5-甲氧基-1,3-二甲基嘧啶-2,4-二酮 | 59264-10-7

• 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-甲氧基-1,3-二甲基嘧啶-2,4-二酮
• 英文名称: 5-methoxy-1,3-dimethyluracil
• 英文别名: 5-Methoxy-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione；5-methoxy-1,3-dimethylpyrimidine-2,4-dione
• CAS: 59264-10-7
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: HLNJGHKPYRXTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-甲氧基-1,3-二甲基嘧啶-2,4-二酮 在 三溴化硼 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到5-羟基-1,3-二甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1

  摘要：

  Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 mu M). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced Flavin Fl-(Red) and resembles those catalyzed by dihydropyrimidine clehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-(OOH) for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.11.014
• 作为产物：
  描述：

  重氮甲烷 、 5-羟基尿嘧啶 在 乙醚 作用下， 生成 5-甲氧基-1,3-二甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Biltz; Paetzold, Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 83

  摘要：

  DOI：

文献信息

• Biltz; Paetzold, Justus Liebigs Annalen der Chemie, 1927, vol. 452, p. 79
  作者：Biltz、Paetzold

  DOI：——

  日期：——
• Ohkura, Kazue; Ishihara, Tetsuya; Nakata, Yasunobu, Heterocycles, 2004, vol. 62, p. 213 - 216
  作者：Ohkura, Kazue、Ishihara, Tetsuya、Nakata, Yasunobu、Seki, Koh-Ichi

  DOI：——

  日期：——
• Direct C-C Bond Formation between Thymine Derivatives and Naphthalene through [2+2]-Photocycloaddition
  作者：Kazue Ohkura、Koh-ichi Seki、Tetsuya Ishihara、Hajime Takahashi、Haruko Takechi

  DOI：10.3987/com-05-s(k)55

  日期：——

  In contrast to our previous findings that UV-irradiation of 1,3-dimethylthymine (1a) with naphthalene (2) underwent 1,4-cycloaddition to give an ethenobenzoquinazoline derivative, UV-irradiation of a mixture of 1a and 2 in the presence of piperylene preferentially underwent 1,2-cycloaddition to give cis-tetrahydronaphthocyclobutapyrimidine in high stereoselectivity. Similar irradiation of 1,3-dimethyluracil and its derivatives (1) with substituents at C-5 gave the corresponding cis-1,2-adducts (3) in fair yields.
• Mechanistic aspects of photocycloaddition chemistry. An interesting relationship between substituent effects on 1,4-biradical closure-to-cleavage ratios and photocycloaddition regioselectivity
  作者：Thomas G. Savino、Lois Konicki Chenard、John S. Swenton

  DOI：10.1016/s0040-4039(00)88260-x

  日期：1983.1