10.1002/ejoc.201901362
European Journal of Organic Chemistry
FULL PAPER
147.2, 133.6, 131.5, 130.7, 130.0, 129.1, 128.1, 127.8, 127.4, 126.5,
125.9, 125.7, 124.6, 123.5, 122.6, 122.5, 119.8, 119.5, 115.8, 64.8, 64.7,
64.3, 64.3, 15.8, 15.8, 15.4, 15.4; 31P NMR (202 MHz, CDCl3, ppm): δ -
5.1; IR vmax cm-1:3230, 2979, 2929, 2374, 1620, 1595, 1474, 1253, 1222,
1144, 1032, 1000, 869, 818, 748, 623; MS (ESI) m/z = 423 (M+H)+; ESI-
HRMS) calculated for C24H24O5P (M+H)+: 423.13559, found: 423.13497.
White solid; M.p. 57-60 °C, 240 mg (43%); 1H NMR δ (500 MHz, CDCl3):
7.99 (d, J = 9.0 Hz, 2H), 7.91 (d, J = 8.2 Hz, 2H), 7.79 (d, J = 9.0 Hz, 2H),
7.44 (t, J = 7.9 Hz, 2H), 7.27-7.34 (m, 4H), 3.65-3.77 (m, 4H), 3.46-3.52
(m, 4H), 1.06 (t, J = 7.0 Hz, 6H), 0.84 (t, J= 7.0 Hz, 6H); 13C NMR δ (75
MHz, CDCl3): 146.6 (d, J = 5.4 Hz),133.4, 130.7, 129.9, 127.8, 126.9,
126.1, 125.3, 121.5 (d, J = 8.1 Hz), 119.1, 64.3 (d, J = 6.3 Hz), 64.0 (d, J
= 6.3 Hz), 15.7 (d, J = 6.3 Hz), 15.3 (d, J = 6.3 Hz); 31P NMR (202 MHz,
CDCl3, ppm): δ -7.5; IR vmax cm-1: 2983, 2922, 2377, 1623, 1592, 1507,
1474, 1362, 1278, 1226, 1164, 1100, 1027, 997, 845, 815, 751, 700, 583,
520; MS (ESI) m/z = 559 (M+H)+; (ESI-HRMS) calculated for C28H33O8P2
(M+H)+: 559.16452, found: 559.16349.
rac-[1,1'-binaphthalene]-2,2'-diyl tetraethyl bis(phosphate) (5fa):
white solid; M.p. 142-147 °C, 224 mg (40%); 1H NMR δ (500 MHz,
CDCl3): 7.98 (d, J = 9.0 Hz, 2H), 7.91 (d, J = 8.2 Hz, 2H), 7.80 (d, J = 9.0
Hz, 2H), 7.44 (t, J = 8.0 Hz, 2H), 7.27-7.33 (m, 4H), 3.67-3.76 (m, 4H),
3.46-3.52 (m, 4H), 1.06 (t, J = 7.0 Hz, 6H), 0.84 (t, J= 7.0 Hz, 6H); 13C
NMR δ (75 MHz, CDCl3): 146.6 (d, J = 6.358 Hz),133.4, 130.7, 129.9,
127.8, 126.9, 126.1, 125.3, 121.5 (d, J = 8.1 Hz), 119.1, 64.3 (d, J = 6.3
Hz), 64.0 (d, J = 6.3 Hz), 15.7 (d, J = 6.3 Hz), 15.5 (d, J = 6.3 Hz); 31P
NMR (202 MHz, CDCl3, ppm): δ -7.5; IR vmax cm-1:2980, 2922, 2378,
1624, 1592, 1508, 1475, 1362, 1278, 1226, 1164, 1100, 1028, 997, 845,
Diethyl 2-oxo-2H-chromen-7-yl phosphate (6a):
°
1
White solid; M.p. 62-65 C, 148 mg (49%); H NMR δ (500 MHz, CDCl3):
7.70 (d, J = 9.4 Hz, 1H), 7.48 (d, J = 9.2 Hz, 1H), 7.21 (d, J = 7.3 Hz, 2H),
6.39 (d, J = 9.6 Hz, 1H), 4.21-4.31 (m, 4H), 1.38 (t, J = 7.1 Hz, 6H); 13C
NMR δ (75 MHz, CDCl3): 160.2, 154.8, 153.2 (d, J = 6.3 Hz), 142.7,
128.9, 1116.7 (d, J = 4.5 Hz), 115.9, 115.6, 108.5 (d, J = 5.4 Hz), 64.9- (d,
J = 6.3 Hz), 16.0 (d, J = 6.3 Hz); 31P NMR (202 MHz, CDCl3, ppm): δ -
6.8; IR vmax cm-1:3566, 2984, 2915, 2377, 1737, 1614, 1564, 1503, 1398,
1272, 1232, 1153, 1124, 1099, 1027, 992, 956, 916, 843, 799, 755, 630,
502; MS (ESI) m/z = 299 (M+H)+; (ESI-HRMS) calculated for C13H16O6P
(M+H)+: 299.06790, found: 299.06702.
