2-(5-nitro-1H-inden-3-yl)-1-(piperidin-1-yl)ethanone | 1119518-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-(5-nitro-1H-inden-3-yl)-1-(piperidin-1-yl)ethanone
• 英文别名: 1-[(5-nitro-1H-inden-3-yl)acetyl]piperidine；2-(6-nitro-3H-inden-1-yl)-1-piperidin-1-ylethanone
• CAS: 1119518-71-6
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: UYJLVPNTYFYVAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C
• 沸点：
  482.5±45.0 °C(predicted)
• 密度：
  1.264±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-nitro-1H-inden-3-yl)-1-(piperidin-1-yl)ethanone 在 alane N,N-dimethylethylamine complex 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Indene-Based Scaffolds. 2. An Indole−Indene Switch: Discovery of Novel Indenylsulfonamides as 5-HT₆ Serotonin Receptor Agonists

  摘要：

  Scaffold selection involving an indole-to-indene core change led to the discovery of a series of indenylsulfonamides that act as 5-HT6 serotonin receptor agonists. The variety of the targeted ligands and their synthetic complexity required multistep synthetic approaches. The novel indenylsulfonamides exhibited variable binding affinities for the 5-HT6 receptor, and the in vitro primary binding profiles of the preferred compounds revealed them to be 5-HT6 receptor agonists with K-i values >= 4.5 nM. The structural changes responsible for enhancing the affinities indicated a directing effect modulated by the nature of the indene core, the substitution at the aminoethyl side chain, and especially by the aryl(heteroaryl)sulfonyl group on the indene 5-position. A representative of the family, the N-(inden-5-yl)imidazothiazole-5-sulfonamide (43), exhibited a high affinity and functioned as a potent full agonist for the 5-HT6 receptor (K-i = 4.5 nM, EC50 = 0.9 nM, E-max = 98%).

  DOI：

  10.1021/jm8009469
• 作为产物：
  描述：

  6-硝基-1-茚满酮 在 磺酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(5-nitro-1H-inden-3-yl)-1-(piperidin-1-yl)ethanone
  参考文献：
  名称：

  多功能茚的合成方法。

  摘要：

  具有至少两个不同官能团的多功能茚的合成尚未得到广泛探索。在具有两个不同官能团的 3,5-二取代茚（例如 [3-（氨基乙基）茚-5-基）] 胺的合理合成路线中，合理的途径涉及（5-硝基-3-茚基）乙酰胺作为关键中间体。虽然可以应用几种多步合成方法来获得这些高级中间体，但我们在本文中描述了它们通过 5-硝基茚满-1-酮与 N,N-二取代乙酰胺的锂盐之间的羟醛型反应制备，然后立即用酸。这种经典的缩合过程虽然具有明显的直接性，但既不简单也不平凡，它允许有效地进入各种基于茚的分子模块，

  DOI：

  10.3762/bjoc.7.204

文献信息

• Synthetic approaches to multifunctional indenes
  作者：Neus Mesquida、Sara López-Pérez、Immaculada Dinarès、Ermitas Alcalde

  DOI：10.3762/bjoc.7.204

  日期：——

  The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3-indenyl)acetamides as key intermediates. Although several multistep synthetic

  具有至少两个不同官能团的多功能茚的合成尚未得到广泛探索。在具有两个不同官能团的 3,5-二取代茚（例如 [3-（氨基乙基）茚-5-基）] 胺的合理合成路线中，合理的途径涉及（5-硝基-3-茚基）乙酰胺作为关键中间体。虽然可以应用几种多步合成方法来获得这些高级中间体，但我们在本文中描述了它们通过 5-硝基茚满-1-酮与 N,N-二取代乙酰胺的锂盐之间的羟醛型反应制备，然后立即用酸。这种经典的缩合过程虽然具有明显的直接性，但既不简单也不平凡，它允许有效地进入各种基于茚的分子模块，
• Indene-Based Scaffolds. 2. An Indole−Indene Switch: Discovery of Novel Indenylsulfonamides as 5-HT₆ Serotonin Receptor Agonists
  作者：Ermitas Alcalde、Neus Mesquida、Sara López-Pérez、Jordi Frigola、Ramon Mercè

  DOI：10.1021/jm8009469

  日期：2009.2.12

  Scaffold selection involving an indole-to-indene core change led to the discovery of a series of indenylsulfonamides that act as 5-HT6 serotonin receptor agonists. The variety of the targeted ligands and their synthetic complexity required multistep synthetic approaches. The novel indenylsulfonamides exhibited variable binding affinities for the 5-HT6 receptor, and the in vitro primary binding profiles of the preferred compounds revealed them to be 5-HT6 receptor agonists with K-i values >= 4.5 nM. The structural changes responsible for enhancing the affinities indicated a directing effect modulated by the nature of the indene core, the substitution at the aminoethyl side chain, and especially by the aryl(heteroaryl)sulfonyl group on the indene 5-position. A representative of the family, the N-(inden-5-yl)imidazothiazole-5-sulfonamide (43), exhibited a high affinity and functioned as a potent full agonist for the 5-HT6 receptor (K-i = 4.5 nM, EC50 = 0.9 nM, E-max = 98%).