N^b,N^b-di-(tert-butoxycarbonyl)-5-fluorotryptamine | 1161079-74-8

• 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: N^b,N^b-di-(tert-butoxycarbonyl)-5-fluorotryptamine
• 英文别名: tert-butyl N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 1161079-74-8
• 化学式: C₂₀H₂₇FN₂O₄
• 分子量: 378.444
• InChiKey: BVLBLBNNIXUUDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^b,N^b-di-(tert-butoxycarbonyl)-5-fluorotryptamine 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tert-butyl N-[2-(3,5-difluoro-2-oxo-1H-indol-3-yl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]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：

  2-碘-4-氟苯胺 、 4-[N,N-bis(tert-butoxycarbonyl)butyraldehyde 在 三乙烯二胺 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以56%的产率得到N^b,N^b-di-(tert-butoxycarbonyl)-5-fluorotryptamine
  参考文献：
  名称：

  Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin

  摘要：

  A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.050

文献信息

• Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin
  作者：Chunmei Hu、Hua Qin、Yuxin Cui、Yanxing Jia

  DOI：10.1016/j.tet.2009.09.050

  日期：2009.11

  A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described. (C) 2009 Elsevier Ltd. All rights reserved.
• 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).