3-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzaldehyde | 1429498-33-8

• 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: 3-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzaldehyde
• CAS: 1429498-33-8
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: BGMBWOARWULEDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzaldehyde 、 丙二酸二乙酯 在 哌啶乙酸盐 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以60%的产率得到2-[(1-methyl-1H-benzoimidazol-2-ylmethoxy)benzylidene]malonic acid diethyl ester
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461
• 作为产物：
  描述：

  N-甲基-1,2-苯二胺 在 盐酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzaldehyde
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461