(2S,4S)-2-Aminomethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid benzyl ester | 340981-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4S)-2-Aminomethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS: 340981-95-5
• 化学式: C₁₈H₂₂N₄O₄
• 分子量: 358.397
• InChiKey: APICDQNNOBKHQN-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110.42
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-Aminomethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal potassium fluoride 、 sodium hydroxide 、 Celite 、 氢气 、 三乙胺 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 生成 (2S,4S)-2-(N-Boc-aminoethyl)-4-thymin-1-ylpyrrolidine-N-acetic acid
  参考文献：
  名称：

  Pyrrolidine Nucleic Acids:  DNA/PNA Oligomers with 2-Hydroxy/Aminomethyl- 4-(thymin-1-yl)pyrrolidine-N-acetic acid

  摘要：

  [GRAPHICS]Synthesis of pyrrolidine-based chiral positively charged DNA analogues is reported, The synthesis of (2S,4S) and (2R,4R) thymin-1-ylpyrrolidine-N-acetic acid, its site specific incorporation in PNA:DNA chimera and PNA, and the study of their binding properties with complementary DNA/RNA sequences is presented.

  DOI：

  10.1021/ol0069655
• 作为产物：
  描述：

  (2S,4S)-2-Azidomethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid benzyl ester 在 镍 氢气 作用下， 以95%的产率得到(2S,4S)-2-Aminomethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Pyrrolidine Nucleic Acids:  DNA/PNA Oligomers with 2-Hydroxy/Aminomethyl- 4-(thymin-1-yl)pyrrolidine-N-acetic acid

  摘要：

  [GRAPHICS]Synthesis of pyrrolidine-based chiral positively charged DNA analogues is reported, The synthesis of (2S,4S) and (2R,4R) thymin-1-ylpyrrolidine-N-acetic acid, its site specific incorporation in PNA:DNA chimera and PNA, and the study of their binding properties with complementary DNA/RNA sequences is presented.

  DOI：

  10.1021/ol0069655