N-3-(2-hydroxyethyl)thymine | 101852-96-4

• 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: N-3-(2-hydroxyethyl)thymine
• 英文别名: 3-(2-Hydroxyethyl)-5-methylpyrimidine-2,4(1H,3H)-dione；3-(2-hydroxyethyl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 101852-96-4
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: LGUUSMBSCFXTGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-3-(2-hydroxyethyl)thymine 、 Bis-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-phosphinic acid; compound with tert-butyl-methyl-amine 在 吡啶 、 苯甲基-2-磺酰三硝基三氮唑 作用下， 反应 24.0h， 以75%的产率得到Bis-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-phosphinic acid 2-(5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-ethyl ester
  参考文献：
  名称：

  无环核苷的双（羟甲基）次膦酸类似物；合成并掺入短DNA寡聚体

  摘要：

  通过将BHPA的双（4,4'-二甲氧基三苯甲基）衍生物与N -1-或N -3-（2-羟乙基）缩合获得基于双（羟甲基）次膦酸（BHPA）骨架的无环核苷的新类似物。胸腺嘧啶在MSNT的存在下，或与N -1-或N -3-（2-氨基乙基）胸腺嘧啶的Appel反应。选择性脱保护和磷酸化后，它们被用作亚磷酰胺方法自动合成短寡聚物的固体支持物的单体。

  DOI：

  10.1016/s0040-4039(02)01067-5
• 作为产物：
  描述：

  胸腺嘧啶 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 N-3-(2-hydroxyethyl)thymine
  参考文献：
  名称：

  Alkylation of thymine with 1,2-dibromoethane

  摘要：

  Alkylation of thymine with 1,2-dibromoethane depends strongly on the reaction conditions. Various alkyl derivatives may be produced, including N-1- or N-5-monosubstituted alkylthymines and products of their cyclisation, as well higher molecular weight products resulting from intermolecular substitution of N-1- and N-3-mono- and N-1,N-3-dialkylthymines. We have identified two cyclic products 5 and 6 and the dialkylated derivative 7, for which detailed structural analyses have been performed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00277-0

文献信息

• Alkylation of thymine with 1,2-dibromoethane
  作者：B Nawrot、O Michalak、S Olejniczak、M.W Wieczorek、T Lis、W.J Stec

  DOI：10.1016/s0040-4020(01)00277-0

  日期：2001.4

  Alkylation of thymine with 1,2-dibromoethane depends strongly on the reaction conditions. Various alkyl derivatives may be produced, including N-1- or N-5-monosubstituted alkylthymines and products of their cyclisation, as well higher molecular weight products resulting from intermolecular substitution of N-1- and N-3-mono- and N-1,N-3-dialkylthymines. We have identified two cyclic products 5 and 6 and the dialkylated derivative 7, for which detailed structural analyses have been performed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Bis(hydroxymethyl)phosphinic acid analogues of acyclic nucleosides; synthesis and incorporation into short DNA oligomers
  作者：B Nawrot、O Michalak、M Nowak、A Okruszek、M Dera、W.J Stec

  DOI：10.1016/s0040-4039(02)01067-5

  日期：2002.7

  nucleosides based on a bis(hydroxymethyl)phosphinic acid (BHPA) backbone were obtained by condensation of the bis(4,4′-dimethoxytrityl) derivative of BHPA with N-1- or N-3-(2-hydroxyethyl)thymine in the presence of MSNT, or by an Appel reaction with N-1- or N-3-(2-aminoethyl)thymine. After selective deprotection and phosphitylation they were used as monomers for automated solid support synthesis of short oligomers

  通过将BHPA的双（4,4'-二甲氧基三苯甲基）衍生物与N -1-或N -3-（2-羟乙基）缩合获得基于双（羟甲基）次膦酸（BHPA）骨架的无环核苷的新类似物。胸腺嘧啶在MSNT的存在下，或与N -1-或N -3-（2-氨基乙基）胸腺嘧啶的Appel反应。选择性脱保护和磷酸化后，它们被用作亚磷酰胺方法自动合成短寡聚物的固体支持物的单体。