Chemistry & Biodiversity
10.1002/cbdv.201900111
C h e m . B iod i v e r sit y
2
- (4 - c h l or ob en z yl id en e ) - 3- o xo- u r s- 1 2 -e n - 28- o ic a c i d - (4 -n it roo xy) b u ty l e s te r (4 c) . P ale ye llo w so l id ; y ie ld 4 0 .0 % ; p u r i t y: 9 6 .0 % ; m .p . 1 8 4- 1 8 6 ° C ; I R ( K Br ) c m -1
:
1
2
9 49 (C - H a l ip h ) , 1 7 21 , 1 6 78 (C = O) , 1 6 30 , 1 4 91 , 1 4 56 (C = C) , 1 2 79 , 1 0 1 3 ; H N M R (4 0 0 M H z , C D Cl
ON O ) , 4 . 0 2 - 4 .1 2 (m , 2 H , -OC H
m , 2 H ) , 1 . 9 2 - 1 . 9 6 ( m , 2 H ) , 1 .6 6 - 1 .7 9 (m , 1 0 H ) , 1 .3 9 - 1 .5 2 (m , 6 H ) , 1 .2 5 (t , J = 7 .1 H z , 2 H ) , 1 .1 6 , 1 .1 3 , 0 .9 5 , 0 .9 1 , 0 .8 6 , 0 .7 9 (s , 2 1 H , 7 C H
C D Cl ) δ: 2 0 7. 7 ( C 3 ) , 1 7 7.5 (C 2 8 ) , 1 3 8.6 (C 1 3 ) , 1 3 6.3 (C 1 ‘ ) , 1 3 4. 5 (C 2 ‘ ) , 1 3 4 .5 (C 5 ‘ ) , 1 3 4.4 (C 2 ) , 1 3 1 .6 (C 4 ‘ ) , 1 3 1 .6 (C 6 ‘ ) , 1 2 8.8 (C 3 ‘ ) , 1 2 8.8 (C 7 ‘ ) , 1 2 5. 4 ( C 1 2 ) ,
2 .7 (C H ON O ) , 6 3 . 4 ( C O OC H ) , 5 3 .2 (C 5 ) , 5 3 .2 (C 9 ) , 4 8 .4 (C 4 ) , 4 5 .4 (1 4 ) , 45 .3 (C 1 8 ) , 4 4 .1 (C 1 ) , 4 2 .4 (C 1 7 ) , 3 9 .6 (C 8 ) , 3 9 .3 (C 2 0 ) , 3 9 .0 (C 1 9 ) , 3 6 .9 ( C 1 5 ) , 3 6 . 4
C 1 0 ) , 3 2 . 3 ( C 1 6 ) , 3 0 . 8 ( C 7 ) , 2 9 .8 (C 2 5 ) , 2 8 .1 (C 2 1 ) , 2 5 .1 (C 2 2 ) , 2 4 .8 (C 1 1 ) , 2 3 .9 , 2 3 .9 (O C H C H CH C H O) , 2 3 .5 (C 2 3 ) , 2 2 .9 (C 2 4 ) , 2 1 .3 (C 2 6 ) , 2 0 .4 ( C 6 ) , 1 7 . 2
Cl [M ] 6 9 3.3 7 9 6, Fo u n d 6 9 3 .3 80 0 .
