(S)-2-{4-[1-Dimethylamino-eth-(E)-ylideneamino]-2-oxo-2H-pyrimidin-1-ylmethyl}-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester | 135697-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: (S)-2-{4-[1-Dimethylamino-eth-(E)-ylideneamino]-2-oxo-2H-pyrimidin-1-ylmethyl}-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 135697-15-3
• 化学式: C₁₈H₂₇N₅O₄
• 分子量: 377.443
• InChiKey: SBEPBDNTSAIGRB-HCZVKUGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97.1
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{4-[1-Dimethylamino-eth-(E)-ylideneamino]-2-oxo-2H-pyrimidin-1-ylmethyl}-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 对甲苯磺酰肼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以79%的产率得到(S)-1,1-dimethylethyl 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyl>-5-oxo-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Acyclic nucleic acid analogs: synthesis and oligomerization of .gamma.,4-diamino-2-oxo-1(2H)-pyrimidinepentanoic acid and .delta.,4-diamino-2-oxo-1(2H)-pyrimidinehexanoic acid

  摘要：

  Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base exocyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form. Oligomerization was achieved by activation of the carboxyl group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethylformamide or dimethyl sulfoxide. A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers. The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.

  DOI：

  10.1021/jo00021a010
• 作为产物：
  描述：

  (S)-4-amino-1-<(5-oxo-2-pyrrolidinyl)methyl>-2(1H)-pyrimidinone 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (S)-2-{4-[1-Dimethylamino-eth-(E)-ylideneamino]-2-oxo-2H-pyrimidin-1-ylmethyl}-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Acyclic nucleic acid analogs: synthesis and oligomerization of .gamma.,4-diamino-2-oxo-1(2H)-pyrimidinepentanoic acid and .delta.,4-diamino-2-oxo-1(2H)-pyrimidinehexanoic acid

  摘要：

  Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base exocyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form. Oligomerization was achieved by activation of the carboxyl group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethylformamide or dimethyl sulfoxide. A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers. The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.

  DOI：

  10.1021/jo00021a010