2-[(1-methyl-1H-benzoimidazol-2-ylmethoxy)benzylidene]malonic acid diethyl ester | 1429498-23-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[(1-methyl-1H-benzoimidazol-2-ylmethoxy)benzylidene]malonic acid diethyl ester
• 英文别名: Diethyl 2-[[3-[(1-methylbenzimidazol-2-yl)methoxy]phenyl]methylidene]propanedioate；diethyl 2-[[3-[(1-methylbenzimidazol-2-yl)methoxy]phenyl]methylidene]propanedioate
• CAS: 1429498-23-6
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: NYKTVTSNLFECCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基-1,2-苯二胺 在 盐酸 、 哌啶乙酸盐 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 39.0h， 生成 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

文献信息

• Design and Synthesis of Benzimidazole-Linked <i>meta</i>-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities
  作者：Raman K. Verma、Rajiv Mall、Prithwish Ghosh、Vijay Kumar

  DOI：10.1080/00397911.2012.678461

  日期：2013.7.18

  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.