N-benzenesulfonyl-3,4-bis(4-methoxyphenyl)pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-benzenesulfonyl-3,4-bis(4-methoxyphenyl)pyrrole
• 英文别名: 3,4-bis(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrole；1-(Benzenesulfonyl)-3,4-bis(4-methoxyphenyl)pyrrole；1-(benzenesulfonyl)-3,4-bis(4-methoxyphenyl)pyrrole
• 化学式: C₂₄H₂₁NO₄S
• 分子量: 419.501
• InChiKey: QTELKZFIWIXBOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzenesulfonyl-3,4-bis(4-methoxyphenyl)pyrrole 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以77%的产率得到3,4-bis(4-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles

  摘要：

  Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.

  DOI：

  10.1021/jo501043h
• 作为产物：
  描述：

  4-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-1,2,3-triazole 、 1-甲氧基-4-(2-甲氧基乙烯基)苯 在 dirhodium tetraacetate 作用下， 以 环己烷 为溶剂， 反应 24.0h， 以45%的产率得到N-benzenesulfonyl-3,4-bis(4-methoxyphenyl)pyrrole
  参考文献：
  名称：

  Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles

  摘要：

  Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.

  DOI：

  10.1021/jo501043h

文献信息

• Palladium-catalyzed cross-coupling of N-benzenesulfonyl-3,4-dibromopyrrole and its application to the total syntheses of lamellarins O, P, Q, and R
  作者：Tsutomu Fukuda、Ei-ichi Sudo、Kozue Shimokawa、Masatomo Iwao

  DOI：10.1016/j.tet.2007.10.105

  日期：2008.1

  Palladium-catalyzed Suzuki-Miyaura Coupling of N-benzenesulfonyl-3,4-dibromopyrrole with a variety of arylboronic acids gave the corresponding 3,4-diarylpyrroles in high yields. The 3,4-differentially arylated pyrroles could also be prepared by stepwise cross-coupling approach. The total syntheses of lamellarins O, P, Q, and R have been achieved by using the cross-coupling and the directed lithiation as key reactions. (c) 2007 Elsevier Ltd. All rights reserved.
• Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles
  作者：Shanmugam Rajasekar、Pazhamalai Anbarasan

  DOI：10.1021/jo501043h

  日期：2014.9.5

  Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.