1-(1,3-Benzodioxol-5-ylmethyl)-5-oxo-2-thiophen-2-ylpyrrolidine-3-carboxylic acid | 1311589-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(1,3-Benzodioxol-5-ylmethyl)-5-oxo-2-thiophen-2-ylpyrrolidine-3-carboxylic acid
• CAS: 1311589-28-2
• 化学式: C₁₇H₁₅NO₅S
• 分子量: 345.376
• InChiKey: YIFLHLKOCNBVLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁二酸酐 、 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 1-(1,3-Benzodioxol-5-ylmethyl)-5-oxo-2-thiophen-2-ylpyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides

  摘要：

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.

  DOI：

  10.1021/co4001277

文献信息

• Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Dmitry S. Granat、Eugeniy N. Ostapchuk、Dmitriy V. Kryvoruchko、Oleksandr O. Grygorenko

  DOI：10.1021/co4001277

  日期：2014.3.10

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.