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Organic & Biomolecular Chemistry
Page 6 of 9
DOI: 10.1039/C7OB02947K
ARTICLE
Journal Name
7.14–7.19 (m, 1H), 7.49 (t, J = 7.5 Hz, 2H), 7.58 (t, J = 7.3 Hz, 6.13 (m, 1H), 6.89 (d, J = 8.9 Hz, 2H), 7.46 (d, J = 8.9 Hz, 2H).13C
1H), 7. 64–7. 71 (m, 4H), 7.98–8.02 (m, 2H). 13C NMR (101 NMR (101 MHz, CDCl3): δ 14.50, 17.78, 55.46, 59.85, 113.93,
MHz, CDCl3): δ 18.97, 123.87, 124.11 (q, J = 273.2 Hz), 125.73 115.43, 127.79, 134.44, 155.01, 160.53, 167.22.
(q, J = 3.7 Hz), 126.97, 128.47, 128.80, 131.00 (q, J = 32.7 Hz),
ethyl (E)-3-(p-tolyl)but-2-enoate 21
. Eluent: petroleum ether
1
133.02, 139.01, 146.43, 153.10, 191.86. HR-MS: m/z /EtOAc (200:1 v/v). Colorless oil, yield 52 mg (85%). H NMR
291.09991 [M+H]+; calcd for C17H14F3O, 291.09913.
3-(4-(dimethylamino)phenyl)cyclopent-2-en-1-one.9a
(400 MHz, CDCl3): δ 1.31 (t, J = 7.1 Hz, 3H), 2.36 (s, 3H), 2.57 (d,
J = 1.2 Hz, 2H), 4.21 (q, J = 7.1 Hz, 2H), 6.10–6.15 (m, 1H), 7.18
Eluent: petroleum ether/EtOAc (5:1 v/v). White solid, yield (d, J = 8.0 Hz, 2H), 7.39 (d, J = 8.2 Hz, 2H). 13C NMR (101 MHz,
53.2 mg (88%). 1H NMR (400 MHz, CDCl3): δ 2.51–2.58 (m, 2H), CDCl3): δ 14.48, 17.92, 21.30, 59.88, 116.39, 126.33, 129.30,
2.97–3.03 (m, 2H), 3.05 (s, 6H), 6.40 (s, 1H), 6.70 (d, J = 9.0 Hz, 139.24, 155.53, 167.12.
2H), 7.56 (d, J = 9.0 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ
ethyl
3-(4-(trifluoromethyl)phenyl)but-2-enoate.21,24
28.50, 35.25, 40.18, 111.52, 121.51, 122.98, 128.67, 152.38, Eluent: petroleum ether/EtOAc (200:1 v/v). Colorless oil,
(E)/(Z) ratio 45:1, yield 57.7 mg (74%). 1H NMR (400 MHz,
174.67, 209.51.
3-(4-methoxyphenyl)cyclopent-2-en-1-one.9a,23
Eluent: CDCl3): δ 1.33 (t, J = 7.1 Hz, 3H), 2.58 (d, J = 1.3 Hz, 3H), 4.23 (q,
petroleum ether/EtOAc (10:1 v/v). Light yellow solid, yield 46.2 J = 7.1 Hz, 2H), 6.11–6.18 (m, 1H), 7.57 (d, J = 8.4 Hz, 2H), 7.63
mg (82%). 1H NMR (400 MHz, CDCl3): δ 2.53–2.62 (m, 2H), (d, J = 8.3 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ 14.42, 18.07,
2.98–3.06 (m, 2H), 3.87 (s, 3H), 6.48 (t, J = 1.5 Hz, 1H), 6.97 (d, 60.25, 119.08, 124.09 (q, J = 273.4 Hz), 125.60 (q, J = 3.7 Hz),
J = 8.8, Hz, 2H), 7.63 (d, J = 8.8, Hz, 2H). 13C NMR (101 MHz, 126.80, 130.91 (q, J = 32.8 Hz), 145.92, 153.91, 166.55.
