Chiral Prolinol-Substituted Chromophores
J. Chin. Chem. Soc., Vol. 51, No. 3, 2004 491
-
1
1
494, 1454, 1274, 1149, 1053, 839, 757 cm ; HRMS m/z
3.85 (m, 10H), 6.00 (d, J = 4.2 Hz, 1H), 7.32 (d, J = 6.6 Hz,
2H), 7.41 (d, J = 4.2 Hz, 1H), 7.82 (d, J = 6.6 Hz, 2H), 8.51 (s,
+
calcd for C22
H
22
N
2
O
3
S
2
(M ): 426.1072, found 426.1074.
: C, 61.95; H, 5.20; N, 6.57.
1
3
Anal. Calcd for C22
H
22
N
2
O
3
S
2
6
1H); C NMR (Acetone-D ) d 22.83, 23.64, 25.22, 27.81,
2
5
Found: C, 61.59; H, 5.17; N, 6.77. [a]D = -105 (c 1.0,
CH Cl ).
32.44, 51.57, 55.67, 59.64, 61.28, 61.32, 64.47, 102.63,
121.34, 124.61, 129.24, 134.67, 137.54, 154.31, 157.12,
2
2
1
61.58; IR (film) 3421, 2921, 1626, 1523, 1478, 1399, 1267,
-
1
(S)-(-)-5-[(2-Hydroxymethyl)pyrrolidinyl]-2-furaldehyde-
30 2 4 2
1141, 1023, 872, 748 cm ; HRMS m/z calcd for C22H N O S
+
25
4
-(phenylsulfonyl)phenylimine (8b)
D
2 2
(M ): 450.1647, found 450.1639. [a] = -87 (c 1.0, CH Cl ).
1
(
6
763 mg, 93%): mp 124 °C. H NMR (Acetone-D ) d
2
1
.03-2.10 (m, 4H), 3.40 (m, 1H), 3.52-3.66 (m, 4H), 3.99 (m,
(S)-(-)-5-[(2-Hydroxymethyl)pyrrolidinyl]-2-thiophene-
H), 5.34 (d, J = 3.8 Hz, 1H), 7.12 (d, J = 3.8 Hz, 1H), 7.26 (d,
carbaldehyde-4-[(6-hydroxyhexyl)sulfonyl]phenylimine
J = 8.6 Hz, 2H), 7.57-7.65 (m, 3H), 7.89 (d, J = 8.6 Hz, 2H),
(10b)
1
3
1
8
2
1
1
1
C
.00 (d, J = 8.2 Hz, 3H); C NMR (Acetone-D
6
) d 23.50,
(712 mg, 82%): mp 78 °C. H NMR (Acetone-D
6
) d
8.05, 48.58, 61.32, 62.55, 85.97, 121.52, 127.30, 128.95,
29.43, 133.00, 136.45, 142.87, 143.01, 146.29, 157.73,
61.40; IR (film) 3300, 3089, 1679, 1617, 1589, 1446, 1298,
1.32-1.50 (m, 6H), 1.44 (m, 2H), 2.04-2.15 (m, 4H), 3.13-
4.00 (m, 10H), 5.35 (d, J = 3.8 Hz, 1H), 7.15 (d, J = 3.8 Hz,
1H), 7.31 (d, J = 8.5 Hz, 2H), 7.82 (d, J = 8.5 Hz, 2H), 8.05 (s,
-
1
13
271, 1152, 1105, 1024, 850, 731 cm ; HRMS m/z calcd for
1H); C NMR (Acetone-D
6
) d 23.49, 24.19, 25.89, 28.48,
+
25
D
22
H
22
N
2
O
4
S (M ): 410.1300, found 410.1296. [a] = -73 (c
28.85, 33.10, 49.25, 56.38, 62.01, 62.04, 63.36, 86.58,
121.93, 129.91, 135.18, 143.67, 147.01, 158.39, 162.08;. IR
1
2 2
.0, CH Cl ).
(
film) 3434, 2944, 1629, 1545, 1401, 1282, 1136, 1031, 916,
-
1
+
(S)-(-)-5-[(2-Hydroxymethyl)pyrrolidinyl]-2-thiophenecar-
867 cm ; HRMS m/z calcd for C22
H
30
N
2
O
5
S (M ): 434.1875,
2
5
baldehyde-4-[(2-hydroxyethyl)sulfonyl]phenylimine (9a)
found 434.1842. [a] = -64 (c 1.0, CH
2
Cl
2
).
