[(E)-2,3-Bis-(4-methoxy-phenyl)-1-methylsulfanyl-3-oxo-propenylamino]-acetic acid methyl ester | 843640-96-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [(E)-2,3-Bis-(4-methoxy-phenyl)-1-methylsulfanyl-3-oxo-propenylamino]-acetic acid methyl ester
• 英文别名: methyl 2-[[(E)-2,3-bis(4-methoxyphenyl)-1-methylsulfanyl-3-oxoprop-1-enyl]amino]acetate
• CAS: 843640-96-0
• 化学式: C₂₁H₂₃NO₅S
• 分子量: 401.483
• InChiKey: AIALQVMNUGUAPP-XUTLUUPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(E)-2,3-Bis-(4-methoxy-phenyl)-1-methylsulfanyl-3-oxo-propenylamino]-acetic acid methyl ester 在 镍 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 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 2,3-bis(4-methoxyphenyl)-3-oxopropanedithioate 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.5h， 生成 [(E)-2,3-Bis-(4-methoxy-phenyl)-1-methylsulfanyl-3-oxo-propenylamino]-acetic 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.