. 2014.

3. . 61–84.

DOI: 10.14258/jcprm.1403061

547.92+547.245+547.327+547.362+547.574+547.831+547.835
:
–

©

*

.

,

.

,

.

,

, .
, 13,
e-mail: dikusar@ifoch.bas-net.by

.

,

.

, 220072, (

),

.

,
2000–2013

,

.
,

,

,

–
,

,

,

,
,

,
.

.
:

,

,

,
,

,

,

,

,
,

,

,

,

,

.

ROR1 RCOOR1
,
[1, 2].
–
,
e-mail: dikusar@ifoch.bas-net.by
–
,
.
,
,
e-mail: potkin@ifoch.bas-net.by
–

,

–

,

,

.

,

:

,

,
, -mail: loc@ifoch.bas-net.by
–
,
,
-mail: petkevich@ifoch.bas-net.by
–
,
,
e-mail: deach@list.ru
*

.

.

,
,

,
-

[3].
–

–
.
-

.

-

62

.

,

.

,

.

.

,

,

–
.
,

[4].
,
hrysanthemum cinerariaefolium.
,

,

,
–

4,

[5].

[6–9].
,
,

-

,

,

,

,

.
,
,

,

.
,
,

.
,
,

,

.

,

,
-

[10].
,
2000–2013

. [11–30].

,
.
1.
-

[6–9, 31–33].
,
,

,

13

-,

-

-

[34],

,

-

,
,

,

.

10

.
[6, 35]

,

4

.

,

.
,
,

.
,

,

,

,
,

,

[12, 14, 15, 22, 27–30].

,

-

63

…
1.1.

[30].
,

37],

:

,

) [36,

,
(
, 4-

,

[38-47],
(

,
[11-15,

)

,
18, 19, 21-23, 27-30].
[48]

-

(1)

(2)

[49],
,
-

.
(1),

,
10-12 .
66-89%.

96%-

(2)
(R1Br)
,

(R1Cl),
-

-

(2).
-

(2)

,

-

[31–33].

RU.0001.512.312
[48].

«
6.07.2000.

»( .

-

),
12

1.2.
[50]
(R=Et) (1).

(1)

(R=Me)
-

,
.

(3)

(1)

-

.
,

,
.

(3)

70–96%.

(3)

,
[31–33].

-

64

.

,

.

,

.

.

[51–53]
(

,

-,

[11–15, 27, 28, 30].

).

2.
.

-

,
.

-

,

«

»

,

,

.
,

,

,
,
,
.

-

,
.
«

»

,

-

,
,
,

-

,
,
2.1.

[54].
1-

[55–58]

1-

(4),

-

1(

,

) (5)

.

(4)

,

,

-

,
24–36

65–83%.
4,41

2.2.
[58, 59]
(6)

1

4,4

(7),
4,41

,
,

-

65

…
(5)

.

-

77–91%.
Me
Me

Me

Me
Me

Me

Me

COCl

ROH
C5H5N

5

Me

ClOC

6

CO2R

COCl

ROH

CO2R

RO2C

C5H5N

5

7

4,41

,
,

.

-

.

–

4,41

[16, 17, 20, 24–26]
c

79–81% [59].

2.3.
–

-

.

,

, 17

,

[60, 61].
[62]

,

-3-

(8).
(5):

–

;

,

[61] –
,

–

,
,

,

, (–)-1R,2S,5R
,

,

.

.

,

,
.

-3-

,

–

3,4,4,
;
-

[63].

2,3,4,4-

-2-

, 3,4,4-

,
,

[10].

[64]

(2,3,4,4-

,

,
.

-2-

)

,
(8)

-

,
.

66

.

,

.

,

.

.

[65]

-

(

),
(9).

(Z)-3,4,4,4-

-2-

,

,

,
,

,

,

2,2(
)

,

,
(

), 2,2,3-

), 2,3,4,5,5-

-2,4-

.

(

-

(9)

,

3,3,4,4,4-

-

.

3,3,4,4,4(9)

(Z)-3,4,4,4(Z)-

-2-

.

,

,

1 : 1 : 1.
(9)

.
[66]

77-88%.
,

-

.
.
[67]

-

,

2-

, (-)-(1R,2S,5R)
,
,
(-)-(2S,5R)

-3,4,4(5):

-3,

, 10,
D,L

2-

,
,

(10).
(
,

,

,
,

,

),
, -

,
,

.

-3,4,4-

-3-

(10)
2-

-3,4,4-

-

-3-

.
1 : 1 : 1.
.

(10)

84-91%.

3.
–

-

(
) [68];

(

):

(B10, Cd113, Gd157
,

,
.),

,

,
,

[68, 69];

–

,
,

,
.

-

67

…

Locher G.L.

1936
.

10
11

[68, 69].
4

,

,

2+

7

Li3+.

-

,
,

.
,

,

,

-

[70].
,

[71].
3.1.

