Molecules 2007, 12
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(CH), 145.39 (C=N-NH), 156.09 (C=N-OH); MS (m/z): 277 (M+H+), 299 (M+Na+); Calcd. for
C11H25N4O2P (%): C 47.81, H 9.12, N 20.28; Found (%): C 47.83, H 9.11, N 20.25.
N,N-Dipropylaminoisopropyl-2-(1-methyl-2-oxopropylidene)phosphonohydrazido oxime (4b). 1H-
NMR δ: 0.75 (t , J = 9.70 Hz,6H ,CH3), 1.10 (dd, J = 8.29 Hz, 6H, CH3), 1.25 (dd, J = 8.29 Hz, 6H,
CH3), 1.55 (m, J = 10.35 Hz, 4H, CH2), 1.80 (s, 3H, CH3), 2.05 (s, 3H, CH3), 2.40 (m, JP-H = 27.86 Hz,
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1H, CH), 2.95 (m, J = 11.85 Hz, 4H, CH2), 6.35 (d, JP-H = 25.68, 1H , NH), 7.85 (s, 1H, OH); C-
NMR δ: 9.36 (CH3), 15.30 (CH3), 16.45 (CH3), 19.97 (CH2), 20.86 (CH3), 24.68 (CH3), 31.45 (CH),
42.20 (CH2), 147.87 (C=N-NH), 156.93 (C=N-OH); MS (m/z): 305 (M+H+), 328 (M+Na+); Calcd. for
C13H29N4O2P (%): C 51.30, H 9.60, N 18.41; Found (%): C 51.27, H 9.58, N 18.39.
N,N-Dipropylaminoisopropyl-2-(1-phenyl-2-oxopropylidene)phosphonohydrazido oxime (4c). 1H-
NMR δ: 0.85 (t, J = 10.23 Hz, 6H, CH3), 1.10 (dd, J = 8.56 Hz,6H, CH3), 1.15 (dd, J = 8.56 Hz, 6H,
CH3), 1.45 (m, J = 9.36 Hz, 4H,CH2), 2.10 (s, 3H, CH3), 2.35 (s, 3H, CH3), 2.30 (m, JP-H = 31.52 Hz,
1H, CH), 2.95 (m, J = 10.54 Hz, 4H, CH2), 6.50 (d, JP-H = 27.59 Hz, 1H, NH), 7.1-7.5 (m, J = 7.93
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Hz, 5H, C6H5), 7.85 (s, 1H, OH); C-NMR δ: 9.58 (CH3), 15.45 (CH3), 16.13 (CH3), 21.97 (CH2),
23.72 (CH3), 31.45 (CH), 46.63 (CH2), 128-130 (Ar-C), 147.64 (C=N-NH), 157.14 (C=N-OH); MS
(m/z): 389 (M+H+), 328 (M+ Na+); Calcd. for C18H31N4O2P (%): C 59.00, H 8.53, N 15.29; Found (%)
: C 58.98, H 8.50, N 15.26.
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N,N-Dibutylaminoisopropyl-2-(1-methyl-2-oxopropylidene)phosphonohydrazido oxime (4d). H-NMR
δ: 0.83( t, J = 12.77 Hz, 6H, CH3), 1.05 (dd, J = 8.51 Hz, 6H, CH3), 1.10 (dd, J = 8.51 Hz, 6H, CH3),
1.25 (m, J = 10.32 Hz, 4H, CH2), 1.45 (m, J = 10.32 Hz, 4H,CH2), 1.78 (s, 3H, CH3), 2.10 (s ,3H,
CH3), 2.40 (m, JP-H = 25.59 Hz,1H, CH),3.05 (m, J = 9.56 Hz, 4H ,CH2), 6.42 (d, JP-H = 20.65 Hz, 1H
,NH), 7.50 (s,1H, OH); 13C- NMR δ: 9.58 (CH3), 15.48 (CH3), 16.05 (CH3),20.36 (CH2), 23.32
(CH3), 24.50 (CH3), 31.03 (CH), 44.72 (CH2), 145.36 (C=N-NH), 155.92 (C=N-OH); MS (m/z): 333
(M+H+) , 355 (M+ Na+) ; Calcd. For C15H33N4O2P (%): C 54.20, H 10.01, N 16.85; Found (%): C
54.18, H 9.98, N 16.85.
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N,N-Dibutylaminoisopropyl-2-(1-phenyl-2-oxopropylidene)phosphonohydrazido oxime (4e). H-NMR
δ: 0.75 (t, J = 11.78 Hz, 6H, CH3), 1.05 (dd, J = 9.37 Hz, 6H, CH3), 1.20 (dd, J = 9.37 Hz, 6H, CH3),
1.45 (m, J = 10.52 Hz, 4H, CH2), 2.05 (s, 3H, CH3), 2.35 (m, JP-H = 26.93 Hz, 1H, CH), 3.05 (m, J =
10.85 Hz, 4H, CH2), 6.15 (d, JP-H = 27.38 Hz, 1H, NH), 7.2-7.5 (m, J = 8.75 Hz, 5H, C6H5), 7.86 (s,
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1H, OH); C-NMR δ: 9.58 (CH3), 15.70 (CH3), 16.05 (CH3), 20.36 (CH2), 23.62 (CH3), 31.32 (CH),
44.74 (CH2), 128-130 (Ar-C), 145.36 (C=N-NH), 155.60 (C=N-OH); MS (m/z): 395 (M+H+); Calcd.
for C20H35N4O2P (%): C 60.89, H 8.94, N 14.20; Found (%): C 60.90, H 8.93 N 14.17.
O-propylisopropyl-2-(1-methyl-2-oxopropylidene)phosphonohydrazido oxime (4f). 1H-NMR δ: 0.85
(t, J = 9.33 Hz, 3H, CH3), 0.95 (dd, J = 7.37 Hz, 3H, CH3), 1.20 (dd, J = 7.23 Hz, 3H, CH3), 1.65 (m,
J = 8.95 Hz, 2H, CH2), 2.20 (m, JP-H = 29.56, 1H, CH), 1.95 (s, 3H, CH3), 2.10 (s, 3H, CH3), 3.90 and
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4.05 (m, J = 9.36 Hz, 2H, CH2), 6.55 (d, JP-H = 26.67 Hz ,1H ,NH), 7.58 (s, 1H, OH); C-NMR δ:
9.63 (CH3), 15.87 (CH3), 16.05 (CH3), 19.20 (CH2), 23.74 (CH3), 24.46 (CH3), 26.53 (CH), 65.49