K. Kato et al.
FULL PAPERS
(2E)-5-Hydroxy-3-methoxy-5-phenyl-2-pentenoic Acid Methyl Ester (2 f)
5,6-Dihydro-6-(furan-2-yl)-4-methoxy-2H-pyran-2-one (3j)
Colorless oil; 1H NMR (CDCl3): d=2.91 (1H, dd, J=3.6, 13.6 Hz), 3.32
(1H, dd J=9.6, 13.6 Hz), 3.65 (3H, s), 3.71 (3H, s), 3.74 (1H, br-s), 4.96–
4.99 (1H, m), 5.18 (1H, s), 7.24–7.44 ppm (5H, m); 13C NMR (CDCl3):
d=42.4, 51.3, 55.8, 72.9, 92.6, 125.5 (2C), 127.4, 128.3 (2C), 144.5, 169.6,
173.3 ppm; IR (neat): n˜ =3431, 2947, 1706, 1616, 1133 cmꢀ1; HRMS-EI:
m/z: [M+] calcd for C13H16O4: 236.1049; found: 236.1048.
Spectral data were identical with those reported in the literature.[1k]
(2E)-5-(Furan-3-yl)-5-hydroxy-3-methoxy-2-pentenoic Acid Methyl Ester
(2k)
Yellow oil; 1H NMR (CDCl3): d=2.95 (1H, dd, J=3.7, 13.7 Hz), 3.35
(1H, dd, J=9.2, 13.7 Hz), 3.44 (1H, br-s), 3.66 (3H, s), 3.69 (3H, s), 4.95
(1H, dd, J=3.7, 9.2 Hz), 5.18 (1H, s), 6.44 (1H, s), 7.37 (1H, t, J=
1.2 Hz), 7.42 ppm (1H, d, J=1.2 Hz); 13C NMR (CDCl3): d=40.8, 51.3,
55.7, 65.9, 92.7, 108.6, 129.1, 138.9, 143.2, 169.4, 173.0 ppm; IR (neat): n˜ =
5,6-Dihydro-4-methoxy-6-phenyl-2H-pyran-2-one (3 f)
Spectral data were identical with those reported in the literature.[1j]
3434, 2949, 1705, 1618, 1134 cmꢀ1
;
HRMS-EI: m/z: [M+] calcd for
(2E)-5-Hydroxy-3-methoxy-5-(4-mthoxyphenyl)-2-pentenoic Acid Methyl
Ester (2g)
C11H14O5: 226.0841; found: 226.0850.
5,6-Dihydro-6-(furan-3-yl)-4-methoxy-2H-pyran-2-one (3k)
Colorless oil; 1H NMR (CDCl3): d=2.89 (1H, dd, J=3.5, 13.6 Hz), 3.30
(1H, dd, J=9.7, 13.6 Hz), 3.65 (3H, s), 3.71 (3H, s), 3.80 (3H, s), 4.93
(1H, dd, J=3.5, 9.7 Hz), 5.17 (1H, s), 6.86–6.89 (2H, m), 7.33–7.36 ppm
(2H, m); 13C NMR (CDCl3): d=42.3, 51.2, 55.2, 55.7, 72.4, 92.4, 113.7
(2C), 126.7 (2C), 136.6, 158.8, 169.5, 173.3 ppm; IR (neat): n˜ =3436, 2948,
Colorless needles; m.p.: 124–1258C; 1H NMR (CDCl3): d=2.62 (1H,
ddd, J=0.6, 4.1, 17.0 Hz), 2.81 (1H, dd, J=11.2, 17.0 Hz), 3.78 (3H, s),
5.21 (1H, s), 5.42 (1H, dd, J=4.1, 11.2 Hz), 6.46–6.46 (1H, m), 7.42–7.43
(1H, m), 7.50 ppm (1H, dd, J=1.0, 1.4 Hz); 13C NMR (CDCl3): d=33.6,
56.2, 70.5, 90.6, 108.6, 123.7, 139.9, 143.7, 166.7, 172.4 ppm; IR (KBr): n˜ =
1707, 1611, 1133 cmꢀ1
;
HRMS-EI: m/z: [M+] calcd for C14H18O5:
3119, 2952, 1680, 1620, 1076 cmꢀ1
;
HRMS-EI: m/z: [M+] calcd for
266.1154; found: 266.1157.
C10H10O4: 194.0579; found: 194.0573.
