4,5-二氢-5-羟基-5,5'-二甲基-[4,4'-联嘧啶]-2,2',6(1H,3H,3'H)-三酮 | 20545-93-1

• 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: 4,5-二氢-5-羟基-5,5'-二甲基-[4,4'-联嘧啶]-2,2',6(1H,3H,3'H)-三酮
• 英文名称: 5-hydroxy-6-4'-<5'-methylpyrimidin-2'-one>-dihydrothymine
• 英文别名: 5-hydroxy-5,5'-dimethyl-4,5-dihydro-3H,1'(3')H-[4,4']bipyrimidinyl-2,6,2'-trione；5-hydroxy-5-methyl-6-(5-methyl-2-oxo-1H-pyrimidin-6-yl)-1,3-diazinane-2,4-dione
• CAS: 20545-93-1
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: FAIHIWDKQVXTTP-UHFFFAOYSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  beta-胸苷 在 盐酸 作用下， 以 水 为溶剂， 反应 0.33h， 生成 5,5'-二甲基-4,4'-联嘧啶-2,2',6(1H,3H,3'H)-三酮 、 4,5-二氢-5-羟基-5,5'-二甲基-[4,4'-联嘧啶]-2,2',6(1H,3H,3'H)-三酮
  参考文献：
  名称：

  The (5‐4) and (6‐4) Adducts of 1‐Methylthymine and Their Dewar Valence Isomers

  摘要：

  AbstractPrevious studies of the photochemical reaction of 1‐methylthymine (MeT) in frozen aqueous solution have indicated that four cyclobutane type dimers are formed. We have restudied this system and have found that, in addition to cyclobutane dimers, both a (5‐4) adduct and a (6‐4) adduct of MeT are formed in significant amounts. Upon standing in aqueous solution, the (5‐4) adduct is susceptible to reaction to form an isomeric form of the parent adduct, possibly via ring‐opening and closure reactions at C‐6 of the saturated pyrimidine ring component of the adduct. Irradiation of each of these three adducts with UVB light produces a pair of Dewar‐type adducts. The nine products were individually characterized by mass spectrometry, proton NMR spectroscopy and UV spectroscopy. A less comprehensive study showed that irradiation of thymidine in frozen aqueous solution produces a diastereomeric pair of (5‐4) adducts, along with the previously known diastereomeric pair of (6‐4) adducts.

  DOI：

  10.1111/j.1751-1097.2011.00932.x

文献信息

• The (5‐4) and (6‐4) Adducts of 1‐Methylthymine and Their Dewar Valence Isomers
  作者：Martin D. Shetlar、Janet Chung

  DOI：10.1111/j.1751-1097.2011.00932.x

  日期：2011.7

  AbstractPrevious studies of the photochemical reaction of 1‐methylthymine (MeT) in frozen aqueous solution have indicated that four cyclobutane type dimers are formed. We have restudied this system and have found that, in addition to cyclobutane dimers, both a (5‐4) adduct and a (6‐4) adduct of MeT are formed in significant amounts. Upon standing in aqueous solution, the (5‐4) adduct is susceptible to reaction to form an isomeric form of the parent adduct, possibly via ring‐opening and closure reactions at C‐6 of the saturated pyrimidine ring component of the adduct. Irradiation of each of these three adducts with UVB light produces a pair of Dewar‐type adducts. The nine products were individually characterized by mass spectrometry, proton NMR spectroscopy and UV spectroscopy. A less comprehensive study showed that irradiation of thymidine in frozen aqueous solution produces a diastereomeric pair of (5‐4) adducts, along with the previously known diastereomeric pair of (6‐4) adducts.