1,3-二甲基-5-硝基-巴比妥酸 | 14305-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,3-二甲基-5-硝基-巴比妥酸
• 英文名称: 1,3-dimethyl-5-nitro-pyrimidin-2,4,6(1H,3H,5H)-trione
• 英文别名: 1,3-dimethyl-5-nitro-2,4,6-pyrimidinetrione；1,3-dimethyl-5-nitrobarbituric acid；1,3-dimethyl-5-nitro-pyrimidine-2,4,6-trione；1,3-Dimethyl-5-nitro-barbitursaeure；1,3-Dimethyl-dilitursaeure；1,3-Dimethyl-5-nitropyrimidine-2,4,6(1H,3H,5H)-trione；1,3-dimethyl-5-nitro-1,3-diazinane-2,4,6-trione
• CAS: 14305-99-8
• 化学式: C₆H₇N₃O₅
• 分子量: 201.139
• InChiKey: XMNHVEFLJGTPDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  337.3±45.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)
• 熔点：
  148-149 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933540000

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-5-硝基-巴比妥酸 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以85%的产率得到5-amino-1,3-dimethyl-pyrimidine-2,4,6-(1H,3H,5H)-trione
  参考文献：
  名称：

  一种作用于FGF受体的4,6-二甲基-噁唑并 [5,4-d]嘧啶-5,7（4H,6H）-二酮衍生物

  摘要：

  本发明公开了一种作用于FGF受体的4,6-二甲基-噁唑并[5,4-d]嘧啶-5,7(4H,6H)-二酮衍生物，本发明以1，3-二甲基嘧啶-2，4，6(1H，3H，5H)-三酮为起始原料，用NaNO2进行亚硝化，然后用Na2S2O4还原，再与芳香醛进行Schiff碱反应，最后用SOCl2环合得目标化合物。本发明的4,6-二甲基-噁唑并[5,4-d]嘧啶-5,7(4H,6H)-二酮衍生物对实验用细胞有一定抑制作用，表现出一定的抗肿瘤活性。对于H460细胞，化合物N5a、N5g和N5k的IC50值均小于阳性对照药；对于B16F10细胞，化合物N5f、N5h、N5i和N5k的IC50值小于阳性对照药；对于A549细胞，阳性对照的IC50值偏高，化合物N5f、N5g、N5h和N5l的IC50值均小于该阳性对照药。

  公开号：

  CN103880861B
• 作为产物：
  描述：

  1,3,1',3'-tetramethylhydurilic acid 在 五氯化磷 、 盐酸羟胺 、 水 、 硝酸 、 silver(l) oxide 作用下， 生成 1,3-二甲基-5-硝基-巴比妥酸
  参考文献：
  名称：

  Techow, Chemische Berichte, 1894, vol. 27, p. 3084

  摘要：

  DOI：

文献信息

• Nitration of 2-Substituted Pyrimidine-4,6-diones, Structure and Reactivity of 5,5-<i>gem</i>-Dinitropyrimidine-4,6-diones
  作者：Abraham Langlet、Nikolaj V. Latypov、Ulf Wellmar、Ulf Bemm、Patrick Goede、Jan Bergman、Ivan Romero

  DOI：10.1021/jo025952x

  日期：2002.11.1

  in high yields. The gem-dinitro products were easily attacked by nucleophiles with concomitant formation of gem-dinitroacetyl derivatives, which in turn could be further hydrolyzed to salts of dinitromethane and triureas.

  研究了在硫酸中硝化一些2-取代的嘧啶-4,6-二酮，以高收率获得了以前未知的5,5-gem-dinitropyrimidine-4,6-diones。宝石-二硝基产物很容易受到亲核试剂的攻击，并同时形成了宝石-二硝基乙酰基衍生物，而后者又可以进一步水解为二氯甲烷和三脲的盐。
• 一种作用于FGF受体的4,6-二甲基-噁唑并 [5,4-d]嘧啶-5,7（4H,6H）-二酮衍生物
  申请人：温州医科大学

  公开号：CN103880861B

  公开（公告）日：2016-02-03

  本发明公开了一种作用于FGF受体的4,6-二甲基-噁唑并[5,4-d]嘧啶-5,7(4H,6H)-二酮衍生物，本发明以1，3-二甲基嘧啶-2，4，6(1H，3H，5H)-三酮为起始原料，用NaNO2进行亚硝化，然后用Na2S2O4还原，再与芳香醛进行Schiff碱反应，最后用SOCl2环合得目标化合物。本发明的4,6-二甲基-噁唑并[5,4-d]嘧啶-5,7(4H,6H)-二酮衍生物对实验用细胞有一定抑制作用，表现出一定的抗肿瘤活性。对于H460细胞，化合物N5a、N5g和N5k的IC50值均小于阳性对照药；对于B16F10细胞，化合物N5f、N5h、N5i和N5k的IC50值小于阳性对照药；对于A549细胞，阳性对照的IC50值偏高，化合物N5f、N5g、N5h和N5l的IC50值均小于该阳性对照药。
• Small compound – big colors: synthesis and structural investigation of brightly colored alkaline earth metal 1,3-dimethylviolurates
  作者：Volker Lorenz、Phil Liebing、Matthias Müller、Liane Hilfert、Martin Feneberg、Elias Kluth、Marcel Kühling、Magnus R. Buchner、Rüdiger Goldhahn、Frank T. Edelmann

