tert-butyl N-acetyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]carbamate | 1161079-77-1

• 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: tert-butyl N-acetyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]carbamate
• CAS: 1161079-77-1
• 化学式: C₁₇H₂₁FN₂O₃
• 分子量: 320.364
• InChiKey: HGXALDASWNEYIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-acetyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]carbamate 在 碳酸氢钠 、 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以75%的产率得到tert-butyl N-acetyl-N-[2-(3,5-difluoro-2-oxo-1H-indol-3-yl)ethyl]carbamate
  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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-[2-(5-fluoro-1H-indol-3-yl)ethyl]acetamide 在 四丁基硫酸氢铵 、 氯甲酸苄酯 、 sodium hydroxide 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 作用下， 以79%的产率得到tert-butyl N-acetyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]carbamate
  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

• Synthetic Studies on the Fluorinated Analogs for the Putative Oxindole-Type Metabolites of 5-Halotryptamines
  作者：Yoshio Takeuchi、Tomoya Fujiwara、Masaru Miura、Takayuki Seki

  DOI：10.3987/com-08-s(d)70

  日期：——

  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).