- (4 - b r om o-2 - f lu or o b e n z yl id e n e ) -3 - o xo- u r s- 1 2- e n -28 -o ic a c i d - (2 - n it r oo xy ) e th y l e s te r (4 d ) . P ale ye llo w so l id ; y ie ld 7 2 .5 % ; p u r i t y: 9 4 .2 % ; m .p . 1 5 9- 1 6 0 °C ; IR
3
) δ : 7 .4 8 ( d , J = 1 .6 H z , 1 H , - C H = ) , 7 .3 8 , 7 .3 4 (d d , J = 6 .5 , 2 . 1
H z , 4H , P h -H ) , 5 . 2 8 ( t , J = 7 .0 H z , 1 H , H - 1 2 ) , 4 .4 6 (t , J = 6 . 2 H z, 2 H , - C H
2
2
2
) , 2 .9 6 ( d , J = 1 6 .2 H z , 1 H ) , 2 .2 2 - 2 .2 6 (m , 2 H ) , 2 .0 2 - 2 . 0 4
1
3
(
3
) ; C N M R ( 1 0 0 M H z,
3
7
2
2
2
(
2
2
2
2
+
(C 2 7 ) , 1 7 .0 ( C 3 0 ) , 1 5 . 5 ( C 2 9 ) ; H R - M S (E S I) C al c d f or C4 1 H 5 6 N O
6
2
-
1
1
(
K B r) c m : 2 9 2 0 ( C - H a l ip h ) , 1 7 3 2 , 1 6 8 2 (C = O) , 1 6 3 6 , 1 4 7 9, 1 4 5 6 (C = C ) , 1 2 81 , 1 0 20 ; H N M R (4 0 0 M H z , C D Cl
H ) , 7 .2 9 ( d , J = 9 .4 H z, 1 H , P h -H ) , 7 .2 2 (t , J = 7 .9 H z, 1 H , P h - H ) , 5 .2 7 ( s , 1 H , H - 1 2 ) , 4 .6 2 - 4 .6 6 (m , 2H , - C H ON O
H ) , 2 . 1 7 - 2 . 2 5 ( m , 2 H ) , 1 . 8 9- 2 .0 2 (m , 4 H ) , 1 .6 2 - 1 .7 5 (m , 4 H ) , 1 . 4 2- 1 .5 1 (m , 1 0 H ) , 1 .1 6 , 1 .1 2, 0 .9 6 , 0 .8 7 , 0 .7 8 (s , 2 1 H , 7 C H
C 3 ) , 1 7 7. 4 ( C 2 8 ) , 1 5 9. 4 ( C 3 ‘ ) , 1 3 8.7 (C 1 3 ) , 1 3 6.5 (C 2 ) , 1 3 1 .4 (C 1 ‘ ) , 1 2 9.1 (C 7 ‘ ) , 1 2 7.4 (C 6 ‘ ) , 1 2 5.4 (C 1 2 ) , 1 2 3.1 (C 5 ‘ ) , 1 2 2.8 (C 2 ‘ ) , 1 1 9.6 (C 4 ‘ ) , 7 0 .1 (C H
3
) δ : 7 .5 1 ( s , 1 H , - C H = ) , 7 .3 4 (d , J = 8 .4 H z , 1 H , P h -
) , 4 .2 3 - 4 .3 3 (m , 2 H , - OC H ) , 2 .8 1 (d , J = 1 5 . 9 H z ,
) ; C N M R (1 0 0 M H z , CD Cl ) δ: 2 0 7. 1
ON O ) ,
2
0 .2 (C O OC H ) , 5 3 . 4 (C 5 ) , 5 3 .1 (C 9 ) , 4 8 .4 (C 4 ) , 4 5 .6 (C 1 4 ) , 4 5 .6 (C 1 7 ) , 4 5 .3 (C 1 8 ) , 4 3 .8 (C 1 ) , 3 9 .6 (C 8 ) , 3 9 .5 (C 2 0 ) , 3 9 .0 (C 1 9 ) , 3 6 .8 (C 1 5 ) , 3 6 .6 (C 1 0 ) , 3 2 .3 ( C 1 6 ) ,
2
2
2
1
3
1
3
3
(
2
2
6
3
0 .7 (C 7 ) , 2 8 . 0 ( C 2 1 ) , 2 6 . 4 (C 2 2 ) , 2 4 .3 (C 1 1 ) , 2 3 .6 (C 2 5 ) , 2 3 .0 (C 2 6 ) , 2 1 .3 (C 2 7 ) , 2 0 .3 (C 6 ) , 1 7 .2 (C 2 4 ) , 1 7 .0 (C 2 3 ) , 1 5 .5 (C 3 0 ) , 1 4 .3 (C 2 9 ) ; H R - M S (E S I ) C al c d fo r
+
C
3 9
H
5 1 N O
6
F B r [ M ] 7 2 7. 2 8 8 4, F ou n d 7 2 7.2 8 7 6.
