4-amino-5-(3-aminoprop-1-en-1-yl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one | 952292-39-6

• 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-aminoprop-1-en-1-yl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
• CAS: 952292-39-6
• 化学式: C₁₂H₁₈N₄O₄
• 分子量: 282.299
• InChiKey: RCAHALIWJMSLLX-IVZWLZJFSA-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

• 作为反应物：
  描述：

  4-amino-5-(3-aminoprop-1-en-1-yl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one 、 3,5-二叔丁基邻苯醌 以 甲醇 为溶剂， 以63%的产率得到5-(E)-[2-(5,7-di-tert-butylbenzoxazol-2-yl)ethenyl]-2'-deoxycytidine
  参考文献：
  名称：

  The “Corey's Reagent,” 3,5-di-tert-butyl-1,2-Benzoquinone, as a Modifying Agent in the Synthesis of Fluorescent and Double-Headed Nucleosides

  摘要：

  A new method for the synthesis of fluorescent nucleosides has been developed. It has been shown that a reaction of benzoquinone with aminopropenyl group at C-5-position of 2'-deoxyuridine or 2'-deoxycytidine and aminopropynyl group at the C-7-position of 8-aza-7-deazaadenosine under extremely mild conditions affords conjugated benzoxazole derivatives of nucleosides, which possess strong fluorescent properties. In a similar reaction 5'-amino-5'-deoxy-nucleosides form double-headed nucleoside derivatives with benzoxazole attached at C-4'-position.

  DOI：

  10.1080/15257770903044598
• 作为产物：
  描述：

  TFA-aa-dC 在 氨 作用下， 以 甲醇 为溶剂， 生成 4-amino-5-(3-aminoprop-1-en-1-yl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  The “Corey's Reagent,” 3,5-di-tert-butyl-1,2-Benzoquinone, as a Modifying Agent in the Synthesis of Fluorescent and Double-Headed Nucleosides

  摘要：

  A new method for the synthesis of fluorescent nucleosides has been developed. It has been shown that a reaction of benzoquinone with aminopropenyl group at C-5-position of 2'-deoxyuridine or 2'-deoxycytidine and aminopropynyl group at the C-7-position of 8-aza-7-deazaadenosine under extremely mild conditions affords conjugated benzoxazole derivatives of nucleosides, which possess strong fluorescent properties. In a similar reaction 5'-amino-5'-deoxy-nucleosides form double-headed nucleoside derivatives with benzoxazole attached at C-4'-position.

  DOI：

  10.1080/15257770903044598

文献信息

• PYRAZOLE-TYPE CYANINE DYE
  申请人：Wako Pure Chemical Industries, Ltd.

  公开号：EP2006289B1

  公开（公告）日：2011-11-30