815, 751, 699, 500; MS (ESI) m/z
=
581 (M+Na)+; (ESI-HRMS)
calculated for C28H32O8NaP2 (M+Na)+: 581.14646, found: 581.14537.
R-Diethyl (2'-hydroxy-[1,1'-binaphthalen]-2-yl) phosphate (5g):
White solid; M.p. 165-167 °C, 51 mg (12%); 1H NMR δ (500 MHz, CDCl3):
8.05 (d, J = 9.0 Hz, 1H), 7.96 (d, J = 8.2 Hz, 1H ), 7.92 (d, J = 9.0 Hz, 1H),
7.86 (d, J = 8.0 Hz, 1H), 7.64(d, J = 9.0 Hz, 1H). 7.48(t, J = 7.0 Hz, 1H),
7.41(d, J = 8.8 Hz, 1H), 7.34(q, J = 6.1 Hz, 2H), 7.23-7.27 (m, 2H), 7.05
(d, J = 8.2 Hz, 1H), 3.92-3.97 (m, 2H), 3.53-3.61 (m, 1H), 3.31-3.39 (m,
1H), 1.21 (t, J = 7.1 Hz, 3H), 0.88 (t, J = 7.0 Hz, 3H); 13C NMR δ (125
MHz, CDCl3): 152.1, 147.2(d, J = 7.2 Hz), 133.7, 131.6, 130.8, 130.0,
129.1, 128.1, 127.8, 127.4, 126.6, 125.9, 125.7, 124.6, 123.6, 122.5,
119.8, 119.6, 116.0, 64.7 (d, J = 6.3 Hz), 64.3 (d, J = 6.3 Hz), 15.8 (d, J
= 7.2 Hz), 15.4 (d, J = 6.3 Hz); 31P NMR (202 MHz, CDCl3, ppm): δ -5.0;
IR vmax cm-1: 3051, 2928, 2855, 2346, 1623, 1507, 1434, 1249, 1211,
1060, 1019, 989, 976, 869, 816, 748, 600, 519 MS (ESI) m/z = 445
(M+Na)+; (ESI-HRMS) calculated for C24H23O5NaP (M+Na)+: 445.11753,
found: 445.11410.
Diethyl quinolin-8-yl phosphate (6b):
1
Black oil; 168 mg (59%); H NMR δ (500 MHz, CDCl3): 8.97 (s, 1H), 8.17
(s, 1H), 7.73 (d, J = 7.6 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.48-7.52 (m,
1H), 7.43-7.47 (m, 1H), 4.33-4.42 (m, 4H), 1.37 (t, J = 7.9 Hz, 6H); 13C
NMR δ (75 MHz, CDCl3): 150.2, 146.7 (d, J = 6.3 Hz), 140.9 (d, J = 5.4
Hz), 135.8, 129.6, 126.2, 124.5, 121.7, 119.2 (d, J = 2.7 Hz), 64.7 (d, J =
5.4 Hz), 16.0 (d, J = 6.3 Hz); 31P NMR (202 MHz, CDCl3, ppm): δ -6.0; IR
vmax cm-1:3419, 2982, 2378, 1500, 1472, 1370, 1273, 1164, 1096, 1027,
964, 927, 833, 793, 543; MS (ESI) m/z = 282 (M+H)+; (ESI-HRMS)
calculated for C13H17O4NP (M+H)+: 282.08897, found: 282.08758.
