5,6-dihydro-5,6-dihydroxy-6-methyluracil

• 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: 5,6-dihydro-5,6-dihydroxy-6-methyluracil
• 英文别名: 5,6-Dihydroxy-6-methyl-1,3-diazinane-2,4-dione；5,6-dihydroxy-6-methyl-1,3-diazinane-2,4-dione
• 化学式: C₅H₈N₂O₄
• 分子量: 160.13
• InChiKey: QPTVPJIQODTDLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 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：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-5,6-dihydroxy-6-methyluracil 在 乙二胺四乙酸 、 硫酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 5-羟基-6-甲基嘧啶-2,4(1H,3H)-二酮
  参考文献：
  名称：

  A new synthesis of 5-hydroxy-6-methyluracil

  摘要：

  Dehydration of 5,6-dihydro-5,6-dihydroxy-6-methyl- and 5,6-dihydro-5,6-dihydroxy-1,3,6-trimethyluracil in 0.4 M aqueous sulfuric acid gives 5-hydroxy-6-methyl- and 5-hydroxy-1,3,6-trimethyluracil in quantitative yields. Two possible mechanisms have been examined using the mPW1k/6-311+G(2df,2pd)//mPW1k/6-31+G(d,p) method for the transformation of methylated and non-methylated 5,6-dihydro-5,6-dihydroxy-6-methyluracils into the corresponding 5-hydroxy-6-methyluracils. The first is a hydride C5-C6 shift occurring in concert with the loss of a water molecule and formation of the corresponding protonated 5,6-dihydro-5-oxo-6-methyluracils. The second is an acid-catalyzed dehydration reaction to yield 5-hydroxy-6-methyluracils. The calculations demonstrated that the second pathway was energetically most favorable. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.133
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 硫酸 作用下， 以 水 为溶剂， 生成 5,6-dihydro-5,6-dihydroxy-6-methyluracil
  参考文献：
  名称：

  Kinetics of oxidation of certain pyrimidines by Ce(IV)

  摘要：

  The kinetics of the oxidation of certain biologically important pyrimidine bases (Uracil, Thymine, and 6-Methyluracil) by Ce(IV) in aqueous H2SO4 has been investigated. A first-order dependence of rate each on /Ce(IV)/. [pyrimidine], and an inverse first-order dependence on /H2SO4/ has been observed. Rate and activation parameters for the oxidation of these pyrimidines have been computed. A suitable rate law and a mechanism consistent with the kinetic observations and product analysis have been proposed. (C) 1996 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1996)28:10<713::aid-kin1>3.0.co;2-q

文献信息

• Kinetics of oxidation of certain pyrimidines by Ce(IV)
  作者：S. Lakshmi、R. Renganathan

  DOI：10.1002/(sici)1097-4601(1996)28:10<713::aid-kin1>3.0.co;2-q

  日期：——

  The kinetics of the oxidation of certain biologically important pyrimidine bases (Uracil, Thymine, and 6-Methyluracil) by Ce(IV) in aqueous H2SO4 has been investigated. A first-order dependence of rate each on /Ce(IV)/. [pyrimidine], and an inverse first-order dependence on /H2SO4/ has been observed. Rate and activation parameters for the oxidation of these pyrimidines have been computed. A suitable rate law and a mechanism consistent with the kinetic observations and product analysis have been proposed. (C) 1996 John Wiley & Sons, Inc.
• Krishna, Kondamudi Venkata; Jaya Prakash Rao, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1998, vol. 37, # 12, p. 1106 - 1110
  作者：Krishna, Kondamudi Venkata、Jaya Prakash Rao

  DOI：——

  日期：——
• Suvarna Latha; Adinarayana; Jayaprakash Rao, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1999, vol. 38, # 11, p. 1184 - 1187
  作者：Suvarna Latha、Adinarayana、Jayaprakash Rao

  DOI：——

  日期：——
• A new synthesis of 5-hydroxy-6-methyluracil
  作者：Stanislav A. Grabovskiy、Yuri I. Murinov、Natalia N. Kabal’nova

  DOI：10.1016/j.tetlet.2012.08.133

  日期：2012.11

  Dehydration of 5,6-dihydro-5,6-dihydroxy-6-methyl- and 5,6-dihydro-5,6-dihydroxy-1,3,6-trimethyluracil in 0.4 M aqueous sulfuric acid gives 5-hydroxy-6-methyl- and 5-hydroxy-1,3,6-trimethyluracil in quantitative yields. Two possible mechanisms have been examined using the mPW1k/6-311+G(2df,2pd)//mPW1k/6-31+G(d,p) method for the transformation of methylated and non-methylated 5,6-dihydro-5,6-dihydroxy-6-methyluracils into the corresponding 5-hydroxy-6-methyluracils. The first is a hydride C5-C6 shift occurring in concert with the loss of a water molecule and formation of the corresponding protonated 5,6-dihydro-5-oxo-6-methyluracils. The second is an acid-catalyzed dehydration reaction to yield 5-hydroxy-6-methyluracils. The calculations demonstrated that the second pathway was energetically most favorable. (C) 2012 Elsevier Ltd. All rights reserved.