,
[72]

,
,

,

,

,

,

(11)

,

[73].
(5):
10-

,
,

,

,
.

D,L

,

,

,

,
,

,
,

,

, (-)-(1R,2S,5R),

,

, 1,2-

3.2.

,
[74]

,

,

,

,
, 3-

,

,

, (-)-(1R,2S,5R),
,
,

,
,

,

,

,
(12)

,
-

,

,
, 10,

,
,

,
,

, ( )-

,

,
D,L
3-

.
(5):
,
,
, -4-

.

-

(12)
(5)

-

-

68

.

,

.

,

.

.

(

1 : 1 : 1).

-, -

(12)

-

83-93%.

[75-77].

3.3.

(7)-

(1)-

[78]

-

,

- (7),

102,3,3:

:

,
,
[2.2.1]
,

,

- (1)-

,

,

,
,

,

,
-4-

-2,2-

,

,
,

:

(13).
(5) –
,
-(2-

, (-)-(1R,2S,5R), 2-2,2;
.

,
)-

[78]

,
,

-

,

.

- (7)-

- (1)-

(13)

,

(5),
- (7)-

- (1)1 : 1 : 1).

(13)

-

89–94%.
3.4.

-1,7[79]

-1,7(14)

(14).
,
,

,
(5).

-1,7(5)

.

71–90%.

4.
,
,

,

,

-

69

…
,
4-

,

,

,

[80-82].
,

.

[83]

(16) –

2-

(15). 2-

-

,
[6].

2-

(16)

2-

(15)
-,

-

.

(16)

-

2-

86-92%.

.

[84, 85]
,

(17) (
2-(E-

Z)-

,

,

,

7 : 3,

-

[6]),
(18)

-

24-36

.

20–23

.
88%,

74-

(18)

.

[86]

L
(19). L
Mentha arvensis
.
L
(20)

(
L

[6]. L
[6].

L

L

(19)

(20)
-,
L

.
76-90%,

-

(19)

-

.

[87, 88]
-2-

(2,6,6-

(21) (
-1-

)-3-

-2-

-4,

[6]).
(21)

(22) c

-

70

.

,

.

,

.

.
-

.

(21)

87–92%,

.

[6–9].
L-(-)-

[89]
(23)

D,L-, D-(+)(23)

.
D,L-, D-(+)-

L-(-)-

(24) c

-

.
(24)

.
1:1

1 : 1 : 1.
(23)

88–92%.

(4-

)
,

,

,

,
[6].
(25)
(25)

,
[90]
(26).

-

(26)
-,

-

.
(25)

80-90%,

.
HC=NOH

HC=NOC(O)R
(RCO)2O / RCOCl

OMe
26

OMe
25

[91]

(28),
(27)

( -

1:2:2)

.
(18–20

)

24–36 .

71

…
(28)

80–96%.

(27)

,

,
.
88–92%.

(29)

(3,4Cymbopogon javanesis,
[6].
[85, 92]

1:1:1

)
(
(30)

.

)
-

82–92%,
4-3-

[93, 94]

(31).
[2-

-3-(4-

]

,

[6].

[95]

(32),

(
[6].

-

-3,

-2-

.

)

,

,

,

,

[96]

(33),

.

(

,

,

)

,

,

,

.
[6].

-

[97]

(34).
NOH

Me

NOC(O)R
(RCO)2O / RCOCl
Me

34

( -

)

,
,

,

[6].

,
,

-

72

.

,

.

,

.

.

(

) [5].

(35),

7-

-2

[b][1,4]

[98]
.

-3(4 )-

(36)

-

[6].
[99, 100]

(37),
(36)
.
O

O
R1COCl

NOH
Me

NOH
C5H5N

O

Me

O

36

37

5.
,
,

,

.
[2, 6].
,

,
-

–

.
,

,

,

,
,

,

,

-

.
.
,

[54].
5.1.

1,3[101]

(38),

1,34,5-

,
(1–3)

-

1,3-

-1
.

16–18

80–88%

(38).

1,31,3-

.

(38)

73

…

R = R = H; R = H, R = 4-MeO; R + R = 3,4-(OCH2O); R = 2-HO, R = 3-MeO; R = 3-HO, R = 4-MeO;
R = 3-MeO, R = 4-HO, 4-MeCO2, 4-EtCO2, 4-PrCO2, 4-(i-PrCO2), 4-BuCO2, 4-(i-BuCO2), 4-(t-BuCO2),
4-Me(CH2)8CO2, 4-Me(CH2)11CO2, 4-Me(CH2)16CO2, 4-C6H5CO2, 4-[2,5-(C6H3Cl2)CO2], 4-[3-(C6H4NO2)CO2],
4-[4-(C6H4NO2)CO2], 4-MeOCO2, 4-EtOCO2; R = 3-EtO, R = 4-HO, 4-MeO, 4-(MeCO2), 4-(EtCO2), 4-(PrCO2),
4-(i-PrCO2), 4-BuCO2, 4-(i-BuCO2), 4-(t-BuCO2), 4-C6H5CO2, 4-[4-(C6H4Me)CO2], 4-[2,5-(C6H3Cl2)CO2],
4-[3-(C6H4NO2)CO2], 4-[4-(C6H4NO2)CO2], 4-(1-AdCO2), 4-MeOCO2, 4-EtOCO2.
2,21
-3,4,5,6,7,9-

