RU2690011C1 - 2-(2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoacetic acids, which exhibit fluorescent properties, and a method for production thereof - Google Patents
2-(2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoacetic acids, which exhibit fluorescent properties, and a method for production thereof Download PDFInfo
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- RU2690011C1 RU2690011C1 RU2018128770A RU2018128770A RU2690011C1 RU 2690011 C1 RU2690011 C1 RU 2690011C1 RU 2018128770 A RU2018128770 A RU 2018128770A RU 2018128770 A RU2018128770 A RU 2018128770A RU 2690011 C1 RU2690011 C1 RU 2690011C1
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- ITPGLSYRWYLGMS-UHFFFAOYSA-N NC1=C(C(CC(C1)(C)C)=O)C(C(=O)O)=O Chemical class NC1=C(C(CC(C1)(C)C)=O)C(C(=O)O)=O ITPGLSYRWYLGMS-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 4
- RPUUHJNMJWXIBO-UHFFFAOYSA-N 5-phenyl-4-(3-phenylquinoxalin-2-yl)furan-2,3-dione Chemical class O=C1C(=O)OC(C=2C=CC=CC=2)=C1C1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 RPUUHJNMJWXIBO-UHFFFAOYSA-N 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- AUTYGHSAKXEUSV-UHFFFAOYSA-N 5,5-dimethyl-3-(4-methylanilino)cyclohex-2-en-1-one Chemical class C1=CC(C)=CC=C1NC1=CC(=O)CC(C)(C)C1 AUTYGHSAKXEUSV-UHFFFAOYSA-N 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- 101150065749 Churc1 gene Proteins 0.000 abstract 1
- 102100038239 Protein Churchill Human genes 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- -1 2- (2,6-dioxo-cyclohex-1-yl) -2-oxo-acetic acids Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CBTLTHNUFAXDBE-UHFFFAOYSA-N C12=CC=3OCOC=3C=C2C23CCN(C)C3CCC3C2OC1O3 Chemical compound C12=CC=3OCOC=3C=C2C23CCN(C)C3CCC3C2OC1O3 CBTLTHNUFAXDBE-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- MBPQVWGCNCNOQG-UHFFFAOYSA-N 2-aminocyclohex-2-en-1-one Chemical class NC1=CCCCC1=O MBPQVWGCNCNOQG-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- IAODRFIZLKITMK-UHFFFAOYSA-N furan-2,3-dione Chemical class O=C1OC=CC1=O IAODRFIZLKITMK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
2-(2-Амино-4,4-диметил-6-оксоциклогекс-1-ен-1-ил)-2-оксоуксусные кислоты, проявляющие флуоресцентные свойства и способ их получения2- (2-Amino-4,4-dimethyl-6-oxocyclohex-1-ene-1-yl) -2-oxo-acetic acids, exhibiting fluorescent properties and method for their preparation
Группа изобретений относится к области органической химии, а именно к новым индивидуальным соединениям класса аминоциклогексенонов, которые проявляют флуоресцентные свойства и могут быть использованы в качестве исходных продуктов для синтеза новых гетероциклических систем, а также в качестве веществ для маркировки образцов и добавок для светоотражающих красок.The group of inventions relates to the field of organic chemistry, namely to new individual compounds of the class of aminocyclohexenones, which exhibit fluorescent properties and can be used as starting materials for the synthesis of new heterocyclic systems, as well as substances for labeling samples and additives for light-reflecting paints.
Известны различные решения защиты денежных документов, акций, чеков, кредитных карточек, удостоверений личности, паспортов с использованием специальных красок, в частности красок с изменяющимся эффектом, позволяющих, например, переходить от голубого к зеленому цвету в зависимости от наклона документа, или же красок, которые начинают светиться только при определенном облучении, например, под действием ультрафиолетового излучения (патент США №4175776, МПК В42D15/00, приоритет 27.11.78 г.). Однако ассортимент этих красок в настоящее время невелик.There are various solutions for protecting money documents, stocks, checks, credit cards, identity cards, passports using special colors, in particular colors with varying effects, which allow, for example, to change from blue to green depending on the inclination of the document, or colors, which begin to glow only when a certain irradiation, for example, under the action of ultraviolet radiation (US patent No. 4175776, IPC В42D15 / 00, priority 11.11.78). However, the range of these paints is currently small.
Известно использование специальной краски, содержащей отражающую субстанцию и в случае необходимости алюминиевый порошок (патент США №4066280, МПК В42D 15/00, приоритет 03.01.78 г.). Недостатком применения этой краски является трудоемкость нанесения на документ, что приводит к ограничению зон ее использования относительно общей площади документа.It is known to use a special paint containing a reflective substance and, if necessary, aluminum powder (US Patent No. 4066280, IPC B42D 15/00, priority 01/03/78). The disadvantage of this paint is the complexity of the application on the document, which leads to the limitation of its use areas relative to the total area of the document.
