5-甲基嘧啶-2,4,6(1H,3H,5H)-三酮 | 2417-22-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-甲基嘧啶-2,4,6(1H,3H,5H)-三酮
• 英文名称: 5-methylbarbituric acid
• 英文别名: 5-methyl-1,3-diazinane-2,4,6-trione
• CAS: 2417-22-3
• 化学式: C₅H₆N₂O₃
• 分子量: 142.114
• InChiKey: GOMAEJQBTWAPAN-UHFFFAOYSA-N

物化性质

• 熔点：
  320-323 °C
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933540000
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  5-甲基嘧啶-2,4,6(1H,3H,5H)-三酮 生成 5-甲基乙内酰脲
  参考文献：
  名称：

  Fahr, Egon; Fecher, Peter; Roth, Georg, Angewandte Chemie, 1980, vol. 92, # 10, p. 858 - 859

  摘要：

  DOI：
• 作为产物：
  描述：

  6-羟基-5,6-二氢胸腺嘧啶 在 氧气 作用下， 生成 5-甲基嘧啶-2,4,6(1H,3H,5H)-三酮
  参考文献：
  名称：

  Fahr, Egon; Fecher, Peter; Roth, Georg, Angewandte Chemie, 1980, vol. 92, # 10, p. 858 - 859

  摘要：

  DOI：

文献信息

• Barbituric acid derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and/or matrix metalloproteinases
  申请人：——

  公开号：US20030229084A1

  公开（公告）日：2003-12-11

  The present application describes novel barbituric acid derivatives of formula I: 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, L, R 1 , R 2 , R 3 , R 4 , R 5 , n, W, U, X, Y, Z, U a , X a , Y a , and Z a are defined in the present specification, which are useful as TNF-&agr; converting enzyme (TACE) and matrix metalloproteinases (MMP) inhibitors.

  本申请描述了式I的新型巴比妥酸衍生物： 1 或其药用可接受的盐或前药形式，其中A、B、L、R 1 、R 2 、R 3 、R 4 、R 5 、n、W、U、X、Y、Z、U a 、X a 、Y a 和Z a 在本规范中定义，这些衍生物可用作TNF-α转化酶（TACE）和基质金属蛋白酶（MMP）抑制剂。
• Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
  作者：Branko S. Jursic、Edwin D. Stevens

  DOI：10.1016/s0040-4039(03)00111-4

  日期：2003.3

  Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate

  通过系统地研究反应条件，开发了用于获得大量取代的5-烷基和5-苄基巴比妥酸的非常有效的制备方法。该过程包括两步准备，其中第二步是还原锌粉/酸。对于制备5-烷基巴比妥酸酯，第一步是制备5-酰基或5-亚烷基巴比妥酸酯。如果5-苄基巴比妥酸酯是目标产物，则第一步包括制备5-亚苄基。无论第一步的性质如何，所有反应的合成产率均约为90％，而分离和纯化仅涉及结晶。
• RADIATION-INDUCED HYDROXYLATION OF THYMINE SENSITIZED BY NITRO COMPOUNDS IN N₂O-SATURATED AQUEOUS SOLUTION
  作者：Takeshi Wada、Hiroshi Ide、Sei-ichi Nishimoto、Tsutomu Kagiya

  DOI：10.1246/cl.1982.1041

  日期：1982.7.5

  Hydroxylation of thymine (1)to give thymine glycol (3) is remarkably promoted by the addition of nitro compounds (2a–f) in the γ-radiolysis of the N2O-saturated aqueous solution, although overall decomposition of 1 is depressed to some extent. The G-value of 3, increases linearly with increasing the one-electron reduction potential of 2a-f.

