SYNTHESIS OF ANALOGS OF JUVENILE HORMONS
249
5.0 Hz), 4.89 m (2H, CH2= ), 5.74 m (1H, HC10),
6.89
(2H, Ha2r,o6m), 7.22 (2H, Ha3r,o4m).
CH2), 1.54 m (2H, H2C3), 2.04 d.t (2H, HC9, J8,9
7.0, J9,10 6.5 Hz), 2.30 t (2H, HC2, J 7.0 Hz), 2.34
s and 2.38 s (6H, CH3arom), 4.18 t (2H, CH2O, J
5.0 Hz), 4.27 t (2H, CH2OAr, J 5.0 Hz), 4.98 m
m
m
13C NMR spectrum( C, ppm): 24.96 t (C3), 28.95 t
(C4), 29.12 t (C8), 29.24 t (C5), 29.33 t (C7), 29.77 t
(C6), 33.83 t (C9), 34.24 t (C2), 62.66 t (CH2OAr),
65. 95 t (CH2O), 114. 21 t (CH2= ), 114.67 d
(Ca2r,o6m), 121.21 d (Ca3r,o5m), 139.23 d (HC10=),
141.95 s (C4arom), 158.56 s (Ca1rom), 173.86 s
(C=O). Found, %: C 65.48; H 7.56; N 4.18.
C19H27NO5. Calculated, %: C 65.31; H 7.79; N 4.01.
(2H, HC11), 5.84 m (1H, HC10), 6.67 d (1H, H6arom
,
J 8.0 Hz), 6.93 d (1H, H4arom, J 8.0 Hz), 7.07 m (1H,
H5arom). 13C NMR spectrum ( C, ppm): 11.59 q
(CH3C2arom), 19.92 q (CH3Ca3rom), 24.74 t (C3), 28.96
t (C4), 29.11 t (C8), 29.33 t (C5), 29.34 t (C7), 29.76
t (C6), 33.84 t (C9), 34.28 t (C2), 61.07 t (CH2OAr),
65.89 t (CH2O), 109.11 d (C6arom), 114.26 t (CH2= ),
2-(3-Phenoxyphenoxy)ethyl 10-undecenoate
1
121.35 s (C2arom), 122.94 d (C4arom), 125.65 d (C5arom),
(XXXII). Yield 0.82 g (69%). IR spectrum (cm ):
780 m, 875 m, 970 s, 1210 s, 1605 m, 1745 s, 3080
137.90 s (Ca3rom), 139.25 d (CH=), 155.88 s (C1arom),
169.21 s (C=O). Found, %: C 75.87; H 9.48.
C21H32O3. Calculated, %: C 75.91; H 9.64.
1
w. H NMR spectrum ( , ppm): 1.25 1.30 m (10H,
CH2), 1.50 m (2H, H2C3), 2.07 d.t (2H, HC9, J8,9
7.0, J9,10 6.5 Hz), 2.33 t (2H, HC2, J 7.0 Hz), 4.12
t (2H, CH2O, J 5.0 Hz), 4.34 t (2H, CH2OAr, J
5.0 Hz), 5.01 m (2H, HC11), 5.80 m (1H, HC10),
2-(2,4-Dichlorophenoxy)ethyl
(XXXV). Yield 0.95 g (85%). IR spectrum (cm ):
10-undecenoate
1
6.48 s (1H, H2arom), 6.53 6.59 m (3H, H4,5,6
arom), 6.93
745 m, 830 m, 890 w, 1060 s, 1110 s, 1125 s, 1225 s,
7.34 m (5Harom). 13C NMR spectrum ( , ppm):
1
1600 m, 1755 s, 3080 w. H NMR spectrum ( , ppm):
C
24.93 t (C3), 28.96 t (C4), 29.12 t (C8), 29.22 t (C5),
29.33 t (C7), 29.71 t (C6), 33.83 t (C9), 34.41 t (C2),
63.41 t (CH2OAr), 66.30 t (CH2O), 101.97 d (C2arom),
1.26 1.30 m (10H, CH2), 1.55 m (2H, H2C3),
2.05 d.t (2H, HC9, J8,9 7.0, J9,10 6.5 Hz), 2.33 t (2H,
HC2, J 7.0 Hz), 4.21 t (2H, CH2O, J 5.0 Hz), 4.67 t
(2H, CH2OAr, J 5.0 Hz), 4.95 m (2H, HC11), 5.84
m (1H, HC10), 6.75 d (4H, Ha6rom, J 8.8 Hz), 7.01
d (1H, H5arom, J 8.8 Hz), 7.36 s (1H, H3arom).
