4-amino-5-(3-amino-propenyl)-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one | 1262527-27-4

• 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: 4-amino-5-(3-amino-propenyl)-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
• 英文别名: (E)-5-aminoallyl-2'-deoxycytidine
• CAS: 1262527-27-4
• 化学式: C₁₂H₁₈N₄O₄
• 分子量: 282.299
• InChiKey: RCAHALIWJMSLLX-HFVMFMDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136.62
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  N-{3-[4-amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-allyl}-2,2,2-trifluoro-acetamide 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以85%的产率得到4-amino-5-(3-amino-propenyl)-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
  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