(S)-4-amino-1-<(5-oxo-2-pyrrolidinyl)methyl>-2(1H)-pyrimidinone | 109205-50-7

• 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: (S)-4-amino-1-<(5-oxo-2-pyrrolidinyl)methyl>-2(1H)-pyrimidinone
• 英文别名: 2(1H)-Pyrimidinone, 4-amino-1-[(5-oxo-2-pyrrolidinyl)methyl]-, (S)-；4-amino-1-[[(2S)-5-oxopyrrolidin-2-yl]methyl]pyrimidin-2-one
• CAS: 109205-50-7
• 化学式: C₉H₁₂N₄O₂
• 分子量: 208.22
• InChiKey: AYFFZSGBQBHFJY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  87.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-amino-1-<(5-oxo-2-pyrrolidinyl)methyl>-2(1H)-pyrimidinone 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (S)-1,1-dimethylethyl 2-<<4-(benzoylamino)-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：

  L-焦谷氨醇 在 N-甲基咪唑 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 42.0h， 生成 (S)-4-amino-1-<(5-oxo-2-pyrrolidinyl)methyl>-2(1H)-pyrimidinone
  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

文献信息

• Polynucleotide assay reagent and method
  申请人：ANTIVIRALS INC.

  公开号：EP0639582A2

  公开（公告）日：1995-02-22

  The invention provides a use of a morpholino subunit of the formula (I) where P is a purine or pyrimidine base-pairing moiety, and T is H or an N-protective group, for the production of a polymer capable of hydrogen-bonding to complementary bases in a polynucleotide, where in said polymer (i) the subunits are joined predominantly by substantially uncharged, achiral linkages, and (ii) each linkage joins the morpholino nitrogen of one subunit to the 5' exocyclic carbon of an adjacent subunit.

  本发明提供了式 (I) 吗啉亚基的用途 其中 P 是嘌呤或嘧啶碱基配对分子，T 是 H 或 N 保护基团，用于生产能够与多核苷酸中的互补碱基发生氢键连接的聚合物，在所述聚合物中，(i) 亚基主要通过基本上不带电的非手性连接物连接，(ii) 每个连接物将一个亚基的吗啉基氮连接到相邻亚基的 5'外环碳上。
• EP0215942A4
  申请人：——

  公开号：EP0215942A4

  公开（公告）日：1988-08-23
• STEREOREGULAR POLYNUCLEOTIDE-BINDING POLYMERS
  申请人：SUMMERTON, James

  公开号：EP0216860A1

  公开（公告）日：1987-04-08
• EP0216860A4
  申请人：——

  公开号：EP0216860A4

  公开（公告）日：1989-02-22
• POLYNUCLEOTIDE ASSAY REAGENT AND METHOD
  申请人：SUMMERTON, James

  公开号：EP0215942A1

  公开（公告）日：1987-04-01