RU2394831C1 - 2-(n-methylalkoxyphosphonyl)-2-aza-3-thiooxybicyclo[2,2,1]heptene-5 and method of producing said compounds - Google Patents

2-(n-methylalkoxyphosphonyl)-2-aza-3-thiooxybicyclo[2,2,1]heptene-5 and method of producing said compounds Download PDF

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RU2394831C1
RU2394831C1 RU2009106489/04A RU2009106489A RU2394831C1 RU 2394831 C1 RU2394831 C1 RU 2394831C1 RU 2009106489/04 A RU2009106489/04 A RU 2009106489/04A RU 2009106489 A RU2009106489 A RU 2009106489A RU 2394831 C1 RU2394831 C1 RU 2394831C1
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methylalkoxyphosphonyl
compounds
heptene
thiooxybicyclo
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Александр Александрович Кролевец (RU)
Александр Александрович Кролевец
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Государственное образовательное учреждение высшего профессионального образования "Курский государственный технический университет" (КурскГТУ)
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Abstract

FIELD: chemistry. ^ SUBSTANCE: present invention relates to 2-(N-methylalkoxyphosphonyl)-2-aza-3-thiooxybicyclo[2.2.1]heptene-5 of general formula: , where R=i-C3H7, C4H9, i-C4H9, which have zoocide activity, and a method of producing said compounds. The disclosed method lies in treating corresponding methyl-phosphonic acid thionylamide esters with cyclopentadiene in a benzene solution while boiling for 4-5 hours. ^ EFFECT: design of a method of obtaining novel biologically active compounds. ^ 2 cl, 2 ex, 2 tbl

Description

Изобретение относится к области фосфорорганических соединений, в частности к получению 2-(N-метилалкоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]гептенов-5 общей формулы:The invention relates to the field of organophosphorus compounds, in particular the production of 2- (N-methylalkoxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptenes-5 of the general formula:

Figure 00000001
Figure 00000001

где R=i-C3H7, С4Н9, i-C4H9;where R = iC 3 H 7 , C 4 H 9 , iC 4 H 9 ;

которые могут использоваться в качестве зооцидов.which can be used as zoocides.

Задача изобретения - синтез нового класса фосфорорганических соединений, обладающих физиологической активностью.The objective of the invention is the synthesis of a new class of organophosphorus compounds with physiological activity.

Поставленная цель достигается предлагаемым способом получения 2-(N-метилалкоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]гептенов-5, который заключается в обработке эфиров тиониламида метилфосфоновой кислоты циклопентадиеном в растворе бензола в течение 4-5 ч.The goal is achieved by the proposed method for the preparation of 2- (N-methylalkoxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptenes-5, which consists in the treatment of methylphosphonic acid thionylamide esters with cyclopentadiene in a benzene solution for 4-5 hours.

ПРИМЕР 1. 2-(N-метилизопропилоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]-гептен-5EXAMPLE 1. 2- (N-methylisopropyloxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptene-5

К раствору 0,05 моля изопропилового эфира тиониламида метилфосфоновой кислоты в 5 мл абс. бензола при 20°С прибавляли раствор 0,05 моль свежеперегнанного циклопентадиена в 2 мл абс. бензола. Смесь нагревают до кипения и выдерживают 4 ч. Фракционированием получают продукт с выходом 10,1%.To a solution of 0.05 mol of methylphosphonic acid thionylamide isopropyl ether in 5 ml of abs. benzene at 20 ° C was added a solution of 0.05 mol of freshly distilled cyclopentadiene in 2 ml of abs. benzene. The mixture is heated to boiling and incubated for 4 hours. By fractionation, the product is obtained in 10.1% yield.

ПРИМЕР 2. 2-(N-метилизопропилоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]-гептен-5EXAMPLE 2. 2- (N-methylisopropyloxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptene-5

Аналогично вышеприведенному, из 0,05 моль изопропилового эфира тиониламида метилфосфоновой кислоты и 0,05 моль циклопентадиена при кипячении в растворе бензола в течение 5 ч получали продукт с выходом 10,2%.Similarly to the above, from 0.05 mol of methylphosphonic acid thionylamide isopropyl ester and 0.05 mol of cyclopentadiene, while boiling in benzene solution for 5 hours, the product was obtained in 10.2% yield.

Другие 2-(N-метилалкоксифосфонил)-2-аза-3-тиооксобицикло-[2.2.1]гептены-5 получены аналогично. Выход, свойства соединений приведены в таблице 1, а их ИК- и ЯМР 31Р-спектры - в таблице 2.Other 2- (N-methylalkoxyphosphonyl) -2-aza-3-thiooxobicyclo- [2.2.1] heptenes-5 were obtained similarly. The yield, properties of the compounds are shown in table 1, and their IR and NMR 31 P-spectra are shown in table 2.

