cis-4,5-dihydro-1-(4'-methylphenylsulfonyl)-2,4,5-trimethylcyclopenta[b]pyrrol-6(1H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-4,5-dihydro-1-(4'-methylphenylsulfonyl)-2,4,5-trimethylcyclopenta[b]pyrrol-6(1H)-one
• 英文别名: (4R,5S)-2,4,5-trimethyl-1-(4-methylphenyl)sulfonyl-4,5-dihydrocyclopenta[b]pyrrol-6-one
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: VLHKJWOJQBGFAX-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  惕格酸 、 2-methyl-N-tosylpyrrole 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 trans-4,5-dihydro-1-(4'-methylphenylsulfonyl)-2,4,5-trimethylcyclopenta[b]pyrrol-6(1H)-one 、 cis-4,5-dihydro-1-(4'-methylphenylsulfonyl)-2,4,5-trimethylcyclopenta[b]pyrrol-6(1H)-one
  参考文献：
  名称：

  The First Examples of Nazarov Cyclizations Leading to Annulated Pyrroles

  摘要：

  Reactions between alpha-substituted unsaturated carboxylic acids 20 and N-tosylpyrroles [14, 23] in the presence of trifluoroacetic anhydride result in smooth alpha-acylation of the pyrrole, followed by Nazarov cyclization to give 50-80% yields of cyclopenta[b]pyrroles. The presence of an alpha-substituent in the unsaturated acid appears to be mandatory.

  DOI：

  10.1021/ol052683z

文献信息

• The First Examples of Nazarov Cyclizations Leading to Annulated Pyrroles
  作者：Chuanjun Song、David W. Knight、Maria A. Whatton

  DOI：10.1021/ol052683z

  日期：2006.1.1

  Reactions between alpha-substituted unsaturated carboxylic acids 20 and N-tosylpyrroles [14, 23] in the presence of trifluoroacetic anhydride result in smooth alpha-acylation of the pyrrole, followed by Nazarov cyclization to give 50-80% yields of cyclopenta[b]pyrroles. The presence of an alpha-substituent in the unsaturated acid appears to be mandatory.