N-ethyl-2-(1H-indol-3-yl)-2-oxoacetamide | 55654-69-8

• 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-ethyl-2-(1H-indol-3-yl)-2-oxoacetamide
• 英文别名: N-ethyl-2-indol-3-yl-2-oxo-acetamide
• CAS: 55654-69-8
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD01718746
• 分子量: 216.239
• InChiKey: WHDXKEGUQIBSNS-UHFFFAOYSA-N

物化性质

• 熔点：
  203-204 °C(Solv: ethanol (64-17-5))
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-ethyl-2-(1H-indol-3-yl)-2-oxoacetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 3-[2-(乙基氨基)乙基]吲哚
  参考文献：
  名称：

  Alpha-ethyltryptamines as dual dopamine–serotonin releasers

  摘要：

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.062
• 作为产物：
  描述：

  吲哚 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 18.0h， 生成 N-ethyl-2-(1H-indol-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  Alpha-ethyltryptamines as dual dopamine–serotonin releasers

  摘要：

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.062

文献信息

• Complete and Remarkable Reversal of Chemoselectivity in [4 + 2] Cycloadditions Involving Electron-Poor Indoles as Dienophiles. Diels−Alder versus Hetero-Diels−Alder Processes
  作者：Antony Chrétien、Isabelle Chataigner、Nathalie L'Hélia、Serge R. Piettre

  DOI：10.1021/jo034719b

  日期：2003.10.1

  and 12 are now isolated in high yields, the result of two consecutive [4 + 2] processes on, first, the indole 2,3 C=C bond and, second, the 3-carbonyl unit. The possibility of using two different dienes in a tandem, sequential process is demonstrated by the preparation of tetracycle 13. Interactions between the carbonyl dienophile and Danishefsky diene yield exclusively yet another type of product, namely

  吲哚-3-羧醛1a或吲哚-3-乙二醛酸酯1b与2，3-二甲基丁二烯在热活化下的反应仅导致由吲哚2，3-碳-碳双键的参与而产生的Diels-Alder环加合物。氯化锌和高压（16 kbar）的同时使用会引起初级环加合物进一步反应，现在双环加合物11和12的收率很高，这是两个连续[4 + 2]过程的结果，首先是吲哚2,3 C = C键，其次是3-羰基单元。四环化合物13的制备证明了在串联的顺序过程中使用两种不同的二烯的可能性。羰基双亲烯与Danishefsky二烯之间的相互作用仅产生另一种类型的产物，即由顺序的[4 + 2]杂环加成，甲硅烷基烯醇醚的水解以及甲醇的损失产生的γ-二氢吡喃酮。Mukaiyama型加合物16的分离表明，至少在氯化锌催化下，可能涉及逐步机理。N，N-二取代的吲哚-3-乙二酰胺经过预期的，通常的Diels-Alder工艺，以2,3 C = C键作为亲二烯体，无论采用哪种
• KORNET M. J.; THIO A. P., J. MED. CHEM. <JMCM-AR>, 1976, 19, NO 7, 892-898
  作者：KORNET M. J.、 THIO A. P.

  DOI：——

  日期：——
• Alpha-ethyltryptamines as dual dopamine–serotonin releasers
  作者：Bruce E. Blough、Antonio Landavazo、John S. Partilla、Ann M. Decker、Kevin M. Page、Michael H. Baumann、Richard B. Rothman

  DOI：10.1016/j.bmcl.2014.07.062

  日期：2014.10

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.