SU431172A1 - Method of producing 2,2-dialkyl-3-hydroxy-pdan-1-opt-3-dialkyl phosphonates - Google Patents
Method of producing 2,2-dialkyl-3-hydroxy-pdan-1-opt-3-dialkyl phosphonatesInfo
- Publication number
- SU431172A1 SU431172A1 SU1814227A SU1814227A SU431172A1 SU 431172 A1 SU431172 A1 SU 431172A1 SU 1814227 A SU1814227 A SU 1814227A SU 1814227 A SU1814227 A SU 1814227A SU 431172 A1 SU431172 A1 SU 431172A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dialkyl
- pdan
- opt
- hydroxy
- producing
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YATVHPCKCBERKE-UHFFFAOYSA-N 3-hydroxy-2,2-dimethyl-3h-inden-1-one Chemical compound C1=CC=C2C(=O)C(C)(C)C(O)C2=C1 YATVHPCKCBERKE-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- WLUODQDXJNAOEQ-UHFFFAOYSA-N dibutyl(trihydroxy)-$l^{5}-phosphane Chemical compound CCCCP(O)(O)(O)CCCC WLUODQDXJNAOEQ-UHFFFAOYSA-N 0.000 description 1
- CPUDLRLOFJLISR-UHFFFAOYSA-N diethyl(trihydroxy)-$l^{5}-phosphane Chemical compound CCP(O)(O)(O)CC CPUDLRLOFJLISR-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Description
Изобретение относитс к способу получени новых биологически активных соединений общей формулы где R, R и R - алкил, которые могут найти при:менение в качестве лекарственных веществ . Основанный на известной реакции взаимодействи триалкилфосфитов с кетонами и дикетонами предлагаемый способ получени 2,2-диалкил-З - гидроксииндан-1-он-З-диалкилфосфонатов состоит в том, что 2,2-диалкилиндандион-1 ,3 общей формулы где R и R - как указано выше, обрабатывают диалкилфосфитами в присутствии основани , например триэтиламина, с последующим выделением целевого продукта известными приемами. Полученные соединени устойчивы в обычных услови х, мало токсичны и обладают биологической активностью. Пример 1. К 3,45 г (1М) 2,2-диметилиндандиона-1 ,3 приливают смесь 5,46 г (2А1) диэтилфосфористой кислоты и 2 г (1М) триэтиламина , выдерживают в закрытой колбе при комнатной температуре, на следующий день отдел ют кристаллы 2,2-диметил-З-гидроксииндан-1-он-З-диэтилфосфоната и промывают их на фильтре петролейным эфиром. Выход 5,4 г (87,3%); т. пл. 163°С. Найдено, %: С 57,91; 57,41; Н 6,86; 6,87; Р 9,90; 9,84. CisHaiOsP. Вычислено, %: С 57,69; Н 6,73; Р 9,94. Строение продукта подтверждено ИК- и ЯМР (Рз1)-спектрами. Пример 2. К 0,32 г (1М) 2,2-диметилиндандиона-1 ,3 приливают 0,35 (1М) ди-н-бутилфосфористой кислоты и 0,2 г (1М) триэтиламина , выдерживают 3 дн в закрытой колбе при комнатной температуре, отдел ют 3 кристаллы 2,2-диметил-3-гидроксииндан-1-он ТД:5п 9 ° 1по 7 1П.ОГ тл Выход 0,2 г (30%); т. пл. .104°С. Из фильтрата после промывани кристаллов петролеиным эфиро:м выдел ют еще 0,2 г целевого про-5 дукта. Выход основного продукта увеличиваетс при промывании кристаллов охлажденным петролеиным эфиром. 4 Предмет изобретени получени 2,2-диалкил-З-гидроксииндан-Ьон-З-диалкилфосфонатов , отличающийс тем, что диалкилфосфиты подвергают взаимодействию с 2,2 диалкилиндандио„Q . в присутствии основани с последующ м выделением целевого продукта известны ,и приемамиThe invention relates to a process for the preparation of new biologically active compounds of the general formula </ BR> where R, R and R are alkyl, which can be found as: medicinal substances. Based on the known reaction of trialkylphosphites with ketones and diketones, the proposed method for the preparation of 2,2-dialkyl-3-hydroxyindan-1-one-3-dialkylphosphonates consists in the fact that 2,2-dialkylindandion-1, 3 of the general formula </ BR> where R and R - as indicated above, is treated with dialkyl phosphites in the presence of a base, for example triethylamine, followed by isolation of the target product by known methods. The resulting compounds are stable under normal conditions, are slightly toxic and have a biological activity. Example 1. A mixture of 5.46 g of (2A1) diethylphosphorous acid and 2 g (1M) of triethylamine is added to 3.45 g (1M) of 2,2-dimethyl dianedione-1, 3, and kept in a closed flask at room temperature the next day 2,2-dimethyl-3-hydroxyindan-1-one-3-diethylphosphonate crystals are separated and washed on the filter with petroleum ether. Yield 5.4 g (87.3%); m.p. 163 ° C. Found,%: C 57.91; 57.41; H 6.86; 6.87; P 9.90; 9.84. CisHaiOsP. Calculated,%: C 57.69; H 6.73; R 9.94. The structure of the product is confirmed by IR and NMR (Pz1) -spectra. Example 2. 0.35 (1M) di-n-butylphosphorous acid and 0.2 g (1M) triethylamine are poured into 0.32 g (1M) 2,2-dimethyl-dianedione-1, 3 and kept for 3 days in a closed flask at at room temperature, 3 crystals of 2,2-dimethyl-3-hydroxyindan-1-one are separated. TD: 5n 9 ° 1po 7 1P.Og tl Yield 0.2 g (30%); m.p. .104 ° C. After washing the crystals with petroleum ether: m, another 0.2 g of the desired product was isolated from the filtrate. The yield of the main product is increased by washing the crystals with cooled petroleum ether. 4 An object of the invention for the preparation of 2,2-dialkyl-3-hydroxyindan-Bon-3-dialkylphosphonates, characterized in that the dialkylphosphites are reacted with 2.2 dialkylindandio "Q. in the presence of a base, followed by isolation of the desired product, are known, and
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1814227A SU431172A1 (en) | 1972-07-14 | 1972-07-14 | Method of producing 2,2-dialkyl-3-hydroxy-pdan-1-opt-3-dialkyl phosphonates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1814227A SU431172A1 (en) | 1972-07-14 | 1972-07-14 | Method of producing 2,2-dialkyl-3-hydroxy-pdan-1-opt-3-dialkyl phosphonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU431172A1 true SU431172A1 (en) | 1974-06-05 |
Family
ID=20522984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1814227A SU431172A1 (en) | 1972-07-14 | 1972-07-14 | Method of producing 2,2-dialkyl-3-hydroxy-pdan-1-opt-3-dialkyl phosphonates |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU431172A1 (en) |
-
1972
- 1972-07-14 SU SU1814227A patent/SU431172A1/en active
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