N-[1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide | 186601-13-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-[1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide
• 英文别名: N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-2-oxopyrimidin-4-yl]acetamide
• CAS: 186601-13-8
• 化学式: C₁₁H₁₄IN₃O₅
• 分子量: 395.154
• InChiKey: XSNBFSICWRWISU-DJLDLDEBSA-N

物化性质

• 密度：
  2.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide 在 二(氰基苯)二氯化钯 吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成
  参考文献：
  名称：

  Nucleosides and nucleotides. 161. Incorporation of 5-(N-aminoalkyl)carbamoyl-2′-deoxycytidines into oligodeoxyribonucleotides by a convenient post-synthetic modification method

  摘要：

  5-Trifluoroethoxycarbonyl-2'-deoxycytidine derivatives were synthesized and incorporated into oligonucleotides. The fully protected oligonucleotides were treated with diaminoethane or 1,6-diaminohexane to give oligonucleotides carrying amino-linkers, which were further derivatized with an intercalator. The properties of these oligonucleotides are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00519-7
• 作为产物：
  描述：

  乙酸酐 、 5-碘-2'-脱氧胞苷 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以96%的产率得到N-[1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide
  参考文献：
  名称：

  Convenient synthesis of (E)-5-aminoallyl-2′-deoxycytidine and some related derivatives

  摘要：

  Preparation via the Heck reaction of 5-(E)-(3-trifluoroacetamidoallyl)-2'-deoxycytidine (3a) and some N4-formamidine protected derivatives is reported. Difficulties with coupling N-allyl-trifluoroacetamide to 5-iodo-2'-deoxycytidine were overcome by using Pd(2)(dba)(3) as catalyst and temporary dimethylformamidine protection of the N4-amine of the nucleoside. Compound 3a was isolated with 60% overall yield by crystallization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.137