2- (4 - b r om o-2 - f lu or o b e n z yl id e n e ) -3 - o xo- u r s- 1 2- e n -28 -o ic a c id - (3 - n it ro ox y) p rop y l e s te r (4 e ) . P ale ye llo w so l i d ; y ie ld 3 3 .3 % ; p u r it y: 9 6.7 % ; m .p . 1 9 2- 1 95 ° C; IR
- 1
1
(
K B r) c m : 2 9 2 4 ( C - H a l ip h ) , 1 7 2 6 , 1 6 2 8 (C = O) , 1 5 9 5 , 1 4 7 9, 1 4 5 6 (C = C ) , 1 2 79 , 1 2 27 ; H N M R (4 0 0 M H z , C D C l
H ) , 7 .2 9 ( d , J = 9 .4 H z , 1 H , P h - H ) , 7 .2 1 (t , J = 8 .0 H z , 1 H , P h - H ) , 5 .2 5 (s , 1 H , H - 1 2 ) , 4 .4 8 - 4 .5 7 (m , 2 H , - C H ON O
H ) , 2 .1 2 - 2 . 2 5 ( m , 2 H ) , 2 . 0 2- 2 .0 5 (m , 2 H ) , 1 .8 8 - 1 .9 1 (m , 2 H ) , 1 .6 3- 1 .6 5 (m , 4 H ) , 1 .4 6 - 1 .5 1 (m , 8 H ) , 1 .2 4- 1 .2 7 (m , 4 H ) , 1 .1 6 , 1 .1 2 , 0 .9 6 , 0 .8 8 , 0 .8 6 , 0 . 7 7 , ( s , 2 1 H ,
3
) δ : 7 .5 0 ( s , 1 H , - C H = ) , 7 .3 3 (d , J = 8 .6 H z , 1 H , P h -
2
2
) , 4 .0 6 - 4 .1 4 (m , 2 H , - OC H ) , 2 .8 1 ( d , J = 1 6 . 0 H z ,
2
1
1
3
7
C H
3
) ; C N M R ( 1 0 0 M H z, C DC l
3
) δ : 20 7 .1 (C 3 ) , 1 7 7.4 (C 2 8 ) , 1 5 9.4 (C 3 ‘ ) , 1 3 8 .7 (C 1 3 ) , 1 3 6.5 (C 2 ) , 1 3 1 .5 (C 1 ‘ ) , 1 2 9 .2 (C 7 ‘ ) , 1 2 7.4 (C 6 ‘ ) , 1 2 5 .4 (C 1 2 ) , 1 2 3. 1 ( C 5 ‘ ) ,
O N O ) , 6 0 .3 (C OOC H ) , 5 3 .4 (C 5 ) , 4 8 .4 (C 4 ) , 4 5 .6 (C 1 4 ) , 4 5 .3 (C 9 ) , 4 3 .8 (C 1 ) , 4 2 .4 (C 1 7 ) , 3 9 .6 (C 8 ) , 3 9 .3 (C 1 8 ) , 3 9 .0 ( C 2 0 ) , 3 6 . 8
C H C H ON O ) , 2 3 .0 (C 2 3 ) , 2 1 .2 (C 2 4 ) , 2 0 . 3 ( C 6 ) ,
FB r [M ] 7 4 1 .3 0 4 0 , Fo u n d 7 4 1 .3 0 4 5 .