Diethyl 2-methylquinolin-8-yl phosphate (6c):
R-[1,1'-binaphthalene]-2,2'-diyl tetraethyl bis(phosphate) (5ga):
White solid; M.p. 52-55 °C, 129 mg (23%); 1H NMR δ (500 MHz, CDCl3):
7.98 (d, J = 9.0 Hz, 2H), 7.91 (d, J = 8.2 Hz, 2H), 7.79 (d, J = 9.0 Hz, 2H),
7.44 (t, J = 8.0 Hz, 2H), 7.27-7.34 (m, 4H), 3.65-3.77 (m, 4H), 3.46-3.52
(m, 4H), 1.06 (t, J = 7.0 Hz, 6H), 0.84 (t, J= 7.0 Hz, 6H); 13C NMR δ (75
MHz, CDCl3): 146.6 (d, J = 6.6 Hz),133.4, 130.7, 129.9, 127.8, 126.9,
126.1, 125.3, 121.5 (d, J = 8.1 Hz), 119.1, 64.3 (d, J = 6.3 Hz), 64.0 (d, J
= 6.3 Hz), 15.7 (d, J = 6.3 Hz), 15.3 (d, J = 6.3 Hz); 31P NMR (202 MHz,
CDCl3, ppm): δ -7.5; IR vmax cm-1: 2983, 2922, 2377, 1623, 1592, 1507,
1474, 1361, 1277, 1225, 1164, 1100, 1027, 997, 845, 819, 750, 700, 583,
526; MS (ESI) m/z = 559 (M+H)+; (ESI-HRMS) calculated for C28H33O8P2
(M+H)+: 559.16452, found: 559.16348.
Yellow oil; 197 mg (66%); 1H NMR δ (500 MHz, CDCl3): 8.04 (d, J = 8.3
Hz, 1H), 7.60 (d, J = 5.9 Hz, 2H), 7.41 (t, J = 7.7 Hz, 1H), 7.32 (d, J = 8.3
Hz, 1H), 4.38 -4.46 (m, 4H), 2.74 (s, 3H), 1.39 (t, J = 7.0 Hz, 6H); 13C
NMR δ (75 MHz, CDCl3): 159.0, 146.3 (d, J = 7.2 Hz), 140.5 (d, J = 4.5
Hz), 135.8, 127.9, 125.2, 124.4, 122.6, 119.5 (d, J = 2.7 Hz), 64.7 (d, J =
5.4 Hz), 25.4, 16.0 (d, J = 6.3 Hz); 31P NMR (202 MHz, CDCl3, ppm): δ -
6.0; IR vmax cm-1:2982, 2914, 2377, 1603, 1503, 1432, 1251, 1231, 1166,
1095, 1028, 957, 933, 884, 839, 760, 502; MS (ESI) m/z = 318 (M+Na)+;
(ESI-HRMS) calculated for C14H18O4NNaP (M+Na)+: 318.08657, found:
318.08549.