5,6-Dihydro-4-methoxy-6-(4-methoxyphenyl)-2H-pyran-2-one (3g)
(2E)-3,5-Dimethoxy-7-phenyl-2-heptenoic Acid Methyl Ester (2l)
Colorless needles; m.p.: 98–1008C; 1H NMR (CDCl3): d=2.55 (1H, dd,
J=3.8, 17.1 Hz), 2.83 (1H. ddd, J=1.4, 12.3, 17.1 Hz), 3.78 (3H, s), 3.81
(3H, s), 5.23 (1H, d, J=1.4 Hz), 5.37 (1H, dd, J=3.8, 12.3 Hz), 6.89–6.93
(2H, m), 7.32–7.35 ppm (2H, m); 13C NMR (CDCl3): d=34.9, 55.3, 56.1,
77.0, 90.5, 114.0 (2C), 127.5 (2C), 130.3, 159.8, 167.0, 172.7 ppm; IR
(KBr): 3053, 2961, 2837, 1712, 1626 cmꢀ1; HRMS-EI: m/z: [M+] calcd for
C13H14O4: 234.0892; found: 234.0896.
Colorless oil; 1H NMR (CDCl3): d=1.78–1.83 (2H, m), 2.59–2.66 (1H,
m), 2.77–2.82 (1H, m), 2.87 (1H, dd, J=6.4, 13.2 Hz), 3.16 (1H, dd, J=
6.4, 13.2 Hz), 3.39 (3H, s), 3.55 (1H, quintet, J=6.4 Hz), 3.62 (3H, s),
3.67 (3H, s), 5.06 (1H, s), 7.17–7.29 ppm (5H, m); 13C NMR (CDCl3):
d=31.5, 36.0, 36.4, 50.8, 55.5, 56.8, 78.8, 91.6, 125.7, 128.3 (2C), 128.4
(2C), 142.5, 167.8, 173.8 ppm; IR (neat): n˜ =2943, 1710, 1619, 1133,
1051 cmꢀ1; HRMS-EI: m/z: [M+] calcd for C16H22O4: 278.1518; found:
278.1516.
(2E)-5-(4-Chlorophenyl)-5-hydroxy-3-methoxy-2-pentenoic Acid Methyl
Ester (2h)
(2E)-5-Acetoxy-3-methoxy-7-phenyl-2-heptenoic Acid Methyl Ester (2m)
Colorless oil; 1H NMR (CDCl3): d=2.91 (1H, dd, J=3.6, 13.6 Hz), 3.23
(1H, dd, J=9.4, 13.6 Hz), 3.64 (3H, s), 3.71 (3H, s), 3.91 (1H, d, J=
3.6 Hz), 4.95 (1H, d, J=9.4 Hz), 5.18 (1H, s), 7.29–7.37 ppm (4H, m);
13C NMR (CDCl3): d=42.3, 51.4, 55.8, 72.3, 92.7, 127.0 (2C), 128.4 (2C),
132.9, 142.9, 169.7, 172.9 ppm; IR (neat): n˜ =3415, 2947, 1705, 1617,
1134 cmꢀ1; HRMS-EI: m/z: [M+] calcd for C13H15O4Cl: 270.0659; found:
270.0657.
Colorless oil; 1H NMR (CDCl3): d=1.88–1.94 (2H, m), 1.99 (3H, s),
2.59–2.74 (2H, m), 3.06 (1H, dd, J=8.0, 13.9 Hz), 3.13 (1H, dd, J=5.0,
13.9 Hz), 3.59 (3H, s), 3.68 (3H, s), 5.06 (1H, s), 5.21–5.27 (1H, m), 7.15–
7.29 ppm (5H, m); 13C NMR (CDCl3): d=21.1, 31.7, 35.9, 36.4, 50.9, 55.5,
71.9, 92.2, 125.9, 128.4 (2C), 128.4 (2C), 141.6, 167.8, 170.6, 172.2 ppm; IR
(neat): n˜ =2947, 1737, 1712, 1624, 1134 cmꢀ1; HRMS-EI: m/z: [M+] calcd
for C17H22O5: 306.1467; found: 306.1461.
6-(4-Chlorophenyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one (3h)
(2E)-3-Methoxy-5-(methoxymethoxy)-7-phenyl-2-heptenoic Acid Methyl
Ester (2n)
Spectral data were identical with those reported in the literature.[1k]
Colorless oil; 1H NMR (CDCl3): d=1.82–1.88 (2H, m), 2.61–2.69 (1H,
m), 2.79–2.86 (1H, m), 2.98 (1H, dd, J=6.5, 13.2 Hz), 3.14 (1H, dd, J=
6.5, 13.2 Hz), 3.39 (3H, s), 3.61 (3H, s), 3.67 (3H, s), 3.96 (1H, quintet,
J=6.5 Hz), 4.65 (1H, d, J=7.0 Hz), 4.73 (1H, d, J=7.0 Hz), 5.07 (1H, s),
7.15–7.29 ppm (5H, m); 13C NMR (CDCl3): d=31.6, 36.7, 37.3, 50.9, 55.5,
55.7, 75.7, 91.8, 95.6, 125.7, 128.3 (2C), 128.4 (2C), 142.4, 167.8,
173.4 ppm; IR (neat): n˜ =2946, 1711, 1620, 1134, 1028 cmꢀ1; HRMS-EI:
m/z: [M+] calcd for C17H24O5: 308.1624; found: 308.1618.