Из открытых источников известен способ синтеза близких по структуре к заявляемым соединениям алкиловых эфиров 2-(2,6-диоксоциклогекс-1-ил)-2-оксоуксусных кислот взаимодействием циклогексан-1,3-дионов с диалкилоксалатами (Ghelani, Satish M. et al. Design, synthesis, characterization, and antimicrobial screening of novel indazole bearing oxadiazole derivatives. Journal of Heterocyclic Chemistry, 54(1), 65-70; 2017) по следующей схеме: From open sources, there is a method of synthesis of alkyl compounds of 2- (2,6-dioxo-cyclohex-1-yl) -2-oxo-acetic acids, which are similar in structure to the claimed compounds, by reacting cyclohexane-1,3-dione with dialkyloxalates (Ghelani, Satish M. et al Design, synthesis, characterization, and antimicrobial screening of novel indazole bearing oxadiazole derivatives. Journal of Heterocyclic Chemistry, 54 (1), 65-70; 2017) according to the following scheme:
Однако данный способ, принятый за прототип, не позволяет получать заявляемые соединения, содержащие замещённую аминогруппу, обладающие флуоресцентными свойствами. However, this method adopted for the prototype, does not allow to obtain the claimed compounds containing substituted amino group, with fluorescent properties.
Задачей изобретения является разработка простого, одностадийного способа получения не описанных в литературе 2-(2-амино-4,4-диметил-6-оксоциклогекс-1-ен-1-ил)-2-оксоуксусных кислот, проявляющих флуоресцентные свойства, а также расширение арсенала средств, используемых в качестве меток для защиты документов от копирования и добавок в светоотражающие краски.The objective of the invention is to develop a simple, one-step method of obtaining not described in the literature 2- (2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl) -2-oxoacetic acids exhibiting fluorescent properties, as well as expansion of the arsenal of tools used as labels to protect documents from being copied and added to reflective paints.
Поставленная задача осуществляется путем кипячения (60-62 град) 3-(алкиламино)- или 3-(ариламино)-5,5-диметилциклогекс-2-ен-1-онов с 5-фенил-4-(3-фенилхиноксалин-2-ил)фуран-2,3-дионами в инертном растворителе по схеме:The task is accomplished by boiling (60-62 degrees) 3- (alkylamino) - or 3- (arylamino) -5,5-dimethylcyclohex-2-en-1-ones with 5-phenyl-4- (3-phenylquinoxalin-2 -il) furan-2,3-diones in an inert solvent according to the scheme:
где (I, II): R=CH2C6H5 (а), R=C6H4CH3-4 (б);where (I, II): R = CH 2 C 6 H 5 (a), R = C 6 H 4 CH 3 -4 (b);
Процесс ведут при кипячении при температуре 60-62°С, в качестве инертного растворителя используют хлороформ.The process is carried out by boiling at a temperature of 60-62 ° C, chloroform is used as an inert solvent.
Проведение реакции при температуре ниже 60°С снижает выход целевых продуктов до нуля вследствие того, что реакция не идет – из реакционной массы выделяются непрореагировавшие исходные вещества; повышение температуры проведения реакции (выше 62°С) вызывает уменьшение выхода целевых продуктов вследствие осмоления.Carrying out the reaction at a temperature below 60 ° C reduces the yield of the target products to zero due to the fact that the reaction does not proceed — unreacted starting materials are released from the reaction mass; an increase in the temperature of the reaction (above 62 ° C) causes a decrease in the yield of the target products due to tarring.
Соединения (IIа,б) в твердом состоянии обладают устойчивой флуоресценцией (излучение в области желтого света при λ=580-595 нм) при облучении УФ-лампой λ=254 нм. Флуоресценция сохраняется при хранении образцов в обычных условиях в течение длительного времени.Compounds (IIa, b) in the solid state have stable fluorescence (radiation in the region of yellow light at λ = 580-595 nm) when irradiated with a UV lamp λ = 254 nm. Fluorescence persists when samples are stored under normal conditions for a long time.