- (4 - b r om o-2 - f lu or o b e n zyl i d e n e ) - 3-o xo- u r s- 1 2- e n -28 -o ic a c i d - (4 - n it r oo xy ) b u ty l e s te r (4 f) . P ale ye ll ow so l i d ; y i e l d 5 4 .1 % ; p u r it y: 9 3 .4 % ; m .p . 2 0 2- 2 0 5 °C ; I R
1
2 2.8 ( C 2 ‘ ) , 1 1 9. 6 ( C 4 ‘ ) , 7 0 .1 (C H
2
2
2
(
C 1 5 ) , 3 6 . 6 ( C 1 0 ) , 3 2 . 3 ( C 1 6 ) , 3 0 .7 (C 7 ) , 2 9 .5 (C 1 9 ) , 2 8 .0 (C 2 1 ) , 2 6 .4 (C 2 2 ) , 2 4 .3 (C 1 1 ) , 2 3 .6 (C 2 5 ) , 2 3 .6 (O C H
2
2
2
2
+
1
7 .2 (C 2 6 ) , 1 7 . 0 ( C 2 7 ) , 1 5 .5 (C 3 0 ) , 1 4 .3 (C 2 9 ) ; H R - M S (E S I) C al cd f or C4 0 H 5 3N O
6
2
-
1
1
(
K B r) c m : 2 9 24 ( C - H a l ip h ) , 1 7 26 , 1 6 7 8 (C = O) , 1 6 28 , 1 5 95 , 1 4 79 (C = C ) , 1 2 7 9 , 1 2 27 ; H N M R (4 0 0 M H z , C D Cl
H , Ph -H ) , 7 .2 8 ( d d , J = 9 .4 , 1 .8 H z , 1 H , P h - H ) , 7.2 1 (t , J = 8 . 0 H z ,1 H , P h - H ) , 5.2 5 (t , J = 6 .6 H z ,1 H , H - 1 2 ) , 4.4 4 - 4 .4 8 (m , 2 H , -C H
.8 1 (d , J = 1 6 . 0 H z , 1 H ) , 2 . 1 2 - 2 .2 4 (m . 2 H ) , 1 .8 6 - 1 .9 1 (m , 2 H ) , 1 . 7 8 - 1 .8 0 (m , 2 H ) , 1 .6 5 - 1 .7 5 (m , 6 H ) , 1 .4 6 - 1 .5 8 (m , 8 H ) , 1 . 3 7 - 1 .4 1 (m , 4 H ) , 1 .1 5 , 1 .1 1 , 1 .0 3 , 0 .9 5 ,
3
) δ: 7 .5 0 (s , 1 H , - C H = ) , 7 .3 3 (d d , J = 8 . 3 , 1 . 6 H z ,
1
2
ON O ) , 3 .9 8- 4 .0 6 (m , 2 H , -OC H ) ,
2
2
2
0
1
3
.8 6 , 0 . 7 8 ( s , 2 1 H , 7 C H
3
) ; C N M R (1 0 0 M H z, CD C l
3
) δ : 2 0 7 .1 (C 3 ) , 1 7 7.5 (C 28 ) , 1 5 9.4 (C 3 ‘ ) , 1 3 8.5 (C 1 3 ) , 1 3 6.6 (C 2) , 1 3 1 .4 (C 1 ‘ ) , 1 2 9.1 (C 7 ‘ ) , 1 2 7 .4 ( C 6 ‘ ) , 1 2 5. 4
O N O ) , 6 3 .4 ( C O OCH ) , 5 3 .4 (C 5 ) , 5 3 .2 (C 9 ) , 4 8 .3 (C 4 ) , 4 5 .6 (C 1 7 ) , 4 5 .3 (C 1 8 ) , 4 3 .8 (C 1 ) , 4 2 .4 (C 1 4 ) , 3 9 . 6
C 8 ) , 3 9 . 3 ( C 2 0 ) , 3 9 . 0 ( C 1 9 ) , 3 6 .9 (C 1 5 ) , 3 6 .6 (C 1 0 ) , 3 2 .4 (C 1 6 ) , 3 0 .8 (C 7 ) , 2 9 .5 (C 2 5 ) , 2 8 .0 (C 2 1 ) , 2 7 .0 (C 2 2 ) , 2 5 .1 (C 1 1 ) , 2 4 .3 , 2 3 .9 (O C H C H CH C H O) , 2 3 . 5
FB r [M ] 7 5 5.3 1 9 7, Fo u n d 7 5 5 .3 20 1 .