  DOI：10.1039/d2dt00606e

  日期：——

  diffraction study. An unexpected oxidation reaction of the barium salt Ba(Me2Vio)2 led to formation of the novel mixed-anion salt Ba(Me2Vio)(Me2NO2Barb)·2H2O (8, Me2NO2Barb− = 1,3-dimethyl-5-nitrobarbiturate anion). Compound 8 could also be synthesized deliberately by treatment of Ba(OH)2 with a 1 : 1 mixture of 2 and 1,3-dimethyl-5-nitrobarbituric acid (7, =H(Me2NO2Barb)·H2O). All new compounds were fully characterized

  一系列色彩鲜艳的碱土金属 1,3-二甲基紫酸盐 M(Me 2 Vio) 2已被制备并充分表征。标题化合物 AE(Me 2 Vio) 2 · n H 2 O (AE = Mg, n = 6 ( 3 ); AE = Ca, n = 8 ( 4 ), AE = Sr, n = 6 ( 5 ); AE = Ba，n = 4 ( 6 )) 是通过用 0.5 equiv中和 1,3-二甲基紫尿酸一水合物 (=H(Me 2 Vio)·H 2 O; 2 ) 获得的。相应的金属二氢氧化物 AE(OH)2 . Sr 衍生物5的毛发状外观阻止了单晶的生长。这个问题可以通过结晶冠醚衍生物 Sr(Me 2 Vio) 2 (18-crown-6) ( 5a ) 来解决。分离的盐呈现出从红色到紫色的强烈颜色。制备铍衍生物Be(Me 2 Vio) 2的各种尝试都失败了。相反，如 X 射线衍射研究所示，反应混合物的后处理提
• Klemm,K.; Pruesse,W., Justus Liebigs Annalen der Chemie, 1974, p. 1882 - 1889
  作者：Klemm,K.、Pruesse,W.

  DOI：——

  日期：——
• Gas/Solid Reactions with Nitrogen Dioxide
  作者：Gerd Kaupp、Jens Schmeyers

  DOI：10.1021/jo00122a031

  日期：1995.9

  Numerous gas/solid reactions of nitrogen dioxide with organic substrates are investigated preparatively and mechanistically. Gaseous NO2 reacts with crystalline stable free radicals (nitroxyls 1, verdazyl 6) by electron transfer. The nitrite ions formed are irreversibly oxidized by NO2 via oxygen atom transfer. Solid cation nitrates are formed quantitatively. Thione bonds of thiohydantoins 8 are transformed to carbonyl bonds with formation of sulfur and NO presumably via nitrites as intermediates. Hydantoin 13 oxygenates at its free 5-methylene group via C-H abstraction and nitrite or it undergoes N-1 nitration via N-H abstraction depending on the conditions. Both reactions proceed quantitatively. 1,3-Oxazolidin-2-one (15) gives N-nitration and N-nitrosation with the NO produced. Nonenolized crystalline barbituric acids 17 are quantitatively nitrated (C-N bond formation with radicals) at their methylene groups. 4-Hydroxybenzaldehyde (19) and vanilline (22) give quantitative aromatic nitration (C-N bond formation with arenes) without melting. All possible regioisomers are formed. Solid 9-methylanthracene (26) gives a quantitative yield of its 10-nitro derivative 27. Crystalline anthracene (28) and gaseous NO2 yield 3 primary products 29 (cis; trans) and the new dimeric product 30 as well as the stable secondary products 31 and 32. The gas/solid tetranitration of tetraphenylethylene (33) is severely hindered by the water of reaction. However, a 95% yield of pure tetrakis(p-nitrophenyl)ethylene is obtained if the drying agent MgSO4 . 2H(2)O is admired and the product 34 extracted. The gas/solid procedures avoid solvents and fuming nitric acid. They give pure products without necessity for recrystallization in most cases and they avoid wastes. Atomic force microscopy (AFM) measurements on prominent faces of single crystals of 1a, 11a, 28, and 33 reveal phase rebuildings with well-directed long-range molecular transports. Nanoliquids were only present on (110) of 28. The characteristic AFM features are correlated with known X-ray crystal structure data and compared with previous results. The shape of the features depends on the molecular packing in the crystal bulk and on the molecular shapes. Molecular interpretations of the AFM features are given.