Из патентной и технической литературы не были выявлены способы получения 2-(2-амино-4,4-диметил-6-оксоциклогекс-1-ен-1-ил)-2-оксоуксусных кислот, имеющих сходные признаки с заявляемым способом, а именно, не использовались исходные продукты, растворители, в которых проходит реакция, и интервал температур, на основании чего можно сделать вывод о соответствии заявленного технического решения критерию патентоспособности «новизна» и «изобретательский уровень».From the patent and technical literature were not identified methods for producing 2- (2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl) -2-oxoacetic acids having similar features with the claimed method, namely , the original products, the solvents in which the reaction takes place, and the temperature range were not used, on the basis of which it can be concluded that the claimed technical solution complies with the patentability criteria "novelty" and "inventive step".
Пример 1. Синтез 2-(2-(Бензиламино)-4,4-диметил-6-оксоциклогекс-1-ен-1-ил)-2-оксоуксусной кислоты (IIа). Example 1. Synthesis of 2- (2- (Benzylamino) -4,4-dimethyl-6-oxocyclohex-1-en-1-yl) -2-oxoacetic acid (IIa).
Раствор 0.485 г (0.002 моль) соединения (Iа) и 0.800 г (0.0021 моль) 5-фенил-4-(3-фенилхиноксалин-2-ил)фуран-2,3-диона в 20 мл сухого хлороформа кипятили до обесцвечивания (1-20 минут) при 60-62°С, охлаждали, растворитель упаривали досуха, остаток промывали четыреххлористым углеродом, затирали этанолом. Выход 66%, т.пл. 142-144 °С (из этанола). Найдено, %: С 67.66, Н 6.47, N 4.54, О 21.29. Соединение (IIa) C17H19NO4. Вычислено, %: С 67.76, Н 6.36, N 4.65, О 21.24.A solution of 0.485 g (0.002 mol) of compound (Ia) and 0.800 g (0.0021 mol) of 5-phenyl-4- (3-phenylquinoxalin-2-yl) furan-2,3-dione in 20 ml of dry chloroform was boiled until bleaching (1 -20 minutes) at 60-62 ° C, cooled, the solvent was evaporated to dryness, the residue was washed with carbon tetrachloride, rubbed with ethanol. Yield 66%, mp. 142-144 ° C (from ethanol). Found,%: C 67.66, H 6.47, N 4.54, O 21.29. Compound (IIa) C17H19NO4. Calculated,%: C 67.76, H 6.36, N 4.65, O 21.24.
Пример 2. Синтез 2-(2-(4-Толиламино)-4,4-диметил-6-оксоциклогекс-1-ен-1-ил)-2-оксоуксусной кислоты (IIб). Example 2. Synthesis of 2- (2- (4-Tolylamino) -4,4-dimethyl-6-oxocyclohex-1-ene-1-yl) -2-oxoacetic acid (IIb).
Раствор 0.485 г (0.002 моль) соединения (Iб) и 0.800 г (0.0021 моль) 5-фенил-4-(3-фенилхиноксалин-2-ил)фуран-2,3-диона в 20 мл сухого хлороформа выдерживали 10 минут при 60-62°С, охлаждали, растворитель упаривали досуха, остаток промывали четыреххлористым углеродом, затирали этанолом. Выход 68%, т.пл. 159-161 °С. Найдено, %: С 67.86, Н 6.57, N 4.57, О 21.33. Соединение (IIб) C17H19NO4. Вычислено, %: С 67.76, Н 6.36, N 4.65, О 21.24.A solution of 0.485 g (0.002 mol) of compound (Ib) and 0.800 g (0.0021 mol) of 5-phenyl-4- (3-phenylquinoxalin-2-yl) furan-2,3-dione in 20 ml of dry chloroform was kept for 10 minutes at 60 -62 ° C, cooled, the solvent was evaporated to dryness, the residue was washed with carbon tetrachloride, rubbed with ethanol. Yield 68%, mp. 159-161 ° C. Found,%: C 67.86, H 6.57, N 4.57, O 21.33. Compound (IIb) C17H19NO4. Calculated,%: C 67.76, H 6.36, N 4.65, O 21.24.
Соединения (IIа, б) – бесцветные кристаллические вещества, легкорастворимые в ДМСО, ДМФА, труднорастворимые в воде, нерастворимые в алканах, не дающие положительной пробы на наличие енольного гидроксила со спиртовым раствором хлорида железа (III). Устойчивы при хранении в обычных условиях. Compounds (IIa, b) are colorless crystalline substances, easily soluble in DMSO, DMF, insoluble in water, insoluble in alkanes, and do not give a positive sample for the presence of enolic hydroxyl with an alcoholic solution of ferric chloride (III). Resistant when stored under normal conditions.