D
1
(
6
726 mg, 92%): mp 115 °C. H NMR (Acetone-D ) d
2
1
.14-2.17 (m, 4H), 3.29-4.09 (m, 11H), 6.00 (d, J = 3.1 Hz,
H), 7.32 (d, J = 6.4 Hz, 2H), 7.40 (d, J = 3.1 Hz, 1H), 7.85 (d,
(S)-(-)-5-(Methylsulfonyl)-2-thiophenecarbaldehyde-4-[(2-
hydroxymethyl)pyrrolidinyl]phenylimine (16a)
1
3
1
J = 6.4 Hz, 2H), 8.50 (s, 1H); C NMR (Acetone-D
6
) d 23.57,
8.33, 51.51, 55.83, 58.29, 61.23, 64.40, 102.62, 121.22,
24.49, 129.18, 135.03, 137.54, 154.22, 157.09, 161.57; IR
(685 mg, 94%): mp 114 °C. H NMR (Acetone-D
6
) d
2
1
1.99-2.14 (m, 4H), 3.18 (m, 1H), 3.28 (s, 3H), 3.42 (m, 2H),
3.66 (m, 1H), 3.84 (m, 1H), 6.67 (d, J = 6.7 Hz, 2H), 7.31 (d, J
(
film) 3436, 3248, 2923, 1602, 1567, 1446, 1280, 1136, 1033,
= 6.7 Hz, 2H), 7.34 (d, J = 3.0 Hz, 1H), 7.71 (d, J = 3.0 Hz,
-
1
+
13
8
3
47, 736 cm ; HRMS m/z calcd for C18
H
22
N
2
O
4
S
2
(M ):
).
6
1H), 8.81 (s, 1H); C NMR (Acetone-D ) d 22.96, 28.11,
2
5
94.1021, found 394.1034. [a] = -105 (c 1.0, CH
2
Cl
2
45.01, 48.47, 60.54, 61.72, 112.18, 123.17, 129.48, 133.45,
37.87, 143.23, 145.50, 147.74, 151.55; IR (film) 3543,
2929, 1610, 1559, 1508, 1290, 1130, 1039, 1010, 965, 820,
D
1
(
S)-(-)-5-[(2-Hydroxymethyl)pyrrolidinyl]-2-furaldehyde-
-
1
+
4
-[(2-hydroxyethyl)sulfonyl]phenylimine (9b)
765 cm ; HRMS m/z calcd for C17
found 364.0911. Anal. Calcd for C17
5.53; N, 7.69. Found: C, 56.02; H, 5.67; N, 7.51. [a]D = -134
(c 1.0, CH Cl ).
H
20
N
2
O
3
S
2
(M ): 364.0915,
1
(
643 mg, 86%): mp 106 °C. H NMR (Acetone-D
6
) d
H N O S : C, 56.02; H,
20 2 3 2
25
2
7
8
2
1
3
7
.04-2.17 (4m), 3.37-3.89 (m, 11H), 5.36 (d, J = 3.8 Hz, 1H),
.16 (d, J = 3.8 Hz, 1H), 7.30 (d, J = 8.6 Hz, 1H), 7.83 (d, J =
2
2
1
3
6
.6 Hz, 2H), 8.05 (s, 1H); C NMR (Acetone-D ) d 23.44,
8.07, 48.59, 55.87, 58.37, 61.37, 62.63, 85.92, 121.20,
29.27, 134.95, 143.01, 146.32, 157.81, 161.43; IR (film)
275, 2920, 1627, 1534, 1477, 1400, 1267, 1134,1025, 872,
(S)-(-)-5-(Methylsulfonyl)-2-furaldehyde-4-[(2-hydroxy-
methyl)pyrrolidinyl]phenylimine (16b)
1
(750 mg, 88%): mp 105 °C. H NMR (Acetone-D
6
) d
-
1
+
35 cm ; HRMS m/z calcd for C18
H
22
N
2
O
5
S (M ): 378.1249,
).
1.99-2.16 (m, 4H), 3.14 (m, 1H), 3.29 (s, 4H), 3.46 (m, 2H),
2
5
found 378.1260. [a] = -72 (c 1.0, CH
2
Cl
2
3.65 (m, 1H), 3.86 (m, 1H), 6.70 (d, J = 6.7 Hz, 2H), 7.09 (d, J
D
=
2.8 Hz, 1H), 7.28 (d, J = 2.8 Hz, 1H), 7.32 (d, J = 6.7 Hz,
1
3
(
S)-(-)-5-[(2-Hydroxymethyl)pyrrolidinyl]-2-thiophene-
carbaldehyde-4-[(6-hydroxyhexyl)sulfonyl]phenylimine
10a)
6
2H), 8.53 (s, 1H); C NMR (Acetone-D ) d 22.75, 27.92,
42.64, 48.24, 60.44, 61.48, 112.05, 112.62, 118.10, 122.92,
138.05, 140.45, 147.66, 150.34, 156.82; IR (film) 3363,
(
1
-1
(
793 mg, 88%): mp 86 °C. H NMR (Acetone-D
6
) d
1610, 1522, 1507, 1308, 1153, 1097, 1026, 817, 750 cm ;
+
1
.38-1.46 (m, 6H), 1.66 (m, 2H), 2.04-2.17 (m, 4H), 3.14-
HRMS m/z calcd for C17
H
20
N
2
O
4
S (M ): 348.1144, found