(
C
1
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(
C 2 3 ) , 2 3 .0 ( C 2 4 ) , 2 1 . 3 ( C 2 6 ) , 2 0 .3 (C 6 ) , 1 7 .2 (C 2 7 ) , 1 7 .0 (C 3 0 ) , 1 5 .5 (C 2 9 ) ; H R - M S (E S I ) C alc d f or C4 1
H
5 5 N O
6
2- (2 - m e th oxyb e n zyl id e n e ) - 3 -o xo- u r s-1 2 - e n - 28- o ic a c i d - (2 - n it rooxy ) e th y l es te r (4 g ) . P ale ye ll ow so l id ; y i e l d 4 7 .8 % ; p u r it y: 9 8 .0 % ; m .p . 1 7 5- 1 7 7 °C ; I R ( K Br )
c m - 1 : 2 9 4 9 ( C - H a l ip h ) , 1 7 3 2 , 1 6 7 2 (C = O ) , 1 6 3 6 , 1 5 9 7 , 1 4 5 6 (C = C ) , 1 2 81 , 1 1 1 1 ; H N M R (4 0 0 M H z , CD C l
1
) δ: 7 .7 9 ( d , J = 1 .8 H z , 1 H , - C H = ) , 7 .2 8 - 7 .3 3 ( m , 2 H , P h -
ON O ) , 4 .2 2 - 4 .3 1 (m , 2 H , - OCH ) , 3 .8 3 ( s ,
) , 2 . 9 7 ( d , J = 1 5 . 9 H z, 1 H ) , 2 . 1 5 - 2 .2 4 (m , 2 H ) , 1 .9 1 - 2 .0 3 (m , 4 H ) , 1 .6 5 - 1 .7 1 (m , 4 H ) , 1 .4 1 - 1 .5 5 (m , 6 H ) , 1 .2 3 - 1 .3 8 (m , 4 H ) , 0 .9 5 (d , J = 6 .0 H z , 3 H , C H ) ,
) δ: 2 0 7.5 (C 3 ) , 1 7 7.3 (C 2 8 ) , 1 5 8 .5 (C 3 ‘ ) , 1 3 8 . 0 (C 1 3 ) , 1 3 3 .6 (C 1 ‘ ) , 1 3 3.4 (C 2 ) , 1 3 0 . 0 ( C 5 ‘ ) ,
3 0 .0 ( C 7 ‘ ) , 1 2 5. 9 ( C 1 2 ) , 1 2 5.1 (C 2 ‘ ) , 1 2 0 .1 (C 6 ‘ ) , 1 1 0 .8 (C 4 ‘ ) , 7 0 .6 (C H ON O ) , 6 0 .2 (C OOC H ) , 5 5 .6 (O CH ) , 5 3 .4 (C 5 ) , 5 3 .1 (C 9 ) , 4 8 .4 (C 4 ) , 4 5 .4 ( C 1 7) , 4 5 . 3
C 1 8 ) , 4 3 . 7 ( C 1 ) , 4 2 . 3 ( C 1 4 ) , 3 9 .6 (C 8 ) , 3 9 .2 (C 2 0 ) , 3 8 .9 (C 1 9 ) , 3 6 .7 (C 1 5 ) , 3 6 .5 (C 1 0 ) , 3 2 .3 (C 1 6 ) , 3 0 .7 (C 7 ) , 2 9 .6 (C 25 ) , 2 8 .0 (C 2 1 ) , 2 4 .2 (C 1 1 ) , 2 3 .6 ( C 2 2 ) , 2 3 . 5
3
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H , - OCH
3
3
1
3
.1 6 , 1 . 1 2 , 0 . 8 9 , 0 . 8 8 , 0 . 7 7 (s , 1 8 H , 6 CH
3
) ; C N M R (1 0 0 M H z, CD Cl
3
1
2
2
2
3
(
+
(C 2 6 ) , 2 3 .0 ( C 2 7 ) , 2 1 . 2 ( C 2 4 ) , 2 0 .4 (C 6 ) , 1 7 .1 (C 2 3 ) , 1 6 .9 (C 3 0 ) , 1 5 .4 (C 2 9 ) ; H R - M S (E S I ) C alc d f or C4 0
H
5 5 N O
7
[M ] 6 6 1 .3 9 7 9, Fo u n d 6 6 1 .3 98 7 .