В спектре ИК соединения (IIа), снятых в виде пасты в вазелиновом масле, имеются полосы валентных колебаний групп NH и ОН в виде широкой полосы в области 3174 см-1, кетонных и карбоксильной карбонильных групп при 1738, 1732 см-1, 1626 см-1.In the spectrum of IR compounds (IIa), taken as a paste in vaseline oil, there are bands of stretching vibrations of the groups NH and OH in the form of a wide band in the region of 3174 cm -1 , ketone and carboxyl carbonyl groups at 1738, 1732 cm -1 , 1626 cm -1 .
В спектре ИК соединения (IIб), снятых в виде пасты в вазелиновом масле, имеются полосы валентных колебаний групп NH и ОН в виде широкой полосы в области 3142 см-1, кетонных и карбоксильной карбонильных групп при 1734, 1693, 1653 см-1.In the spectrum of IR compounds (IIb), taken as a paste in vaseline oil, there are bands of stretching vibrations of the groups NH and OH in the form of a wide band in the region of 3142 cm -1 , ketone and carboxyl carbonyl groups at 1734, 1693, 1653 cm -1 .
В спектре ПМР соединения (IIа), снятых в растворе в ДМСО-d6, присутствует синглет шести протонов двух метильных групп в положении 4 при 0.97 м.д., синглет двух протонов группы СН2 в положении 3 при 2.18 м.д., синглет двух протонов группы СН2 в положении 5 при 2.70 м.д., дублет двух протонов группы СН2 бензильного радикала при 4.76 м.д., группа сигналов пяти ароматических протонов фенильного радикала в области 7.14-7.43 м.д., триплет протона группы NH при 11.78 м.д. Сигнал протона карбоксильной группы сильно уширен вследствие взаимодействия с водой в растворителе и в спектре ПМР не наблюдается.In the PMR spectrum of compound (IIa) taken in solution in DMSO-d6, there is a singlet of six protons of two methyl groups in position 4 at 0.97 ppm, a singlet of two protons of group CH 2 in position 3 at 2.18 ppm, a singlet two protons of the CH 2 group in position 5 at 2.70 ppm, a doublet of two protons of the CH 2 group of the benzyl radical at 4.76 ppm, a group of signals of five aromatic protons of the phenyl radical in the region of 7.14-7.43 ppm, a triple of the proton of the group NH at 11.78 ppm The proton signal of the carboxyl group is strongly broader due to the interaction with water in the solvent and is not observed in the PMR spectrum.
В спектре ПМР соединения (IIб), снятых в растворе в ДМСО-d6, присутствует синглет шести протонов двух метильных групп в положении 4 при 0.95 м.д., синглет двух протонов группы СН2 в положении 3 при 2.25 м.д., синглет трех протонов метильной группы п-толильной группы, синглет двух протонов группы СН2 в положении 5 при 2.63 м.д., квадруплет четырех ароматических протонов п-толильной группы в области 7.29-7.33 м.д., синглет протона группы NH при 12.90 м.д. Сигнал протона карбоксильной группы сильно уширен вследствие взаимодействия с водой в растворителе и в спектре ПМР не наблюдается.In the PMR spectrum of the compound (IIb) taken in solution in DMSO-d6, there is a singlet of six protons of two methyl groups in position 4 at 0.95 ppm, a singlet of two protons of group CH 2 in position 3 at 2.25 ppm, singlet three protons of the methyl group of the p-tolyl group, a singlet of two protons of the CH 2 group in position 5 at 2.63 ppm, a quadruplet of four aromatic protons of the p-tolyl group in the range of 7.29-7.33 ppm, the singlet of the proton of the NH group at 12.90 m .d The proton signal of the carboxyl group is strongly broader due to the interaction with water in the solvent and is not observed in the PMR spectrum.
Предлагаемый способ прост в осуществлении и позволяет получить неописанные в литературе 2-(2-амино-4,4-диметил-6-оксоциклогекс-1-ен-1-ил)-2-оксоуксусные кислоты с высокими выходами.The proposed method is simple to implement and allows you to get 2- (2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl) -2-oxo acetic acids, which are not described in the literature, with high yields.
Флуоресцентная активность предлагаемых соединений позволяет использовать их в индивидуальном виде и в составах для нанесения флуоресцирующих меток, невидимых при обычном освещении, на денежных купюрах или документах, требующих защиты от кодирования.The fluorescent activity of the proposed compounds allows them to be used individually and in compositions for the application of fluorescent labels that are invisible under normal lighting, on bank notes or documents that require protection from encoding.
Полученные соединения могут использоваться для изготовления флуоресцентных красок, свечение которых вызывается УФ и коротковолновым видимым излучением.The compounds obtained can be used for the manufacture of fluorescent paints, the glow of which is caused by UV and short-wave visible radiation.
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