CDCl3): δ 28.71, 35.34, 55.56, 114.37, 125.59, 126.82, 128.72,
162.20, 173.77, 209.47.
ethyl (E)-3-(o-tolyl) but-2-enoate. Eluent: petroleum
ether/EtOAc (200:1 v/v). Colorless oil, yield 56.5 mg (92%). 1H
3-(p-tolyl)cyclopent-2-en-1-one.9a Eluent: petroleum ether NMR (400 MHz, CDCl3): δ 1.31 (t, J = 7.1 Hz, 3H), 2.29 (s, 3H),
/EtOAc (10:1 v/v). White solid, yield 39 mg (75%). 1H NMR (400 2.45 (d, J = 1.1 Hz, 3H), 4.21 (q, J = 7.1 Hz, 2H), 5.72–5.79 (m,
MHz, CDCl3): δ 2.41 (s, 3H), 2.53–2.61 (m, 2H), 2.98–3.08 (m, 1H), 7.07 (d, J = 7.1 Hz, 1H), 7.12–7.24 (m, 3H). 13C NMR (101
2H), 6.54 (t, J = 1.6 Hz, 1H), 7.26 (d, J = 8.0 Hz, 2H), 7.55 (t, J = MHz, CDCl3): δ 14.44, 19.83, 20.92, 59.94, 119.51, 125.83,
8.2 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ 21.65, 28.70, 35.34, 127.19, 127.79, 130.50, 133.98, 144.02, 158.38, 166.79.
126.72, 126.91, 129.72, 131.41, 141.95, 174.16, 209.57.
3-(4-(trifluoromethyl)phenyl)cyclopent-2-en-1-one 9b
ethyl (E)-3-(furan-2-yl)but-2-enoate 21
ether/EtOAc (200:1 v/v). Yellow oil, yield 37.6 mg ( 69%). 1H
.
Eluent: petroleum
.
Eluent: petroleum ether/EtOAc (10:1 v/v). White solid, yield NMR (400 MHz, CDCl3): δ 1.31 (t, J = 7.1 Hz, 3H), 2.46 (d, J = 1.1
33.8 mg (50%). 1H NMR (400 MHz, CDCl3): δ 2.58–2.68 (m, 2H), Hz, 3H), 4.20 (q, J = 7.1 Hz, 2H), 6.35–6.39 (m, 1H), 6.46 (dd, J =
3.03–3.13 (m, 2H), 6.65 (d, J = 1.6 Hz, 1H), 7.72 (d, J = 8.4 Hz, 3.4, 1.8 Hz, 1H), 6.64 (d, J = 3.4 Hz, 1H), 7.44 (d, J = 1.4 Hz, 1H).
2H), 7.77 (d, J = 8.4 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ 13C NMR (101 MHz, CDCl3): δ 14.49, 14.86, 59.91, 111.36,
28.82, 35.44, 123.81 (q, J = 273.4 Hz), 126.03 (q, J = 3.7 Hz), 112.10, 112.61, 142.24, 144.00, 154.52, 167.34.
127.18, 129.52, 132.73 (q, J = 32.8 Hz), 137.50, 171.94, 208.98.
ethyl
(E)-3-(thiophen-2-yl)but-2-enoate.21
Eluent:
3-(furan-2-yl)cyclopent-2-en-1-one 23
.
Eluent: petroleum petroleum ether/EtOAc (200:1 v/v). Yellow oil, yield 48 mg
ether/EtOAc (10:1 v/v). Yellow solid, yield 20 mg (45%). 1H (82%). H NMR (400 MHz, CDCl3): 1.32 (t, J = 7.1 Hz, 2H), 2.61
NMR (400 MHz, CDCl3): δ 2.46–2.61 (m, 2H) , 2.88–3.02 (m, (d, J = 1.0 Hz, 2H), 4.20 (q, J = 7.1 Hz, 1H), 6.22–6.29 (m, 1H),
2H), 6.40 (s, 1H), 6.55 (d, J = 1.6 Hz, 1H), 6.84 (d, J = 2.5 Hz, 7.05 (t, J = 4.4 Hz, 1H), δ 7.32 (d, J = 4.4 Hz, 2H). 13C NMR (101
1H), 7.60 (s, 1H). 13C NMR (101 MHz, CDCl3): δ 27.21, 34.68, MHz, CDCl3): δ14.49, 17.43, 60.01, 114.41, 126.83, 127.19,
1
112.54, 113.73, 124.81, 145.79, 150.59, 161.50, 208.85.