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z
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3
) δ: 8 .2 3 (s , 1 H , P h - H ) , 8 . 1 6 ( d , J = 8 .1 H z , 1 H , P h - H ) , 7 .6 9 (d , J
7
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ON O
2
) , 4 .2 3 - 4 .3 2 ( m , 2 H , -
) ,
) δ: 2 0 7.4 (C 3 ) , 1 7 7.2 (C 2 8 ) , 1 4 8.3 (C 1 3) , 1 3 8.2 (C 4 ‘ ) , 1 3 7.6 (C 2 ) , 1 3 6.6 ( C 2 ‘ ) , 1 3 5. 7
C 7 ‘ ) , 1 3 4 .6 ( C 1 ‘ ) , 1 2 9 . 6 ( C 6 ‘ ) , 1 2 5 .5 (C 1 2 ) , 1 2 4 .6 (C 5 ‘ ) , 1 2 3 .0 (C 3 ‘ ) , 7 0 .6 (C H ON O ) , 6 0 .2 (C OOCH ) , 5 3 .2 (C 5 ) , 5 3 .0 (C 9 ) , 4 8 .4 (C 4 ) , 4 5 .5 (C 1 7 ) , 4 5 .3 ( C 1 8 ) , 4 3 . 7
C 1 ) , 4 2 . 3 ( C 1 4 ) , 3 9 . 5 ( C 8 ) , 3 9 .2 (C 2 0 ) , 3 8 .9 (C 1 9 ) , 3 6 .6 (C 1 0 ) , 3 6 .6 (C 1 5 ) , 3 2 .1 (C 1 6 ) , 3 0 .6 (C 7 ) , 2 9 .6 (C 2 5 ) , 2 8 .0 (C 2 1 ) , 2 4 .2 (C 1 1 ) , 2 3 .5 (C 2 2 ) , 2 3 . 5 ( C 2 6 ) ,
OC H
2
) , 2 . 9 6 ( d , J = 1 6 . 2 H z, 1 H ) , 2 .2 1 - 2 .3 0 (m , 2 H ) , 1 .9 8- 2 .0 2 (m , 4 H ) , 1 .6 0 - 1 .7 4 (m , 4 H ) , 1 .4 8 - 1 .5 8 (m , 6 H ) , 1 .2 1 - 1 .3 3 (m , 4 H ) , 0 .9 2 (d , J = 5 .9 H z , 3 H , C H
3
1
3
1
.1 5 , 1 .1 4 , 1 . 1 2 , 0 . 8 8 , 0 . 8 7 , 0 .7 6 (s , 1 8 H , 6 CH ) ; C N M R (1 0 0 M H z, C D Cl
3
3
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2
2
2
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+
2
5 2 2 8
2 .9 (C 2 7 ) , 2 1 . 2 ( C 2 4 ) , 2 0 . 3 (C 6 ) , 1 7 .1 (C 2 3 ) , 1 6 .8 (C 3 0 ) , 1 5 .5 (C 2 9 ) ; H R - M S (E S I) Cal c d f or C3 9 H N O [M + N a] 6 9 9.3 6 1 6, Fo u n d 6 9 9 .3 62 0 .
Ph a rm a col og y
7
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