5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil | 50610-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil
• 英文别名: 5,5-dichloro-6-hydroxy-6-methyldihydrouracil；5,5-dichloro-6-hydroxy-6-methyl-dihydro-pyrimidine-2,4-dione；5,5-Dichlor-6-hydroxy-6-methyl-dihydro-pyrimidin-2,4-dion；5,5-Dichlor-2,4-dioxo-6-hydroxy-6-methyl-hexahydropyrimidin；5,5-dichloro-6-hydroxy-6-methyl-1,3-diazinane-2,4-dione
• CAS: 50610-49-6
• 化学式: C₅H₆Cl₂N₂O₃
• mdl: MFCD24388697
• 分子量: 213.02
• InChiKey: RSAIDGSVPOSEQS-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C (decomp)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil 在 乙酸酐 、 溶剂黄146 、 锌 作用下， 生成 5-氯-6-甲基尿嘧啶
  参考文献：
  名称：

  Cornforth; Huang, Journal of the Chemical Society, 1948, p. 1988

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 双氧水 、 溴 、 氯 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 生成 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil
  参考文献：
  名称：

  Oxidative halogenation of 6-methyluracil

  摘要：

  An efficient method has been developed for the preparation of halo derivatives of 6-methyluracil by employing oxidative halogenation. Elemental halogens and potassium halides were used as the halogenating agents, while NaNO3 and H2O2 were used as the oxidizing agents. Iodination of 6-methyl-uracil leads to 5-iodo-6-methyluracil as the single reaction product, while bromination or chlorination lead to 5-halo-6-methyluracil, 5,5-dihalo-6-hydroxy-6-methyl-5,6-dihydrouracil, or their mixture depending on the acidity of the medium and the ratio of the substrate and reagents. Bromination of 5-chloro-6-methyluracil leads to 5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil, while chlorination of 6-methyl-, 5-bromo-6-methyl-, and 5-chloro-6-methyluracils using gaseous chlorine yields 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil.

  DOI：

  10.1007/s10593-012-1094-z

文献信息

• Electrophilic ipso-substitution in uracil derivatives
  作者：I. B. Chernikova、S. L. Khursan、L. V. Spirikhin、M. S. Yunusov

  DOI：10.1007/s11172-013-0354-0

  日期：2013.11

  Treatment of 5-iodo-1,3,6-trimethyluracil with 50% H2SO4 gives 1,3,6-trimethyluracil; with 5-bromo-1,3,6-trimethyluracil, a mixture of 1,3,6-trimethyluracil and 6-bromomethyl-1,3-dimethyluracil is obtained. 5-Chloro-1,3,6-trimethyluracil remains inert under these conditions. According to the DFT modeling of the reactions of 5-halo-1,3,6-trimethyluracils, a nucleophilic agent can abstract either Hal+ or the methyl proton from the carbocation formed by protonation of the starting halouracil at position 5, which accounts for the formation of two products from the 5-bromo derivative. Under similar conditions, 6-methyluracil dibromohydrin yields N-bromo-5-bromo-6-hydroxymethyluracil. Bromination or chlorination of 5-hydroxymethyl- or 5-formyl-6-methyluracils follows the ipso-substitution scheme leading to 6-methyluracil 5-halo- and 5,5-dihalohydrins.

  5-碘-1,3,6-三甲基尿苷在50%硫酸中处理生成1,3,6-三甲基尿苷；而在5-溴-1,3,6-三甲基尿苷中，则得到1,3,6-三甲基尿苷和6-溴甲基-1,3-二甲基尿苷的混合物。5-氯-1,3,6-三甲基尿苷在这些条件下保持惰性。根据5-卤-1,3,6-三甲基尿苷反应的DFT建模，亲核试剂可以抽象出形成于起始卤代尿苷5位质子化所产生的碳正离子中的Hal+或甲基质子，这解释了为何5-溴衍生化合物会生成两种产物。在相似条件下，6-甲基尿苷二溴醇生成N-溴-5-溴-6-羟甲基尿苷。5-羟甲基或5-醛基-6-甲基尿苷的溴化或氯化遵循邻位取代机制，生成6-甲基尿苷5-卤代物和5,5-二卤醇。
• The Reaction of Hydrochloric Acid with 6-Methyl-5,5-dichloroxyhydrouracil¹
  作者：Treat B. Johnson

  DOI：10.1021/ja01246a055

  日期：1943.6
• Behrend, Justus Liebigs Annalen der Chemie, 1886, vol. 236, p. 58
  作者：Behrend

  DOI：——

  日期：——
• Behrend, Justus Liebigs Annalen der Chemie, 1886, vol. 236, p. 64
  作者：Behrend

  DOI：——

  日期：——
• Behrend, Justus Liebigs Annalen der Chemie, 1886, vol. 236, p. 22
  作者：Behrend

  DOI：——

  日期：——