4-((((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methylcarbamoyloxy)methyl)-1-methylpyridinium trifluoromethanesulfonate | 1345959-39-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 4-((((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methylcarbamoyloxy)methyl)-1-methylpyridinium trifluoromethanesulfonate
• 英文别名: (1-methylpyridin-1-ium-4-yl)methyl N-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]carbamate;trifluoromethanesulfonate
• CAS: 1345959-39-8
• 化学式: CF₃O₃S*C₁₈H₂₃N₄O₆
• 分子量: 540.474
• InChiKey: QYWJBDOLPDTTMK-ONAKXNSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-((((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methylcarbamoyloxy)methyl)-1-methylpyridinium trifluoromethanesulfonate 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 维生素 C 作用下， 以 氘代甲醇 为溶剂， 反应 2.0h， 以97%的产率得到amino-5'-deoxythymidine
  参考文献：
  名称：

  Photorelease of Primary Aliphatic and Aromatic Amines by Visible-Light-Induced Electron Transfer

  摘要：

  Visible-light-absorbing tris(bipyridyl)ruthenium(II) has been used to mediate electron transfer to N-methylpicolinium carbamates that undergo C-O bond fragmentation followed by spontaneous carbon dioxide release to give free amines. Release of several aliphatic and aromatic primary amines has been demonstrated under mild conditions using visible light.

  DOI：

  10.1021/ol202456d
• 作为产物：
  描述：

  4-吡啶甲醇 以 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 4-((((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methylcarbamoyloxy)methyl)-1-methylpyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  Photorelease of Primary Aliphatic and Aromatic Amines by Visible-Light-Induced Electron Transfer

  摘要：

  Visible-light-absorbing tris(bipyridyl)ruthenium(II) has been used to mediate electron transfer to N-methylpicolinium carbamates that undergo C-O bond fragmentation followed by spontaneous carbon dioxide release to give free amines. Release of several aliphatic and aromatic primary amines has been demonstrated under mild conditions using visible light.

  DOI：

  10.1021/ol202456d

文献信息

• Photorelease of Primary Aliphatic and Aromatic Amines by Visible-Light-Induced Electron Transfer
  作者：Joseph B. Edson、Liam P. Spencer、James M. Boncella

  DOI：10.1021/ol202456d

  日期：2011.12.2

  Visible-light-absorbing tris(bipyridyl)ruthenium(II) has been used to mediate electron transfer to N-methylpicolinium carbamates that undergo C-O bond fragmentation followed by spontaneous carbon dioxide release to give free amines. Release of several aliphatic and aromatic primary amines has been demonstrated under mild conditions using visible light.