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J.W. Barlow et al. / European Journal of Medicinal Chemistry 46 (2011) 1545e1554
136.84, 137.05, 137.16, 137.45 (5ꢃ ArC); HRMS (M þ Na)þ 407.1987,
2.35 (1H, broad s, OH), 3.12e3.46 (6H, m, 2ꢃ CH2 indan and
OCH2CH2O), 4.15 (1H, q, J ¼ 7 Hz, CH), 7.15e7.20 (4H, m, 4ꢃ AreCH),
7.47 (2H, m, 2ꢃ AreCH), 7.56 (1H, m, AreCH), 8.01 (2H, m, 2ꢃ
COAreCH); 13C NMR dC 13.63 (CH3), 39.30, 41.08 (2ꢃ CH2Ar), 45.82
(CH), 61.48, 63.69 (OCH2CH2OH), 87.91 (quat. C), 123.63, 123.72,
126.24 (ꢃ2C), 127.89 (ꢃ2C), 128.17 (ꢃ2C), 132.50 (9ꢃ AreCH),
137.89, 140.60, 140.94 (3ꢃ AreC), 203.00 (C]O); MS, m/z, (RI) 249
(Mþ1, enone, 100), 248 (Mþ, enone, 25), 176 (13), 105 (9); HRMS
(M þ Na)þ 333.1470, C20H22O3Na requires 333.1467.
C27H28O2Na requires 407.1987.
7.3.14. 2-(1,2,3,4-Tetrahydro-2-naphthalenyliden)-1-indanone
(20b)
The title compound, the
described for 3b, by the reaction of 19 [24], prepared as for 2, with 7
[23]. Yield 31%; m.p. 109e110 ꢁC; IR (KBr disc) max/cmꢀ1 1683,
b-elimination product, was obtained as
y
1597, 1462, 1304, 1222 cmꢀ1; 1H NMR (CDCl3, 400 Hz) dH 2.45 (2H,
m, CH2), 3.10 (2H, m, CH2), 3.57 (2H, broad s, CH2CHCO), 3.79 (1H, t,
J ¼ 7 Hz, CH), 6.70 (1H, s, C]CH), 7.21 (1H, dd, J1 ¼ 8.4 Hz, J2 ¼ 7 Hz,
AreCH), 7.28e7.31 (2H, m, 2ꢃ AreCH), 7.35e7.41 (2H, m, 2ꢃ
AreCH), 7.47 (1H, d, J ¼ 7 Hz, AreCH), 7.54 (1H, dd, J1 ¼ 8.4 Hz,
J2 ¼ 7.5 Hz, AreCH), 8.17 (1H, d, J ¼ 8 Hz, COAreCH); 13C NMR dC
27.70, 28.92 (2ꢃ CH2Ar), 39.98 (CH2C]C), 49.60 (CH), 120.14,
123.11, 123.87, 125.86, 126.34, 127.29, 128.32, 128.37, (C]CH and 7ꢃ
AreCH), 132.10 (quat. C), 133.06 (AreCH), 142.97, 143.51, 144.33,
146.07 (4ꢃ quat. C), 197.12 (C]O); MS, m/z, (RI) 261 (Mþ1, 25), 260
(Mþ, 100), 141 (39), 115 (61), 89 (44), 63 (19); HRMS (M þ H)þ,
7.3.18. 2-(1H-2-Indenyl)-2-methyl-1,3-diphenyl-1-propanone (25)
The title compound was obtained by the treatment of 24 with
benzyl bromide as described for 5. Yield 40%, pale oil; IR (film)
y
max/cmꢀ1 3068, 3031, 1681, 1463, 1240, 967, 910 cmꢀ1 1H NMR
;
(CDCl3, 400 Hz) dH 1.51 (3H, s, CH3), 3.21e3.33 (2H, m, CH2), 3.49
(2H, 2ꢃ d, J ¼ 12.5 Hz, CH2), 6.72 (1H, s, C]CH), 6.90e6.93 (2H, m,
2ꢃ AreCH), 7.16e7.47 (10H, m, 10ꢃ AreCH), 7.77e7.93 (2H, m, 2ꢃ
COAreCH); 13C NMR dC 22.8 (CH3), 38.9, 44.4 (2ꢃ CH2), 53.7
(CH3CCH2), 120.5, 123.3, 124.1, 125.9, 126.1, 127.3 (ꢃ2C), 127.8 (ꢃ2C),
128.1 (ꢃ2C), 128.5, 130.2 (ꢃ2C), 131.4 (14ꢃ AreCH and C]CH),
137.0, 137.0, 142.6, 144.0, 150.8 (4ꢃ AreC and C]CH), 202.6 (C]O);
MS, m/z, (RI) 338 (Mþ, 7), 233 (100), 105 (28).
