| 1161079-70-4

• 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
• CAS: 1161079-70-4
• 化学式: C₂₀H₂₇FN₂O₅
• 分子量: 394.443
• InChiKey: BKPIHPYRPNFPFN-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  N',N'-(Boc)2-tryptamine 在 碳酸氢钠 、 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以73%的产率得到
  参考文献：
  名称：

  Synthetic Studies on the Fluorinated Analogs for the Putative Oxindole-Type Metabolites of 5-Halotryptamines

  摘要：

  The suitably protected precursors for direct fluorination, N(b)-Boc di-protected 5-fluorotryptamine (13), N(b)-acetyl-N(b)-Boc protected 5-halotryptamines (15a-c), were treated with Selectfluor (TM) in MeCN/water in the presence of NaHCO(3) to give the corresponding 3-fluorooxindoles 14 and 16a-c in good yields. Removal of the protecting groups of 14 and 16a-c produced (3,5-difluorooxindol-3-yl)ethylamine (8) and N-acetyl-(3-fluoro-5-halooxindol-3-yl)ethylamines (9a-c) in excellent yields, respectively. These compounds are potentially non-epimerizable analogs for the putative metabolites of 5-fluorotryptamine (6) and N(b)-acetyl-5-halotryptamines (7a-c).

  DOI：

  10.3987/com-08-s(d)70

文献信息

• A facile procedure for synthesis of 3-[2-(N,N-dialkylamino)ethyl]-3-fluorooxindoles by direct fluorination of N,N-dialkyltryptamines
  作者：Takayuki Seki、Tomoya Fujiwara、Yoshio Takeuchi

  DOI：10.1016/j.jfluchem.2010.12.014

  日期：2011.3

  A practical procedure for the synthesis of 3-fluorooxindole derivatives having basic amine moieties was developed, which involves Selectfluor™-mediated oxidative fluorination of N,N-dialkyltryptamines in the presence of Lewis acid. This procedure was applied to an antimigraine drug, rizatriptan, to afford the corresponding 3-fluorooxindole, which is a potential fluorine-containing drug candidate.

  已开发出一种合成具有碱性胺基团的3-氟羟吲哚衍生物的实用方法，该方法涉及在路易斯酸存在下，Selectfluor TM介导的N，N-二烷基色胺的氧化氟化。将该方法应用于抗偏头痛药物利扎曲普坦（rizatriptan），得到相应的3-氟羟吲哚，其是潜在的含氟药物候选物。