MedChemComm
DOI: 10.1039/C5MD00139K
ARTICLE
Journal Name
(s, 1H), 4.02 (s, 3H), 3.98 (s, 3H), 3.96 (s, 3H), 3.93 (s, 3H), (E)-4,5,6-trimethoxy-2-(2,3,4-trimethoxybenzylidene)-2,3-
3.91 (d, J = 1.6 Hz, 2H). 13C-NMR (101 MHz, CDCl3) δ 193.45, dihydro-1H-inden-1-one(5f)
154.41, 149.80, 148.09, 147.50, 145.81, 136.01, 133.65, 133.55,
Light yellow solid, yield: 78.4%. mp: 156.5-158.8 oC, 1H-
132.89, 128.95, 124.84, 115.77, 110.77, 101.54, 61.12, 60.76,
NMR (400 MHz, CDCl3) δ 7.95 (t, J = 1.9 Hz, 1H), 7.48 (d, J =
8.9 Hz, 1H), 7.20 (s, 1H), 6.79 (d, J = 8.8 Hz, 1H), 4.01 (s, 3H),
56.27, 55.98, 29.14.HRMS (ESI) (m/z) [M+Na]+ calcd for
C20H20O6, 379.1152; found, 379.1145. Purity: 97.3% (by
3.97 (s, 3H), 3.96 (s, 3H), 3.93 (d, J = 0.7 Hz, 6H), 3.90 (s, 3H),
HPLC).
3.87 (d, J = 2.0 Hz, 2H).13C-NMR (101 MHz, CDCl3) δ 193.20,
155.25, 154.40, 149.77, 147.38, 142.51, 135.86, 133.87, 133.56,
127.77, 124.78, 122.60, 107.44, 101.62, 61.86, 61.13, 60.93,
60.77, 56.31, 56.08, 29.20. HRMS (ESI) (m/z) [M+Na]+ calcd
for C22H24O7, 423.1414; found, 423.1397. Purity: 97.2% (by
HPLC).
(E)-4,5,6-trimethoxy-2-(4-methoxy-3-nitrobenzylidene)-2,3-
dihydro-1H-inden-1-one(5b)
1
Beige solid, yield: 76.2%. mp: 225.6-227.8 oC, H NMR (400
MHz, CDCl3) δ 8.17 (d, J = 2.2 Hz, 1H), 7.83 (dd, J = 8.8, 2.2
Hz, 1H), 7.53 (t, J = 1.9 Hz, 1H), 7.19 (t, J = 4.4 Hz, 2H), 4.03
(s, 6H), 3.99 (s, 3H), 3.93 (s, 3H), 3.91 (d, J = 1.9 Hz, 2H).13C (E)-2-(3-fluoro-4-methoxybenzylidene)-4,5,6-trimethoxy-2,3-
NMR (101 MHz, CDCl3) δ 192.79, 154.68, 153.37, 149.80, dihydro-1H-inden-1-one(5g)
147.84, 142.06, 139.97, 136.29, 135.78, 135.17,130.39, 128.11,
126.89, 113.90, 101.56, 61.15, 60.82, 56.75, 56.31,
28.81.HRMS (ESI) (m/z) [M+Na]+ calcd for C20H19NO7,
408.1054; found, 408.1036. Purity: 97.5% (by HPLC).
o
1
Buff solid, yield: 86.1%. mp:178.2-179.6 C, H-NMR (400
MHz, CDCl3) δ 7.52 (s, 1H), 7.46 (dd, J = 12.4, 2.0 Hz, 1H),
7.41 (d, J = 8.8 Hz, 1H), 7.18 (s, 1H), 7.04 (t, J = 8.6 Hz, 1H),
4.03 (s, 3H), 3.98 (s, 3H), 3.95 (s, 3H), 3.93 (s, 3H), 3.89 (d, J =
1.8 Hz, 2H).13C-NMR (101 MHz, CDCl3) δ 193.14 , 154.51,
153.48, 151.03, 149.76, 148.90 (d, J = 11.0 Hz), 147.60 ,
135.82, 133.52 (d, J = 14.0 Hz), 132.17, 128.57 (d, J = 6.6 Hz),
128.12 (d, J = 2.9 Hz,), 117.28 (d, J = 18.7 Hz), 113.30, 101.52,
61.12, 60.78, 56.26, 56.22, 28.95.HRMS (ESI) (m/z) [M+H]+
calcd for C20H19FO5, 358.3655; found, 358.3657. Purity: 99.7%
(by HPLC).
