2-[(D-gluco-1,2,3,4,5-pentahydroxyl)pentyl]benzothiazole | 28074-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-[(D-gluco-1,2,3,4,5-pentahydroxyl)pentyl]benzothiazole
• 英文别名: 2-(D-Gluco-pentahydroxypentyl)-benzothiazol；(1R)-1-benzothiazol-2-yl-D-arabinitol；(1R,2S,3R,4R)-1-(1,3-benzothiazol-2-yl)pentane-1,2,3,4,5-pentol
• CAS: 28074-73-9
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: SNBWKUSVRMVCKB-CZULRBLNSA-N

物化性质

• 沸点：
  626.9±55.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-葡萄糖 、 2-氨基苯硫醇 在 3,6-二-2-吡啶基-1,2,4,5-四嗪 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以84%的产率得到2-[(D-gluco-1,2,3,4,5-pentahydroxyl)pentyl]benzothiazole
  参考文献：
  名称：

  Photocatalysis by 3,6-Disubstituted-s-Tetrazine: Visible-Light Driven Metal-Free Green Synthesis of 2-Substituted Benzimidazole and Benzothiazole

  摘要：

  s-Tetrazine based molecules were prepared for visible-light-driven organic transformations. The 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) derivative shows visible light absorption and reversible one-electron reduction behavior. In the presence of pytz and aerial oxygen, aldehyde reacts with o-phenylenediamine or o-aminothiophenol under visible light irradiation at ambient temperature to produce corresponding 2-substituted benzimidazoles and benzothiazoles, respectively. Pytz catalyst demonstrates excellent catalytic activity for alkyl, aryl, organo-metallic substituted aldehydes and reducing sugar. The reaction yield is high for both the electron-donating and electron withdrawing substituents in aromatic aldehydes. The use of a metal-free catalyst and visible light energy, along with the mild reaction conditions, makes this reaction an environmentally benign and energy-saving chemical process.

  DOI：

  10.1021/jo401445j

文献信息

• Photocatalysis by 3,6-Disubstituted-<i>s</i>-Tetrazine: Visible-Light Driven Metal-Free Green Synthesis of 2-Substituted Benzimidazole and Benzothiazole
  作者：Suvendu Samanta、Sudipto Das、Papu Biswas

  DOI：10.1021/jo401445j

  日期：2013.11.15

  s-Tetrazine based molecules were prepared for visible-light-driven organic transformations. The 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) derivative shows visible light absorption and reversible one-electron reduction behavior. In the presence of pytz and aerial oxygen, aldehyde reacts with o-phenylenediamine or o-aminothiophenol under visible light irradiation at ambient temperature to produce corresponding 2-substituted benzimidazoles and benzothiazoles, respectively. Pytz catalyst demonstrates excellent catalytic activity for alkyl, aryl, organo-metallic substituted aldehydes and reducing sugar. The reaction yield is high for both the electron-donating and electron withdrawing substituents in aromatic aldehydes. The use of a metal-free catalyst and visible light energy, along with the mild reaction conditions, makes this reaction an environmentally benign and energy-saving chemical process.