5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-undec-10-ynylpentanamide | 188584-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-undec-10-ynylpentanamide
• CAS: 188584-23-8
• 化学式: C₂₁H₃₅N₃O₂S
• 分子量: 393.594
• InChiKey: LSRZBXDPFPXICH-BJLQDIEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3',5'-双乙酰基-5-碘-脱氧尿苷 、 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-undec-10-ynylpentanamide 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(2,4-dioxo-5-{11-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-undec-1-ynyl}-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Palladium-catalysed attachment of labels with acetylenic linker arms to biological molecules

  摘要：

  Palladium-catalysed coupling has been used to attach a series of fluorescent (acridonyl, pyrenyl, fluoresceinyl, dansyl and ruthenium phenanthrolinyl) and enzymic (biotinyl) labels containing a terminal alkyne to electophilic biological molecules based on amino acids, nucleosides and steroids. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01085-x
• 作为产物：
  描述：

  10-十一碳炔酸 在 lithium aluminium tetrahydride 、 氯化亚砜 、 氨 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-undec-10-ynylpentanamide
  参考文献：
  名称：

  Preparation of biological labels with acetylenic linker arms

  摘要：

  The preparation of a series of fluorescent labels based on acridone, pyrene, fluorescein, dimedlylaminonaphthalenesulphonamide and tris-l,10-phenanthroline ruthenium and an enzymic label based on biotin with spacers containing a terminal acetylene is described. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01084-8

文献信息

• Preparation of biological labels with acetylenic linker arms
  作者：Geoffrey T. Crisp、Jeffrey Gore

  DOI：10.1016/s0040-4020(96)01084-8

  日期：1997.1

  The preparation of a series of fluorescent labels based on acridone, pyrene, fluorescein, dimedlylaminonaphthalenesulphonamide and tris-l,10-phenanthroline ruthenium and an enzymic label based on biotin with spacers containing a terminal acetylene is described. (C) 1997, Elsevier Science Ltd.
• Palladium-catalysed attachment of labels with acetylenic linker arms to biological molecules
  作者：Geoffrey T. Crisp、Jeffrey Gore

  DOI：10.1016/s0040-4020(96)01085-x

  日期：1997.1

  Palladium-catalysed coupling has been used to attach a series of fluorescent (acridonyl, pyrenyl, fluoresceinyl, dansyl and ruthenium phenanthrolinyl) and enzymic (biotinyl) labels containing a terminal alkyne to electophilic biological molecules based on amino acids, nucleosides and steroids. (C) 1997, Elsevier Science Ltd.