  通过在 N2O 饱和水溶液的 γ-辐射分解中添加硝基化合物 (2a-f) 显着促进了胸腺嘧啶 (1) 羟基化生成胸腺嘧啶乙二醇 (3)，尽管在一定程度上抑制了 1 的整体分解. G 值为 3，随着 2a-f 的单电子还原电位的增加而线性增加。
• Pyrimidine derivatives having a herbicidal action and an action
  申请人：Ciba-Geigy Corporation

  公开号：US04741760A1

  公开（公告）日：1988-05-03

  N-Pyrimidin-4-yl-N'-sulfonylureas of the formula I and the basic addition salts thereof have herbicidal properties and properties for regulating, especially inhibiting, plant growth: ##STR1## the symbols in this formula having the following meanings: Q is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, amino, lower alkyl or dialkylamino, lower alkoxycarbonyl, formyl, lower alkoxyalkyl, lower alkoxyalkoxy, lower alkylthio, lower alkylsulfinyl or alkylsulfonyl, C.sub.1 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkynyl, R.sub.1 is hydrogen, halogen, nitro, a ketal radical, a carbonyl radical substituted by allyl, haloalkyl, alkoxy or cycloalkyl, or is an oxime radical, a lower alkoxy, lower alkylthio, lower alkyl, lower alkylsulfinyl or sulfonyl group, R.sub.2 and R.sub.3 independently of one another are each hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower alkoxyalkyl, lower alkoxyalkoxy, amino, lower alkyl- or dialkylamino or cyclopropyl, and R.sub.2 and Q together can also form a 2-4-membered carbon chain, which is optionally interrupted by an oxygen or sulfur atom or by the group --NR.sub.5 --, R.sub.4 is hydrogen, halogen, lower alkyl, methoxy, nitro or trifluoromethyl, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.3 -C.sub.4 -alkenyl, X is oxygen, sulfur, --NR.sub.5 --, ##STR2## --CH.dbd.CH-- or an annularly-linked phenyl ring, and Z is oxygen or sulfur.

  公式I的N-嘧啶-4-基-N'-磺酰脲及其碱性盐具有除草性能和调节性能，特别是抑制植物生长的性能：##STR1## 该公式中的符号具有以下含义：Q为卤素、低烷基、低卤代烷基、低烷氧基、低卤代烷氧基、硝基、氨基、低烷基或二烷基氨基、低烷氧羰基、甲酰基、低烷氧基烷基、低烷氧基烷氧基、低烷硫基、低烷基亚砜基或烷基磺酰基，C.sub.1 -C.sub.4 -烯基或C.sub.1 -C.sub.4 -炔基，R.sub.1为氢、卤素、硝基、酮缩合物基、烯丙基、卤代烷基、烷氧基或环烷基取代的羰基，或者是肟基、低烷氧基、低烷硫基、低烷基、低烷基亚砜基或磺酰基，R.sub.2和R.sub.3彼此独立地分别为氢、卤素、低烷基、低卤代烷基、低烷氧基、低卤代烷氧基、低烷硫基、低烷氧基烷基、低烷氧基烷氧基、氨基、低烷基或二烷基氨基或环丙基，R.sub.2和Q也可以共同形成一个2-4个碳原子的链，该链可以选择性地由氧原子或硫原子或--NR.sub.5 --基中断，R.sub.4为氢、卤素、低烷基、甲氧基、硝基或三氟甲基，R.sub.5为氢、C.sub.1 -C.sub.4 -烷基或C.sub.3 -C.sub.4 -烯基，X为氧、硫、--NR.sub.5 --、##STR2## --CH.dbd.CH--或环联苯环，Z为氧或硫。
• Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts
  作者：Branko S Jursic、Donna M Neumann

  DOI：10.1016/s0040-4039(01)00621-9

  日期：2001.6

  Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).

  有效的单-和二-制备合成程序Ç通过钯和巴比土酸溶液的铂催化氢化烷基化巴比土酸衍生物（未取代的，Ñ -单和Ñ，N'二取代的巴比土酸）和羰基化合物（脂族和芳族醛和酮）。