2-chloro-1-<3-(1,1-dioxythietanyl)>benzimidazole | 159326-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-chloro-1-<3-(1,1-dioxythietanyl)>benzimidazole
• 英文别名: 2-chloro-1-(1,1-dioxidothietan-3-yl)-1H-benzimidazole；1H-Benzimidazole, 2-chloro-1-(3-thietanyl)-, S,S-dioxide；3-(2-chlorobenzimidazol-1-yl)thietane 1,1-dioxide
• CAS: 159326-43-9
• 化学式: C₁₀H₉ClN₂O₂S
• 分子量: 256.713
• InChiKey: ZYXJYPRAZGLUNP-UHFFFAOYSA-N

物化性质

• 沸点：
  556.5±60.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 2-chloro-1-<3-(1,1-dioxythietanyl)>benzimidazole 在 sodium 作用下， 反应 0.5h， 生成 2-氯苯并咪唑 、 3-ethoxythietane 1,1-dioxide
  参考文献：
  名称：

  Thietane ring as a novel protecting group

  摘要：

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.

  DOI：

  10.1134/s1070428009010187
• 作为产物：
  描述：

  1-(thietan-3-yl)-2-chlorobenzimidazole 在 potassium permanganate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以91%的产率得到2-chloro-1-<3-(1,1-dioxythietanyl)>benzimidazole
  参考文献：
  名称：

  Pharmacological properties of the products of the reaction of epithiochlorhydrin with benzimidazoles

  摘要：

  DOI：

  10.1007/bf00772996

文献信息

• Dioxothietanylation of heterocycles 2*. Imidazoles and benzimidazoles
  作者：Nadezhda N. Makarova、Elena E. Klen、Ferkat А. Khaliullin

  DOI：10.1007/s10593-019-02543-0

  日期：2019.9

  1-Dioxidothietan-3-yl)-1H-imidazoles and 1-(1,1-dioxidothietan-3-yl)-1H-benzimidazoles were synthesized in the reaction of 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole with the sodium salts of imidazoles and benzimidazoles. The reaction involves addition of azoles to thiete 1,1-dioxide formed in situ, which acts as a Michael acceptor. The effect of pKa values of imidazoles and benzimidazoles

  在3,5-dibromo-1反应中合成了1-（1,1-Dioxidothietan-3-yl）-1 H-咪唑和1-（1,1-dioxidothietan-3-yl）-1 H-苯并咪唑-（1,1-二氧噻吩-3-基）-1 H -1,2,4-三唑与咪唑和苯并咪唑的钠盐。该反应涉及将唑类添加到就地形成的1,1-二氧化噻吩中，该噻吩充当迈克尔受体。显示了咪唑和苯并咪唑的p K a值对其反应性的影响。
• Pharmacological properties of the products of the reaction of epithiochlorhydrin with benzimidazoles
  作者：F. A. Khaliullin、V. A. Kataev、A. S. Zaks、N. M. Terekhova、Yu. V. Strokin

  DOI：10.1007/bf00772996

  日期：1993.3
• Thietane ring as a novel protecting group
  作者：F. A. Khaliullin、E. E. Klen

  DOI：10.1134/s1070428009010187

  日期：2009.1

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.