methyl (2S)-3-(1H-indol-3-yl)-2-(methanesulfonamido)propanoate | 1351488-54-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-3-(1H-indol-3-yl)-2-(methanesulfonamido)propanoate
• CAS: 1351488-54-4
• 化学式: C₁₃H₁₆N₂O₄S
• 分子量: 296.347
• InChiKey: QFABPQCLGYRXSV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 methyl (2S)-3-(1H-indol-3-yl)-2-(methanesulfonamido)propanoate 在 三乙胺 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Copper-Catalyzed Radical Cyclization To Access 3-Hydroxypyrroloindoline: Biomimetic Synthesis of Protubonine A

  摘要：

  An unprecedented copper-catalyzed intramolecular radical cyclization was developed for the synthesis of 3-hydroxypyrroloindoline skeletons in excellent yields. The 3-hydroxyl group was introduced by trapping the radical intermediate with molecular oxygen or TEMPO. This process represents a unique radical oxidation pathway for tryptamine/tryptophan derivatives and allows a rapid biomimetic synthesis of natural product protubonine A.

  DOI：

  10.1021/ol501287x

文献信息

• Copper-Catalyzed Radical Cyclization To Access 3-Hydroxypyrroloindoline: Biomimetic Synthesis of Protubonine A
  作者：Xu Deng、Kangjiang Liang、Xiaogang Tong、Ming Ding、Dashan Li、Chengfeng Xia

  DOI：10.1021/ol501287x

  日期：2014.6.20

  An unprecedented copper-catalyzed intramolecular radical cyclization was developed for the synthesis of 3-hydroxypyrroloindoline skeletons in excellent yields. The 3-hydroxyl group was introduced by trapping the radical intermediate with molecular oxygen or TEMPO. This process represents a unique radical oxidation pathway for tryptamine/tryptophan derivatives and allows a rapid biomimetic synthesis of natural product protubonine A.