dimethyl 3-[1-(benzenesulfonyl)indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylate | 1207172-98-2

• 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: dimethyl 3-[1-(benzenesulfonyl)indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylate
• CAS: 1207172-98-2
• 化学式: C₃₀H₂₃N₃O₆S
• 分子量: 553.595
• InChiKey: CLTVKBNEBSECOD-UHFFFAOYSA-N

物化性质

• 沸点：
  851.7±75.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 3-[1-(benzenesulfonyl)indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylate 在 氯化铵 、 magnesium 作用下， 以 甲醇 为溶剂， 以93%的产率得到lycogarubin C
  参考文献：
  名称：

  Total synthesis of lycogarubin C utilizing the Kornfeld–Boger ring contraction

  摘要：

  An efficient synthesis of lycogarubin C (3) was completed in seven steps from the known 1-(phenylsulfonyl)indole-3-carbaldehyde in 30% overall yield, via a Diels-Alder reaction between (Z)-1,2-di(1H-indol-3-yl)ethene 9b and dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (7), followed by a Kornfeld-Boger ring contraction to form the pyrrole ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.085
• 作为产物：
  描述：

  、 1,2,4,5-四嗪-3,6-二羧酸二甲酯 在 锌 作用下， 以 甲苯 、 溶剂黄146 为溶剂， 以21%的产率得到dimethyl 3-[1-(benzenesulfonyl)indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylate
  参考文献：
  名称：

  Total synthesis of lycogarubin C utilizing the Kornfeld–Boger ring contraction

  摘要：

  An efficient synthesis of lycogarubin C (3) was completed in seven steps from the known 1-(phenylsulfonyl)indole-3-carbaldehyde in 30% overall yield, via a Diels-Alder reaction between (Z)-1,2-di(1H-indol-3-yl)ethene 9b and dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (7), followed by a Kornfeld-Boger ring contraction to form the pyrrole ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.085

文献信息

• Total synthesis of lycogarubin C utilizing the Kornfeld–Boger ring contraction
  作者：Liangfeng Fu、Gordon W. Gribble

  DOI：10.1016/j.tetlet.2009.11.085

  日期：2010.1

  An efficient synthesis of lycogarubin C (3) was completed in seven steps from the known 1-(phenylsulfonyl)indole-3-carbaldehyde in 30% overall yield, via a Diels-Alder reaction between (Z)-1,2-di(1H-indol-3-yl)ethene 9b and dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (7), followed by a Kornfeld-Boger ring contraction to form the pyrrole ring. (C) 2009 Elsevier Ltd. All rights reserved.