13C NMR spectrum ( C, ppm): 24.74 t (C3), 28.94 t
(C4), 29.15 t (C8), 29.33 t (C2), 29.38 t (C7), 29.72 t
(C6), 33.81 t (C9), 34.18 t (C2), 61.58 t (CH2OAr),
66.32 t (CH2O), 114.28 t (CH2=), 114.65 d (C6arom),
107.38 d (C6arom), 112.08 d (Ca4rom), 114.10 t
(CH2= ), 117.96 d (C ), 120.32 d (C4arom), 129.60 d
2 ,6
arom
3 ,5
and 129.64 d (Ca5rom and C ), 139.29 d (CH=),
arom
156.76 s (C3arom), 158.73 s (C1arom), 159.18 s (C1arom),
178.31 s (C=O). Found, %: C 75.51; H 8.04.
C25H32O4. Calculated, %: C 75.73; H 8.13.
2-(4-Phenoxyphenoxy)ethyl 10-undecenoate
124.10 s (C2arom), 126.92 s (C4arom), 127.53 d (C5arom),
1
(XXXIII). Yield 0.76 g (64%). IR spectrum (cm ):
130.24 d (Ca3rom), 139.27 d (CH=), 152.37 s (C1arom),
169.81 (C=O). Found, %: C 61.46; H 7.18; Cl
19.01. C19H26Cl2O3. Calculated, %: C 61.13; H
7.02; Cl 18.99.
848 m, 854 m, 970 s, 1205 s, 1605 m, 1645 w, 1745
1
s, 3080 w. H NMR spectrum( , ppm): 1.25 1.30 m
(10H, CH2), 1.51 m (2H, H2C3), 2.08 d.t (2H, HC9,
J8,9 7.0, J9,10 6.5 Hz), 2.33 t (2H, HC2, J 7.0 Hz),
4.12 t (2H, CH2O, J 5.0 Hz), 4.32 t (2H, CH2OAr, J
5.0 Hz), 5.05 m (2H, HC11), 5.78 m (1H, HC10),
6.60 7.17 m (9Harom). 13C NMR spectrum ( C, ppm):
2-(Phenoxy)ethyl 3-methyl-2 ,4E-decadienoate
1
(XXXVI). Yield 0.76 g (84%). IR spectrum (cm ):
740 m, 760 w, 1250 s, 1380 s, 1600 m, 1640 m,
24.93
t
(C3), 28.97
t
(C4), 29.14
t
(C8),
1
29.22 t (C5), 29.33 t (C7), 29.77 t (C6), 33.76 t (C9),
34.24 t (C2), 63.44 t (CH2OAr), 66.32 t (CH2O),
114.15 t (CH2= ), 114.29 d (Ca2r,o6m), 118.95 d, 119.05
1720 s, 3080 w. H NMR spectrum ( , ppm): 0.86 t
(3H, CH3, J 6.0 Hz), 1.28 m (6H, CH2), 1.95 d (Z)
and 2.26 d (E) (3H, CH3C=C, J 1.5 Hz), 2.44 t (2H,
H2C6, J 7.5 Hz), 3.97 t (2H, CH2O, J 5.0 Hz), 4.25
t (2H, CH2OAr, J 5.0 Hz), 5.70 br.s (1H, HC2),
6.12 m [HC4 (2E) and HC5], 6.35 m and 7.24 m (5H,
Ar), 7.32 d [HC4 (2Z), J 12.0 Hz]. 13C NMR
spectrum ( C, ppm): 14.16 q and 14.35 q (CH3),
23.94 t (C9), 30.80 t and 30.84 t (C7 and C8), 33.16 t
(C6), 63.56 t (CH2OAr), 66.18 t (CH2O), 114.64 d
(C4arom), 121.18 d (Ca2r,o6m), 124.80 d (C2), 129.54 d
d (Ca3r,o5m and C
, 122.73 d (C
, 129.6 d (C4arom),
2 ,6
3 ,5
arom)
arom)
139.26 (CH=), 150.72 s (C4arom), 154.29 (Ca1rom),
156.87 s (C1arom), 178.38 (C=O). Found, %: C
75.48; H 8.24. C25H32O4. Calculated, %: C 75.73;
H 8.13.
2-(2,3-Dimethylphenoxy)ethyl 10-undecenoate
1
(XXXIV). Yield 0.81 g (81%). IR spectrum (cm ):
(Ca3r,o5m), 131.44 d (C4), 138.96 d (C5), 151.59 s (C3),
705 w, 765 m, 1090 m, 1130 s, 1205 s, 1595 s, 1760
1
158.34 s (C1arom), 166.32 s (C=0). Found, %: C
s. H NMR spectrum ( , ppm): 1.25 1.30 m (10H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 2 2001