Физиологическая активность синтезированных соединений определялась на белых мышах весом 20 г при в/м введении. Данные физиологической активности полученных веществ (в мг/кг) представлены в таблице.The physiological activity of the synthesized compounds was determined on white mice weighing 20 g with a / m introduction. Data on the physiological activity of the obtained substances (in mg / kg) are presented in the table.

Соединение (по номеру примера)Connection (by example number) LD50 LD 50 1one 22 22 0,50.5 33 0,180.18

Figure 00000002
Figure 00000002

ТАБЛИЦА 2TABLE 2 Данные ИК- и ЯМР 31Р-спектров N-(метилалкоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]гептенов-5 общей формулы IR and NMR data of 31 P-spectra of N- (methylalkoxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptenes-5 of the general formula

Figure 00000001
Figure 00000001
R=i-C3H7 R = iC 3 H 7 R=С4Н9 R = C 4 H 9 R=i-C4H9 R = iC 4 H 9 ОтнесениеAttribution 30503050 30403040 30443044 ν (CH)ν (CH) 30303030 30293029 30333033 ν (CH)ν (CH) 29802980 29832983 29822982 ν (CH)ν (CH) 29332933 29402940 29202920 ν (CH)ν (CH) 28892889 28702870 28752875 ν (CH)ν (CH) -- 28402840 28502850 ν (CH)ν (CH) 16501650 16491649 16521652 ν (C=C)ν (C = C) 16151615 16201620 16171617 ν (C=C)ν (C = C) 14701470 14751475 14801480 δ (CH3)δ (CH 3 ) 14151415 14141414 14141414 δ (CH=)δ (CH =) 14051405 14081408 14071407 δ (CH=)δ (CH =) 13981398 14001400 13991399 δ (CH=)δ (CH =) 13851385 13801380 13701370 δ (CH3)δ (CH 3 ) 12951295 13011301 13021302 ν (PN)ν (PN) 12781278 12771277 12801280 ν (P=0)ν (P = 0) 12081208 12051205 12031203 ν (C-C)ν (C-C) 11901190 11951195 11801180 ν (CH3) маятн.ν (CH 3 ) 10801080 10751075 10831083 ν (S=O)ν (S = O) 10201020 10221022 10251025 ν (CH3) маятн.ν (CH 3 ) 10151015 10131013 10131013 δ (CH=)δ (CH =) 995995 996996 995995 δ (CH=)δ (CH =) 945945 951951 946946 ν (CH3) маятн.ν (CH 3 ) 887887 890890 880880 ν (CH)ν (CH) 860860 854854 855855 ν (CH)ν (CH) 740740 737737 741741 ν (P-C)ν (P-C) +38,61+38.61 +39,74+39.74 +40,05+40.05 ЯМР 31Р-спектр, δP м.д.NMR 31 P spectrum, δ P ppm

Claims (2)

1. Фосфорорганические соединения 2-(N-метилалкоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]гептены-5 общей формулы:
Figure 00000003

где R - i-C3H7, С4Н9, i-C4H9.1. Organophosphorus compounds 2- (N-methylalkoxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptenes-5 of the general formula:
Figure 00000003

where R is iC 3 H 7 , C 4 H 9 , iC 4 H 9 . 2. Способ получения 2-(N-метилалкоксифосфонил)-2-аза-3-тиооксобицикло[2.2.1]гептенов-5 общей формулы:
Figure 00000003

где R - i-C3H7, С4Н9, i-C4H9;
заключающийся в обработке соответствующих эфиров тиониламида метилфосфоновой кислоты циклопентадиеном в растворе бензола при кипении в течение 4-5 ч. 2. The method of obtaining 2- (N-methylalkoxyphosphonyl) -2-aza-3-thiooxobicyclo [2.2.1] heptenes-5 of the general formula:
Figure 00000003

where R is iC 3 H 7 , C 4 H 9 , iC 4 H 9 ;
consisting in processing the corresponding esters of methylphosphonic acid thionylamide cyclopentadiene in a solution of benzene at boiling for 4-5 hours
RU2009106489/04A 2009-02-24 2009-02-24 2-(n-methylalkoxyphosphonyl)-2-aza-3-thiooxybicyclo[2,2,1]heptene-5 and method of producing said compounds RU2394831C1 (en)

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