3-(thiophen-2-yl)cyclopent-2-en-1-one.23 Eluent: petroleum
128.06, 145.72, 147.92, 166.90.
ethyl
4'-methoxy-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-
ether/EtOAc (10:1 v/v). White solid, yield 43.8 mg (89%). 1H carboxylate.25 Eluent: petroleum ether/EtOAc (100:1 v/v).
1
NMR (400 MHz, CDCl3) δ 2.49–2.65 (m, 2H), 2.97–3.11 (m, 2H), Colorless oil, yield 60 mg (77%). H NMR (400 MHz, CDCl3): δ
6.36 (s, 1H), 7.14 (dd, J = 4.0, 4.8 Hz, 1H), 7.45 (d, J = 3.6 Hz, 0.91 (t, J = 7.1 Hz, 3H), 1.66–1.80 (m, 4H), 2.32–2.47 (m, 4H),
1H), 7.54 (d, J = 4.8 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 3.80 (s, 3H), 3.91 (q, J = 7.1 Hz, 2H), 6.84 (d, J = 8.7 Hz, 2H),
29.39, 35.13, 125.88, 128.44, 128.61, 130.34, 138.73, 166.71, 7.08 (d, J = 8.7 Hz, 2H). 13C NMR (101 MHz, CDCl3): δ 13.85,
208.61.
22.08, 22.68, 26.90, 32.62, 55.36, 60.16, 113.47, 127.92,
(E)-3-(4-(dimethylamino)phenyl)but-2-enoate.24 128.16, 135.87, 144.82, 158.82, 170.51.
ethyl 4'-methyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-
ethyl
Eluent: petroleum ether/EtOAc (60:1 v/v). White solid, yield 65
1
mg (93%). H NMR (400 MHz, CDCl3): δ 1.31 (t, J = 7.1 Hz, 3H), carboxylate. Eluent: petroleum ether/EtOAc (100:1 v/v). Light
2.57 (s, 3H), 2.99 (s, 6H), 4.20 (q, J = 7.1 Hz, 2H), 6.12 (s, 1H), yellow oil, yield 54.5 mg (74%). 1H NMR (400 MHz, CDCl3): 0.88
6.68 (d, J = 8.9 Hz, 2H), 7.45 (d, J = 8.9 Hz, 2H). 13C NMR (101 (t, J = 7.1 Hz, 3H), 1.66–1.80 (m, 4H), 2.33 (s, 1H), 2.34–2.46
MHz, CDCl3): δ 14.56, 17.32, 40.39, 59.64, 111.83, 112.89, (m, 4H), 3.89 (q, J = 7.1 Hz, 2H), 7.03 (d, J = 7.9 Hz, 2H), δ 7.11
127.54, 129.09, 151.20, 155.45, 167.64.
ethyl
(E)-(4-methoxyphenyl)but-2-enoate.24
(d, J = 8.0 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 13.74, 21.28,
Eluent: 22.09, 22.66, 26.80, 32.70, 60.14, 126.86, 127.92, 128.76,
petroleum ether/EtOAc (200:1 v/v). Colorless oil, yield 54.9 mg 136.71, 140.63, 145.55, 170.30. HR-MS: m/z 245.15282
( 83%). 1H NMR (400 MHz, CDCl3): δ 1.31 (t, J = 7.1 Hz, 3H), 2.56 [M+H]+; calcd for C16H21O2, 245.15361.
(d, J = 1.2 Hz, 3H), 3.83 (s, 3H), 4.20 (q, J = 7.1 Hz, 2H), 6.08–
ethyl
4'-(dimethylamino)-3,4,5,6-tetrahydro-[1,1'-
6 | J. Name., 2012, 00, 1-3
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