261.1301, C19H17
C19H16ONa requires 283.1099.
O
requires 261.1279; (M
þ
Na)þ, 283.1081,
7.3.15. 2-Benzyl-2-(3,4-dihydro-2-naphthalenyl)-1-indanone (21)
The title compound was obtained by the treatment of 20b with
benzyl bromide as described for 5. Yield 54%; white solid, m.p.
7.3.19. 2-(1H-2-Indenyl)-2-methyl-1,3-diphenyl-1-propanol (26)
The title compound was obtained by the treatment of 25 with
sodium borohydride as described for 6 as a white crystalline solid,
130e132 ꢁC; IR (film) max/cmꢀ1 2929, 1683, 1602, 1455, 1292,
y
1231 cmꢀ1; 1H NMR (CDCl3, 400 Hz) dH 2.23 (1H, m, 1H of CH2CH2),
2.36 and 2.40 (1H, 2ꢃ dd, J1 ¼ 4.5 Hz, J2 ¼ 3.5 Hz, 1H of CH2CH2),
2.81 and 2.85 (1H, 2ꢃ dd, J1 ¼ 5 Hz, J2 w 3 Hz, 1H of CH2CH2), 3.07
(1H, m, 1H of CH2CH2), 3.35 (2H, 2ꢃ d, J ¼ 13.5 Hz, CH2), 3.43 (2H,
2ꢃ d, J ¼ 23 Hz, CH2), 6.54 (1H, s, C]CH), 7.12e7.34 (10H, m, 10ꢃ
AreCH), 7.41e7.45 (2H, m, 2ꢃ AreCH), 8.21 (1H, d, J ¼ 8 Hz,
COAreCH); 13C NMR dC 25.45, 30.89, 38.92, 43.98 (4ꢃ CH2), 52.92
(CH), 120.27, 123.03, 124.07, 125.91, 125.95, 126.12, 127.41 (ꢃ2C),
127.68, 128.13, 129.49, 130.49 (ꢃ2C) (C]CH and 12ꢃ AreCH),
131.92 (quat. C), 132.81 (AreCH), 137.19, 142.63, 143.05, 143.90,
146.50 (5ꢃ quat. C), 198.02 (C]O); MS, m/z, (RI) 351 (Mþ1, 31), 350
(Mþ, 100), 259 (75), 231 (34), 115 (11); HRMS (M þ Na)þ, 373.1547,
C26H22ONa requires 373.1568.
primarily as one pair of isomers: m.p. 74e76 ꢁC; IR (film) max/cmꢀ1
y
3615, 3563, 3066, 3032, 2977,1604,1551,1496,1455,1392,1252,1206,
1044, 1024 cmꢀ1; 1H NMR (CDCl3, 400 Hz) dH 1.05 (3H, s, CH3), 2.08
(1H, broad s, OH), 3.04 (2H, s, CH2), 3.42e3.60 (2H, 2ꢃ d, J ¼ 23 Hz,
CH2), 4.81 (1H, s, CHOH), 6.66 (C]CH), 7.05e7.35 (13H, m, 13ꢃ
AreCH), 7.44e7.46 (1H, d, J ¼ 7.0 Hz, AreCH); 13C NMR dC 18.83 (CH3),
39.93 (CH2), 44.57 (CH2), 46.20 (CCH3), 79.76 (CHOH),120.10,123.00,
123.70, 125.67, 125.79, 127.18 (ꢃ2C), 127.31 (ꢃ2C), 127.67 (ꢃ2C),
128.63,129.61, 130.01 (ꢃ2C) (C]CH and 14ꢃ AreCH),137.68,140.38,
142.94, 144.18, 148.03 (5ꢃ quat. C); MS, m/z, (RI) 145 (11), 144 (100),
115 (44); HRMS (M þ Na)þ 363.1731, C25H24ONa requires 363.1725.
7.3.20. 2-[2-(2-Hydroxyethoxy)-1,2,3,4-tetrahydro-2-
naphthalenyl]-1-phenyl-1-propanone (27)
7.3.16. 2-Benzyl-2-(3,4-dihydro-2-naphthalenyl)-1-indanol (22)
The title compound was obtained by the treatment of 21 with
sodium borohydride as described for 6. Yield 94%; white solid, m.p.
