ditert-butyl 3,3'-pyrazine-2,5-diylbis(5-methoxy-1H-indole-1-carboxylate)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ditert-butyl 3,3'-pyrazine-2,5-diylbis(5-methoxy-1H-indole-1-carboxylate)
• 化学式: C₃₂H₃₄N₄O₆
• 分子量: 570.645
• InChiKey: AWFLLNUHDRNNAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  106.7
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ditert-butyl 3,3'-pyrazine-2,5-diylbis(5-methoxy-1H-indole-1-carboxylate) 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以90%的产率得到2,5-bis(5-methoxy-1H-indole-3-yl)pyrazine
  参考文献：
  名称：

  Synthesis of Alocasin A

  摘要：

  Herein is reported a synthesis of alocasin A (1), an alkaloid component of Alocasia macrorrhiza, a herbaceous plant used in folk medicine throughout southern Asia. A double Suzuki-Miyaura cross-coupling reaction between a 3-borylindole and 2,5-dibromopyrazine was used to assemble the heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of 1, the spectroscopic data of which matched those in the isolation report of this compound.

  DOI：

  10.1021/acs.jnatprod.5b00853
• 作为产物：
  描述：

  2,5-二溴吡嗪 、 1-Boc-5-甲氧基吲哚-3-硼酸频那醇酯 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,3-二噁烷 为溶剂， 反应 18.0h， 以69%的产率得到ditert-butyl 3,3'-pyrazine-2,5-diylbis(5-methoxy-1H-indole-1-carboxylate)
  参考文献：
  名称：

  Synthesis of Alocasin A

  摘要：

  Herein is reported a synthesis of alocasin A (1), an alkaloid component of Alocasia macrorrhiza, a herbaceous plant used in folk medicine throughout southern Asia. A double Suzuki-Miyaura cross-coupling reaction between a 3-borylindole and 2,5-dibromopyrazine was used to assemble the heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of 1, the spectroscopic data of which matched those in the isolation report of this compound.

  DOI：

  10.1021/acs.jnatprod.5b00853

文献信息

• Synthesis of Alocasin A
  作者：Se Hun Kim、Jonathan Sperry

  DOI：10.1021/acs.jnatprod.5b00853

  日期：2015.12.24

  Herein is reported a synthesis of alocasin A (1), an alkaloid component of Alocasia macrorrhiza, a herbaceous plant used in folk medicine throughout southern Asia. A double Suzuki-Miyaura cross-coupling reaction between a 3-borylindole and 2,5-dibromopyrazine was used to assemble the heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of 1, the spectroscopic data of which matched those in the isolation report of this compound.