(2E)-5-Hydroxy-3-methoxy-5-(naphthalen-2-yl)-2-pentenoic Acid Methyl
Ester (2i)
Colorless oil; 1H NMR (CDCl3): d=3.00 (1H, dd, J=3.4, 13.7 Hz), 3.40
(1H, dd, J=9.6, 13.7 Hz), 3.66 (3H, s), 3.73 (3H, s), 3.92 (1H, d, J=
5.6 Hz), 5.14–5.16 (1H, m), 5.21 (1H, s), 7.44–7.47 (2H, m), 7.55 (1H, dd,
J=1.6, 8.4 Hz), 7.81–7.85 (3H, m), 7.89 ppm (1H, s); 13C NMR (CDCl3):
d=42.4, 51.4, 55.8, 73.1, 92.7, 123.9, 124.1, 125.7, 126.0, 127.7, 128.0,
128.1, 132.9, 133.3, 141.9, 169.8, 173.2 ppm; IR (neat): n˜ =3415, 2946,
1704, 1616, 1133 cmꢀ1
;
HRMS-EI: m/z: [M+] calcd for C17H18O4:
(2E)-5-(tert-Butyldimethylsilyloxy)-3-methoxy-7-phenyl-2-heptenoic Acid
Methyl Ester (2o)
286.1205; found: 286.1210.
Colorless oil; 1H NMR (CDCl3): d=0.02 (3H, s), 0.05 (3H, s), 0.89 (9H,
s), 1.75–1.81 (2H, m), 2.61–2.79 (2H, m), 2.97 (1H, dd, J=6.0, 13.1 Hz),
3.03 (1H, dd, J=7.4, 13.1 Hz), 3.60 (3H, s), 3.67 (3H, s), 4.08–4.14 (1H,
m), 5.04 (1H, s), 7.14–7.28 ppm (5H, m); 13C NMR (CDCl3): d=ꢀ4.67,
ꢀ4.58, 18.0, 25.8, 31.2, 39.4, 39.5, 50.8, 55.3, 70.3, 91.7, 125.6, 128.3 (2C),
128.4 (2C), 142.8, 167.8, 173.8 ppm; IR (neat): n˜ =2950, 2856, 1713, 1621,
1134 cmꢀ1; HRMS-EI: m/z: [M+] calcd for C21H34O4Si: 378.2226; found:
378.2230.
5,6-Dihydro-4-methoxy-6-(naphthalen-2-yl)-2H-pyran-2-one (3i)
Spectral data were identical with those reported in the literature.[1l]
(2E)-5-(Furan-2-yl)-5-hydroxy-3-methoxy-2-pentenoic Acid Methyl Ester
(2j)
Yellow oil; 1H NMR (CDCl3): d=2.97 (1H, dd, J=3.9, 13.7 Hz), 3.53
(1H, dd, J=9.8, 13.7 Hz), 3.66 (3H, s), 3.70 (3H, s), 4.97 (1H, dd, J=3.9,
9.8 Hz), 5.20 (1H, s), 6.28 (1H, dt, J=0.8, 3.2 Hz), 6.32 (1H, dd, J=2.0,
3.2 Hz), 7.37 ppm (1H, dd, J=0.8, 2.0 Hz); 13C NMR (CDCl3): d=38.8,
51.3, 55.8, 66.5, 92.9, 105.6, 110.1, 141.9, 156.4, 169.5, 172.5 ppm; IR
(neat): n˜ =3429, 2949, 1706, 1619, 1133 cmꢀ1; HRMS-EI: m/z: [M+] calcd
for C11H14O5: 226.0841; found: 226.0837.
4-Methoxy-5-(phenylethyl)furan-2ACTHUNRTGNEUNG(5H)-one (3p)
Colorless needles; m.p.: 358C; 1H NMR (CDCl3): d=1.87–1.96 (1H, m),
2.15–2.24 (1H, m), 2.72–2.84 (2H, m), 3.83 (3H, s), 4.74 (1H, dd, J=3.6,
8.4 Hz), 5.05 (1H, d, J=0.8 Hz) 7.18–7.31 ppm (5H, m); 13C NMR
2226
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Chem. Asian J. 2010, 5, 2221 – 2230