=7.4 Hz, 1H),
7.08 (d, J=7.5 Hz, 2H), 3.03 (quartet, J=6.9 Hz, 2H), 1.48 (sextet,
J=7.2 Hz, 2H), 0.88 (t, J=7.4 Hz, 3H). 13C-NMR (100 MHz, DMSO-d6):
154.8, 151.5, 129.6, 125.2, 122.1, 42.6, 22.9, 11.6. HRMS (ESI):
calcd. for C10H13NNaO2 [M+Na]+, 202.0844, found: 202.0840.
Phenyl octyl carbamate (11)
White solid, mp 40-42 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.72 (t, J=5.6 Hz, 1H), 7.36 (t, J=8.2 Hz, 2H), 7.18 (t, J=7.4 Hz, 1H),
7.08 (d, J=7.5 Hz, 2H), 3.04 (quartet, J=6.7 Hz, 2H), 1.46 (quintet,
J=6.8 Hz, 2H), 1.37-1.18 (m, 10H), 0.86 (t, J=7.0 Hz, 3H). 13C-NMR
(100 MHz, DMSO-d6): 154.7, 151.5, 129.6, 125.2, 122.1, 40.8, 31.7,
29.6, 29.2, 29.1, 26.7, 22.5, 14.4. HRMS (ESI): calcd. for
C15H23NNaO2 [M+Na]+, 272.1626, found: 272.1628.
Phenyl isopropyl carbamate (5)
White solid, mp 80-82 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.66 (d, J=7.6 Hz, 1H), 7.37 (t, J=8.2 Hz, 2H), 7.19 (t, J=7.4 Hz, 1H),
7.08 (d, J=7.6 Hz, 2H), 3.71-3.60 (m, 1H), 1.12 (d, J=6.5 Hz, 6H). 13C-
NMR (100 MHz, DMSO-d6): 153.9, 151.5, 129.6, 125.2, 122.2, 43.1,
22.8. HRMS (ESI): calcd. for C10H13NNaO2 [M+Na]+, 202.0846, found:
202.0846.
Phenyl benzyl carbamate (12)
White solid, mp 82-84 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
8.31 (t, J=6.1 Hz, 1H), 7.39-7.24 (m, 7H), 7.19 (t, J=7.8 Hz, 1H), 7.11
(d, J=7.7 Hz, 2H), 4.28 (d, J=6.1 Hz, 2H). 13C-NMR (100 MHz, DMSO-
d6): 155.1, 151.5, 139.7, 129.7, 128.8, 127.6, 127.4, 125.4, 122.2,
44.4. HRMS (ESI): calcd. for C14H13NNaO2 [M+Na]+, 250.0844, found:
250.0838.
Phenyl cyclopropyl carbamate (6)
White solid, mp 73-75 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.92 (br. s, 1H), 7.36 (t, J=7.9 Hz, 2H), 7.19 (t, J=7.3 Hz, 1H), 7.09 (d,
J=7.8 Hz, 2H), 2.55 (sextet, J=3.4 Hz, 1H), 0.65-0.51 (m, 4H). 13C-
NMR (100 MHz, DMSO-d6): 155.4, 151.4, 129.6, 125.3, 122.2, 23.5,
6.2. HRMS (ESI): calcd. for C10H11NNaO2 [M+Na]+, 200.0687, found:
200.0687.
Phenyl (1-phenylethyl) carbamate (13)
White solid, mp 105-107 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
8.35 (d, J=8.1 Hz, 1H), 7.39-7.33 (m, 6H), 7.24 (t, J=6.9 Hz, 1H), 7.18
(t, J=7.3 Hz, 1H), 7.08 (d, J=7.8 Hz, 2H), 4.73 (quintet, J=7.4 Hz, 1H),
1.42 (d, J=7.0 Hz, 3H). 13C-NMR (100 MHz, DMSO-d6): 154.1, 151.4,
145.0, 129.7, 128.8, 127.2, 126.3, 125.3, 122.2, 50.8, 23.2. HRMS
(ESI): calcd. for C15H15NNaO2 [M+Na]+, 264.1000, found: 264.0992.
Phenyl pentyl carbamate (7)
White solid, mp 48-50 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.72 (t, J=5.5 Hz, 1H), 7.37 (t, J=8.2 Hz, 2H), 7.19 (t, J=7.4 Hz, 1H),
7.09 (d, J=7.5 Hz, 2H), 3.05 (quartet, J=6.9 Hz, 2H), 1.47 (quintet,
J=7.1 Hz, 2H), 1.33-1.26 (m, 4H), 0.88 (t, J=7.0 Hz, 3H). 13C-NMR (100
MHz, DMSO-d6): 154.7, 151.6, 129.6, 125.2, 122.1, 40.8, 29.3, 28.9,
22.2, 14.3. HRMS (ESI): calcd. for C12H17NNaO2 [M+Na]+, 230.1157,
found: 230.1160.
Phenyl phenethyl carbamate (14)
White solid, mp 93-95 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.84 (t, J=5.5 Hz, 1H), 7.38-7.29 (m, 4H), 7.25-7.17 (m, 4H), 7.06 (d,
J=7.6 Hz, 2H), 3.29 (quartet, J=6.1 Hz, 2H), 2.79 (t, J=7.1 Hz, 2H). 13C-
NMR (100 MHz, DMSO-d6): 154.7, 151.5, 139.6, 129.6, 129.1, 128.8,
126.6, 125.3, 122.1, 42.4, 35.7. HRMS (ESI): calcd. for C15H15NNaO2
[M+Na]+, 264.1000, found: 264.0991.
Phenyl hexyl carbamate (8)
White solid, mp 44-46 °C; 1H-NMR (400 MHz, DMSO-d6): δ (ppm)
7.72 (t, J=5.4 Hz, 1H), 7.37 (t, J=8.1 Hz, 2H), 7.19 (t, J=7.3 Hz, 1H),
7.08 (d, J=7.6 Hz, 2H), 3.05 (quartet, J=6.8 Hz, 2H), 1.46 (quintet,
J=7.1 Hz, 2H), 1.35-1.22 (m, 6H), 0.87 (t, J=6.9 Hz, 3H). 13C-NMR (100
MHz, DMSO-d6): 154.7, 151.6, 129.6, 125.2, 122.1, 40.9, 31.4, 29.6,
Phenyl dimethylcarbamate (15)
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