5.2
9-

-(3-1

-5,5-1,8(2 )-

-2-

)

3,3,6,6-

,

.
2,21

-

-(3-

[102, 103]
-5,5-

-2-

) (39),
(1-3)
70-80%.
«

[49]
(39)
,
3,4,5,6,7,9-

3,3,6,6-1

-1,8(2 )(40),

(40)

-

-1»

-

-9-

80–90%.
-

,

.

R = H, R1 = 2-BuO, 4-PhCH2O; R = 2-EtO, R1 = 4-EtO, R = 2-BuO, R1 = 4-BuO, R = 2-PhCH2O,
R = 4-PhCH2O; R = 3-MeO, R1 = 4-MeO, 4-EtO, 4-Me2 HO, 4-BuO, 4-Me2 HCH2O, 4-Me2 H(CH2)2O,
4-Me(CH2)5O, 4-Me(CH2)7O, 4-Me(CH2)14O, 42O, 47 13O, 4-Ph
2O; R = 3-EtO,
1
R = 4-MeO, 4-EtO, 4-Me2 HO, 4-BuO, 4-Me2 HCH2O, 4-Me2 H(CH2)2O, 4-Me(CH2)5O, 4-Me(CH2)7O,
1
1
4-Me(CH2)14O, 47 13O, 4-Ph
2O; R = 3-BuO, R = 4-BuO; R = 3-MeO, R = 4-Ph
2O;
1
1
R = 3-Ph 2O, R = 4-Ph 2O; R = 3-MeO, R = 4-MeOC(O)O, 4-EtOC(O)O, 4-[2-ClC6H4C(O)O],
4-[3-(NO2)C6H4C(O)O]; R = 3-EtO, R1 = 4-MeOC(O)O, 4-EtOC(O)O, 4-[3-(NO2)C6H4C(O)O]
1

5.3.
[104]

3(1)
[49],

-5K2CO3

[105]
96%-

EtOH

(41)

74

.

,

80–96%.

.

,

.

.

(41),

-

,
(42, 43)

75–89%.
,

–

,

-

.

5.4.

,
[106]

,
.
,

(1).

,

,

(44)
5-

(

-3-

-

.

(44)

,

(45).

-

,
(46)
.

[106]

,
(45, 46).
5.5.

4,5-

-3-

[107, 108]

,
4,5-

,

-3(47).

-

75

…
,
,
,

,

-

,

.
,

,

,

.
(5):
,
(

(
,

,

,

, (-)-(1R,2S,5R),

,

,

),

)

(

),

.

,
,
,

,

,

-

.
.

,
2000–2013

.,

[1, 2]

-

,

.
(
(

).

,

,

–
)

-

.
.
[50],
.
,

-

[49]
,

[50].
,c
,

-

[75-77, 109-116].

1.
2.

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.
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.
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.,
.,
.,
.,
.,
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66.
.,
.,
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Dikusar E.A.*, Potkin V.I., Petevich C.K., Kozlov N.G., Rudakov D.A. APPLICATION ETHERS AND ESTERS:
MODERN ASPECTS OF MOLECULAR DESIGN - FROM ODORIFEROUS SUBSTANCES AND BIOLOGICALLY ACTIVE COMPOUNDS TO THE MEDICAL APPLICATIONS OF NANOTECHNOLOGY
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova st., 13, Minsk, 220072,
(Republic of Belarus), e-mail: dikusar@ifoch.bas-net.by
The review article is devoted to technology and the application of essential ester chemical bonds for semi-tion of odoriferous substances and biologically active compounds. In a review of a systematic experimental data obtained in the Institute of
Physical and Organic Chemistry, National Academy of Sciences and published for the period 2000-2013 gg. Esterifying anhydrides and acid chlorides of carboxylic acids containing in its composition carborane, heterocyclic, halide, peroxide group, and
fragments of natural compounds of plant origin - alcohols, phenols, oximes or carbonyl compounds also containing acetylene,
carborane, isoxazole, isothiazole and other pharmacophore moieties or substituents, were obtained corresponding ethers and
esters. Examples of their practical application.
Keywords: ethers, esters, derivatives of vanillin vanilalya, oximes, oxime esters, acetals, azomethines, xanthenes,
carboranes, isoxazoles, isothiazoles, odor analysis, biological activity, nanotechnology, nanomaterials.
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*

Corresponding author.

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Received September 4, 2013
Revised October 30, 2013