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 | 1203454-23-2

• 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-{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
• 英文别名: 5-trifluoroacetyl-amidoallyl-2'-deoxycytidine；5-(E)-(3-trifluoroacetamidoallyl)-2'-deoxycytidine；N-[(E)-3-[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-5-yl]prop-2-enyl]-2,2,2-trifluoroacetamide
• CAS: 1203454-23-2
• 化学式: C₁₄H₁₇F₃N₄O₅
• 分子量: 378.308
• InChiKey: WYMZPLFAGMLVFK-HFVMFMDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-烯丙基-2,2,2-三氟乙酰胺 、 5-碘-2'-脱氧胞苷 在 lithium acetate 、 四丁基氯化铵 、 N,N-二甲基甲酰胺二甲基缩醛 、 lithium chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 3.0h， 以61%的产率得到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
  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

文献信息

• EP0135587A4
  申请人：——

  公开号：EP0135587A4

  公开（公告）日：1986-04-02
• DEFINED SEQUENCE SINGLE STRAND OLIGONUCLEOTIDES INCORPORATING REPORTER GROUPS, PROCESS FOR THE CHEMICAL SYNTHESIS THEREOF, AND NUCLEOSIDES USEFUL IN SUCH SYNTHESIS
  申请人：SYNGENE, INC.

  公开号：EP0135587B1

  公开（公告）日：1990-05-02
• US4948882A
  申请人：——

  公开号：US4948882A

  公开（公告）日：1990-08-14
• US5541313A
  申请人：——

  公开号：US5541313A

  公开（公告）日：1996-07-30
• US5668266A
  申请人：——

  公开号：US5668266A

  公开（公告）日：1997-09-16