2-(2H-benzo[d][1,2,3]triazol-2-yl)-4-methylphenyl diethyl phosphate
(6d):
S-Diethyl (2'-hydroxy-[1,1'-binaphthalen]-2-yl) phosphate (5h):
White solid; M.p. 142-147 °C, 51 mg (12%); 1H NMR δ (500 MHz, CDCl3):
8.05 (d, J = 9.0 Hz, 1H), 7.96 (d, J = 8.2 Hz, 1H ), 7.92 (d, J = 8.8 Hz, 1H),
7.86 (d, J = 8.0 Hz, 1H), 7.64(d, J = 9.0 Hz, 1H). 7.48(t, J = 7.9 Hz, 1H),
7.41(d, J = 8.8 Hz, 1H), 7.34(q, J = 8.3 Hz, 2H), 7.23-7.28 (m, 3H), 7.05
(d, J = 8.5 Hz, 1H), 3.92-3.98 (m, 2H), 3.53-3.61 (m, 1H), 3.31-3.39 (m,
1H), 1.21 (t, J = 7.0 Hz, 3H), 0.88 (t, J = 7.0 Hz, 3H); 13C NMR δ (125
MHz, CDCl3): 152.1, 147.2(d, J = 7.2 Hz, 133.7, 131.6, 130.8, 130.0,
129.1, 128.1, 127.8, 127.4, 126.6, 125.9, 125.7, 124.6, 123.6, 122.5,
119.8, 119.6, 116.0, 64.7 (d, J = 6.3 Hz), 64.3 (d, J = 6.3 Hz), 15.8 (d, J
= 7.2 Hz), 15.4 (d, J = 6.3 Hz); 31P NMR (202 MHz, CDCl3, ppm): δ –5.0;
IR vmax cm-1: 3051, 2981, 2929, 2350, 1623, 1593, 1507, 1434, 1249,
1220, 1029, 990, 869, 816, 749, 702, 554; MS (ESI) m/z = 423 (M+H)+;
(ESI-HRMS) calculated for C24H24O5P (M+H)+: 423.13559, found:
423.13579.
Yellow oil; 273 mg (75%); 1H NMR δ (500 MHz, CDCl3): 7.94 (q, J = 3.2
Hz, 2H), 7.67 (s, 1H), 7.54 (d, J = 8.4 Hz, 1H), 7.32 (d, J = 6.7 Hz, 2H),
7.32 (d, J = 6.7 Hz, 1H), 4.00-4.11 (m, 4H), 2.43 (s, 3H), 1.18 (t, J = 6.9
Hz, 6H); 13C NMR δ (125 MHz, CDCl3): 144.8, 141.7 (d, J = 6.3 Hz),
135.4, 131.8(d, J = 6.3 Hz), 131.3, 127.3, 127.0, 121.7, 118.2, 64.7(d, J =
6.3 Hz), 20.6, 15.8 (d, J= 6.3 Hz); 31P NMR (202 MHz, CDCl3, ppm): δ -
6.9; IR vmax cm-1:2983, 2925, 2377, 1563, 1511, 1277, 1233, 1164, 1029,
932, 882, 823, 749, 580; MS (ESI) m/z = 362 (M+H)+; (ESI-HRMS)
calculated for C17H21O4N3P (M+H)+: 362.12642, found: 362.12553.
2-(1H-benzo[d]imidazol-2-yl)phenyl diethyl phosphate (6e):
Yellow oil; 214 mg (61%); 1H NMR δ (500 MHz, CDCl3): 8.33 (d, J = 7.4
Hz, 1H), 7.69 (s, 2H), 7.28-7.47 (m, 5H), 4.16-4.33 (m, 4H), 1.33 (t, J =
7.1 Hz, 6H); 13C NMR δ (75 MHz, CDCl3): 148.1, 147.5 (d, J = 7.2 Hz),
131.6, 131.0, 126.0, 122.8, 122.3 (d, J = 6.3 Hz), 121.2, 65.4(d, J = 6.6
Hz), 16.0 (d, J = 7.2 Hz). 31P NMR (202 MHz, CDCl3, ppm): δ -5.2; IR
vmax cm-1:2979, 2377, 1627, 1489, 1454, 1274, 1215, 1163, 1031, 964,
S-[1,1'-binaphthalene]-2,2'-diyl tetraethyl bis(phosphate) (5ha):
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