(E)-4,5,6-trimethoxy-2-(4-methoxybenzylidene)-2,3-dihydro-1H-
inden-1-one(5c)
1
Yellow solid, yield: 83.4%. mp: 141.5-143.7 oC, HNMR (400
MHz, CDCl3) δ 7.66 (d, J = 8.7 Hz, 2H), 7.59 (s, 1H), 7.19 (s,
1H), 6.99 (d, J = 8.8 Hz, 2H), 4.03 (s, 3H), 3.98 (s, 3H), 3.93 (s,
3H), 3.91 (d, J = 1.5 Hz, 2H), 3.87 (s, 3H).13C-NMR (101 MHz,
CDCl3) δ 193.33, 160.80, 154.41, 149.78, 147.39, 135.81,
133.74, 133.31, 132.51, 132.40, 128.12, 114.45, 101.52, 61.11, (E)-2-(3-bromo-4-methoxybenzylidene)-4,5,6-trimethoxy-2,3-
60.75, 56.26, 55.36, 29.69, 29.14. HRMS (ESI) (m/z) [M+Na]+, dihydro-1H-inden-1-one(5h)
calcd. for C20H20O5, 363.1203; found, 363.1191. Purity: 97.1%
(by HPLC).
o
1
Bluish yellow, yield: 82.9%. mp: 208.5-210.1 C. H-NMR
(400 MHz, CDCl3) δ 7.88 (s, 1H), 7.61 (d, J = 8.5 Hz, 1H), 7.50
(s, 1H), 7.18 (s, 1H), 6.98 (d, J = 8.5 Hz, 1H), 4.04 (s, 3H), 3.98
(s, 3H), 3.96 (s, 3H), 3.93 (s, 3H), 3.89 (s, 2H). 13C NMR (101
MHz, CDCl3) δ 193.02, 156.81, 154.50, 149.77, 147.58, 135.78,
135.14, 133.60, 133.46, 131.69, 131.55, 129.42, 112.27, 111.93,
101.51, 61.12, 60.81, 56.35, 56.27, 28.90.HRMS (ESI) (m/z)
[M+H]+ calcd for C20H19BrO5, 419.0489; found, 419.0472.
Purity: 97.7% (by HPLC).
(E)-2-(3,4-dimethoxybenzylidene)-4,5,6-trimethoxy-2,3-dihydro-
1H-inden-1-one (5d)
o
1
Primrose solid, yield: 83.8%; mp: 178.7-180.9 C, H NMR
(400 MHz, CDCl3) δ 7.58 (s, 1H), 7.34 (d, J = 8.3 Hz, 1H), 7.19
(s,1H), 7.18(s,1H) 6.97 (d, J = 8.4 Hz, 1H), 4.02 (s, 3H), 3.98 (s,
3H), 3.96 (s, 3H), 3.95 (s, 3H), 3.93 (s, 3H), 3.92 (s, 2H). 13C-
NMR (101 MHz, CDCl3) δ 193.27, 154.43, 150.53, 149.75,
149.03, 147.40, 135.73, 133.69, 133.60, 132.67, 128.38, 124.29, (E)-2-(3-amino-4-methoxybenzylidene)-5,6,7-trimethoxy-2,3-
113.76, 111.29, 101.50, 61.13, 60.77, 56.27, 55.99, 55.97, dihydro-1H-inden-1-one (5i)
29.03. HRMS (ESI) (m/z) [M+H]+, calcd. for C21H22O6,
370.1489; found, 371.1468. Purity: 96.3% (by HPLC).
To a solution of 5b (2 mmol) in ethanol (10 mL) and water (3
mL), iron powder (6.7 mmol) and NH4Cl (1.2 mmol) were
added. After stirred at 85 oC for 4h, the mixture was filtered and
then evaporated in vacuum. The residue was dissolved in ethyl
acetate, washed with water , dried over Na2SO4, filtered, and
concentrated to give the crude product which was purified by
recrystallization from petroleum/ethyl acetate,1/1, to provided
6d. Yellow solid, yield: 79.6%. mp: 168.3.5-170.7 oC. 1H-NMR
(400 MHz, CDCl3) δ 7.44 (t, J = 1.8 Hz, 1H), 7.04 (dd, J = 8.3,
2.0 Hz, 1H), 7.00 (d, J = 2.0 Hz, 1H), 6.83 (d, J = 8.3 Hz, 1H),
6.75 (s, 1H), 4.10 (s, 3H), 3.95 (s, 3H), 3.89 (s, 3H),3.88(s,2H)
3.88 (s, 3H). 13C-NMR (101 MHz, CDCl3) δ 191.10, 159.37,
152.35, 148.54, 147.60, 141.05, 136.44, 132.94, 132.55, 128.65,
124.31, 122.36, 116.29, 110.33, 103.55, 62.18, 61.48, 56.30,
(E)-4,5,6-trimethoxy-2-(3,4,5-trimethoxybenzylidene)-2,3-
dihydro-1H-inden-1-one(5e)
Pale yellow solid, yield: 77.3%. mp: 182.4-184.9 oC, 1H-NMR
(400 MHz, CDCl3) δ 7.55 (s, 1H), 7.20 (s, 1H), 6.92 (s, 2H),
4.03 (s, 3H), 3.98 (s, 3H), 3.95 (s, 6H), 3.94 (s, 3H),
3.93(dd,2H), 3.92 (s, 3H).13C-NMR (101 MHz, CDCl3) δ
193.09, 154.51, 153.36, 149.73, 147.54, 139.82, 135.74, 133.81,
133.62, 133.50, 130.85, 108.20, 101.52, 61.09, 60.95, 60.73,
56.28, 56.25, 28.81. HRMS (ESI) (m/z) [M+Na]+ calcd for
C22H24O7, 423.1414; found, 423.1400. Purity: 96.4% (by
HPLC).
6 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 2012