3,4-Bis-(4-methoxy-phenyl)-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid methyl ester | 843640-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-Bis-(4-methoxy-phenyl)-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid methyl ester
• 英文别名: methyl 3,4-bis(4-methoxyphenyl)-5-methylsulfanyl-1H-pyrrole-2-carboxylate
• CAS: 843640-98-2
• 化学式: C₂₁H₂₁NO₄S
• 分子量: 383.468
• InChiKey: HNNPOEBVMDISRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-Bis-(4-methoxy-phenyl)-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid methyl ester 在 镍 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到methyl 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: applications in the synthesis of marine pyrrole alkaloids

  摘要：

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinates with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in the presence of the Vilsmeier reagent to afford alkyl 3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. When the reaction was extended to beta-oxodithiocarboxylates derived from deoxyanision. 3,4-diarylpyrrole-2-carboxylates, the key intermediates in the synthesis of lukianol A and lamellarin Q were formed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.076
• 作为产物：
  描述：

  methyl 2-[[2,3-bis(4-methoxyphenyl)-3-oxopropanethioyl]amino]acetate 在 potassium carbonate 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 16.5h， 生成 3,4-Bis-(4-methoxy-phenyl)-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: applications in the synthesis of marine pyrrole alkaloids

  摘要：

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinates with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in the presence of the Vilsmeier reagent to afford alkyl 3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. When the reaction was extended to beta-oxodithiocarboxylates derived from deoxyanision. 3,4-diarylpyrrole-2-carboxylates, the key intermediates in the synthesis of lukianol A and lamellarin Q were formed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.076

文献信息

• Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: applications in the synthesis of marine pyrrole alkaloids
  作者：Paulson Mathew、C.V. Asokan

  DOI：10.1016/j.tetlet.2004.11.076

  日期：2005.1

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinates with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in the presence of the Vilsmeier reagent to afford alkyl 3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. When the reaction was extended to beta-oxodithiocarboxylates derived from deoxyanision. 3,4-diarylpyrrole-2-carboxylates, the key intermediates in the synthesis of lukianol A and lamellarin Q were formed. (C) 2004 Elsevier Ltd. All rights reserved.