1-(morpholin-4-ylmethyl)-1,3-dihydro-2H-benzimidazole-2-thione | 6268-88-8

• 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: 1-(morpholin-4-ylmethyl)-1,3-dihydro-2H-benzimidazole-2-thione
• 英文别名: 1-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione；1-(morpholin-4-ylmethyl)benzimidazole-2-thione；1-morpholin-4-ylmethyl-1,3-dihydro-benzoimidazole-2-thione；1-Morpholinomethyl-benzimidazolinthion-(2)；1-(Morpholin-4-ylmethyl)-3h-benzo[d]imidazole-2-thione；3-(morpholin-4-ylmethyl)-1H-benzimidazole-2-thione
• CAS: 6268-88-8
• 化学式: C₁₂H₁₅N₃OS
• 分子量: 249.337
• InChiKey: PBKJTNMQGNCQEY-UHFFFAOYSA-N

物化性质

• 沸点：
  387.0±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(morpholin-4-ylmethyl)-1,3-dihydro-2H-benzimidazole-2-thione 在 sodium hydroxide 作用下， 以 氘代二甲亚砜 、 异丙醇 为溶剂， 反应 5.0h， 生成 (1H-苯并咪唑-2-基硫代)乙酸乙酯
  参考文献：
  名称：

  Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione

  摘要：

  Alkylation of 1,3-dihydro-2De-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2De-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.

  DOI：

  10.1007/s10593-014-1623-z
• 作为产物：
  描述：

  聚合甲醛 、 吗啉 、 1H-苯并咪唑-2-硫醇 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以68%的产率得到1-(morpholin-4-ylmethyl)-1,3-dihydro-2H-benzimidazole-2-thione
  参考文献：
  名称：

  Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione

  摘要：

  Alkylation of 1,3-dihydro-2De-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2De-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.

  DOI：

  10.1007/s10593-014-1623-z

文献信息

• Hamama, Journal of Chemical Research - Part S, 2000, # 6, p. 269 - 271
  作者：Hamama

  DOI：——

  日期：——
• Synthesis and spatial structure of 1-(cytisin-1-ylmethyl)benzimidazole-2-thione
  作者：A. M. Gazaliev、M. K. Ibraev、M. B. Isabaeva、Zh. A. Ibataev

  DOI：10.1134/s1070363213060169

  日期：2013.6

  New derivatives of cytisine and anabasine alkaloids containing benzothiazole and benzimidazole fragments were discussed. Physicochemical characteristics of the new compounds were determined. The structure of 1-(cytisin-1-yl-methyl)benzimidazole-2-thione was studied by X-ray diffraction analysis.
• Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione
  作者：A. Ya. Bespalov、T. L. Gorchakova、A. Yu. Ivanov、M. A. Kuznetsov、L. M. Kuznetsova、A. S. Pankova、L. I. Prokopenko、M. S. Avdontceva

  DOI：10.1007/s10593-014-1623-z

  日期：2015.2

  Alkylation of 1,3-dihydro-2De-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2De-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.