The title compound was obtained as described for 3b, by the
reaction of 23 [25], prepared as for 2, with 7 [23]. Yield 28%; IR (film)
y
max/cmꢀ1 3438, 2938, 2877, 1676, 1449, 1223, 1095, 1051 cmꢀ1; 1H
74e76 ꢁC; IR (film)
y
max/cmꢀ1 3408, 3069, 3029, 2930, 1548, 1454,
NMR (CDCl3, 400 Hz) dH 1.35 and 1.39 (3H, 2ꢃ d, J ¼ 7 Hz, CH3), 1.67
and 2.12 (2H, 2ꢃ m, CH2CH2Ar), 2.44 (1H, 2ꢃ broad s, OH), 2.61e2.76
(2H, m, CH2Ar), 2.90e3.14 (2H, m, CH2Ar), 3.36 and 3.54 (4H, 2ꢃ m,
OCH2CH2OH), 4.15 (1H, m, CH), 7.02e7.14 (4H, m, 4ꢃ AreCH),
7.46e7.51 (2H, m, 2ꢃ AreCH), 7.58 (1H, m, AreCH), 8.00 and 8.03
(2H, 2ꢃ d, J ¼ 7.5 and 7 Hz, 2ꢃCOAreCH);13C NMR dC 12.03and 12.84
(CH3), 25.23 and 25.32 (CH2), 28.95 and 29.07 (CH2), 34.92 and 35.21
(CH2), 44.14 and 45.22 (CH), 61.44 and 61.48 (OCH2), 62.31 and 62.82
(OCH2), 76.42 and 76.76 (CH2CCH2), 125.15 and 125.37 (AreCH),
125.41 and 125.55 (AreCH), 127.81 (ꢃ2C, 2ꢃ AreCH), 127.88 and
127.94 (AreCH), 128.33 (ꢃ2C, 2ꢃ AreCH), 128.70 and 129.01
(AreCH), 132.66 and 132.69 (AreCH), 133.74 and 134.05 (AreC),
135.28 and 135.89 (AreC), 137.98 and 138.08 (AreC), 202.77 and
202.95 (C]O); MS, m/z, (RI) 262 (Mþ enone, 24),157 (100),105 (62);
HRMS (M þ Na)þ 347.1591, C21H24O3Na requires 347.1623.
1379 cmꢀ1; 1H NMR (CDCl3, 400 Hz) dH 1.73 and 2.06 (1H, s and d,
Jd w 7 Hz, OH), 2.43e2.66 (3H, m, 3H of CH2), 2.78e3.28 (1H, broad
m, 5H of CH2), 4.96 and 5.30 (1H, s and d, Jd w 7 Hz, CHOH), 6.16
(1H, s, C]CH), 6.94e7.07 (3H, m, 3ꢃ AreCH), 7.14e7.25 (6H, m, 6ꢃ
AreCH), 7.28e7.55 (m, 4ꢃ AreCH); 13C NMR dC 24.94 and 25.20
(CH2), 27.80 and 27.87 (CH2), 35.94 (ꢃ2) (CH2), 36.94 and 40.23
(CH2), 58.12 and 58.48 (alip.quat. C), 80.99 and 82.23 (CHOH),
123.21, 123.90, 124.26, 124.86, 125.37, 125.62 (ꢃ2C), 125.66, 125.82,
125.97, 126.00, 126.04, 126.09, 126.29, 126.38, 126.50, 126.55,
126.67, 127.25 (ꢃ2C), 127.29 (ꢃ2C), 127.85, 128.61, 129.81 (ꢃ2C),
130.03 (ꢃ2C) (13ꢃ AreCH and C]CH), 134.11, 134.32, 134.54,
137.75, 139.69, 142.16 (6ꢃ quat C); MS, m/z, (RI) 351 (Mþ, 5), 333
(100), 259 (99), 243 (31), 205 (21), 103 (35); HRMS (M þ Na)þ
375.1737, C26H24ONa requires 375.1725.
7.3.17. 2-[2-(2-Hydroxyethoxy)-2,3-dihydro-1H-2-indenyl]-1-
phenyl-1-propanone (24)
7.3.21. 2-(3,4-Dihydro-2-naphthalenyl)-2-methyl-1,3-diphenyl-1-
propanol (29)
The title compound was obtained as described for 3b, by the
reaction of 23[25], prepared as for 2, with 4. Yield 69%; IR (film)
The title compound was obtained by the treatment of 27 with
benzyl bromide as described for 5. The crude reaction mixture was
monitored by GCMS, revealing a mixture of products, including
the desired mass of compound 28: MS, m/z, (RI) 353 (Mþ, 18), 261
y
max/cmꢀ1 3460, 2939, 1737, 1679, 1596, 1448, 1227, 1086,
1057 cmꢀ1; 1H NMR (CDCl3, 400 Hz) dH 1.32 (3H, d, J ¼ 7 Hz, CH3),