ethyl 4-(4-(trifluoromethyl)benzoyl)-1H-pyrrole-2-carboxylate | 151982-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-(4-(trifluoromethyl)benzoyl)-1H-pyrrole-2-carboxylate
• 英文别名: 4-(4-Trifluoromethyl-benzoyl)-1H-pyrrole-2-carboxylic acid ethyl ester；ethyl 4-[4-(trifluoromethyl)benzoyl]-1H-pyrrole-2-carboxylate
• CAS: 151982-56-8
• 化学式: C₁₅H₁₂F₃NO₃
• 分子量: 311.26
• InChiKey: UZXKAWDAEGXTGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-(trifluoromethyl)benzoyl)-1H-pyrrole-2-carboxylate 在 盐酸 、 三乙基硅烷 、 sodium hydroxide 、 tetraphosphorus decasulfide 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 71.67h， 生成 [1,3-Dithioxo-6-(4-trifluoromethyl-benzyl)-1H-pyrrolo[1,2-c]imidazol-2-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8
• 作为产物：
  描述：

  吡咯-2-羧酸乙酯 、 4-三氟甲基苯甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到ethyl 4-(4-(trifluoromethyl)benzoyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8

文献信息

• Isocyanide-Based Multicomponent Reaction: Cascade α-Acyloxylation/Carboxamidation and [3 + 1+1] Cyclization of I(III)/S(VI)-Ylides
  作者：Dan-Ting Shen、Wen-Rong Wu、Wen-Xuan Zou、Qiong Hu、Jiaohang Wei、Mei-Zhu Bao、Xiang Liu、Shang-Shi Zhang

  DOI：10.1021/acs.orglett.4c02255

  日期：2024.7.26

  of ethyl isocyanoacetate was observed. The strategy allows for the synthesis of unsymmetrical α,α-disubstituted ketones and functionalized pyrroles with up to 99% yield and wide substrate compatibility. Notably, the procedure has been extended to the late-stage modification of drugs and natural products, offering an elegant complement to the classic Passerini reaction.

  据报道，通过类 Passerini 多组分反应，I (III) /S (VI) -叶立德、羧酸和异腈的 α-酰氧基化/甲酰胺化的无金属级联。出乎意料的是，观察到涉及I (III) /S (VI) -叶立德和两分子异氰乙酸乙酯的[3+1+1]环化。该策略可以合成不对称 α,α-二取代酮和官能化吡咯，产率高达 99%，并且具有广泛的底物兼容性。值得注意的是，该程序已扩展到药物和天然产物的后期修饰，为经典的帕塞里尼反应提供了优雅的补充。