4-(1-甲基吲哚-3-基)吡咯烷-2-酮 | 88221-20-9

• 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
• 中文名称: 4-(1-甲基吲哚-3-基)吡咯烷-2-酮
• 英文名称: (methyl-1 indol-3 yl)-4 pyrrolidinone-2
• 英文别名: 4-(1-methylindol-3-yl)-2-pyrrolidone；3-(1-methylindol-3-yl)-2-pyrrolidone；4-(1-methyl-1H-indol-3-yl)pyrrolidin-2-one；4-(1-methylindol-3-yl)pyrrolidin-2-one
• CAS: 88221-20-9
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: RFFWGNLJTXLSNP-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C(Solv: ethanol (64-17-5))
• 沸点：
  482.0±38.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1-甲基吲哚-3-基)吡咯烷-2-酮 在 氨 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 、 苯 为溶剂， 反应 30.0h， 生成 2-[4-(1-methylindol-3-yl)-2-pyrrolidon-1-yl]acetamide
  参考文献：
  名称：

  Synthesis and Structure of 2-(4-Heteryl-2-pyrrolidon-1-yl)acetamides

  摘要：

  1-Alkoxycarbonylmethyl-4-heteryl-2-pyrrolidones were synthesized by alkylation of 4-heteryl-2-pyrrolidones. 2-(4-Heteryl-2-pyrrolidon-1-yl)acetamides were prepared through the reaction of N-esters with ammonia. The resulting acetamides of 2-pyrrolidones exhibit nootropic properties, antiarrhythmic and antiischemic activity.

  DOI：

  10.1134/s1070363218070046
• 作为产物：
  描述：

  4-(1-methylindol-3-yl)-3-hydroxycarbonyl-2-pyrrolidone 反应 1.5h， 以91%的产率得到4-(1-甲基吲哚-3-基)吡咯烷-2-酮
  参考文献：
  名称：

  Maillard; Langlois; Vo Van, European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 353 - 358

  摘要：

  DOI：

文献信息

• Synthesis and Neuropsychotropic Activity of Indole-Containing Gamma-Aminobutyric Acid Derivatives
  作者：V. M. Berestovitskaya、O. S. Vasil’eva、E. S. Ostroglyadov、S. M. Aleksandrova、I. N. Tyurenkov、O. V. Merkushenkova、V. V. Bagmetova

  DOI：10.1007/s11094-018-1827-0

  日期：2018.8

  A series of indole-containing γ-aminobutyric acids (GABA) were synthesized via alkaline hydrolysis of 4-(indol-3-yl)-2-pyrrolidones. Their structures were confirmed by IR, PMR, and 13C NMR spectroscopy. Studies of the pharmacological properties of 4-amino-3-indolylbutanoic acids (GABA derivatives) showed that they possessed neuropsychotropic activity, the spectrum of which depended on the acid molecular structure. Nootropic properties prevailed for 4-amino-3-(indol-3-yl)butanoic acid; anxiolytic activity, for 4-amino-3-(1-benzylindol-3-yl)butanoic acid.

  一系列含吲哚的γ-氨基丁酸（GABA）通过对4-(吲哚-3-基)-2-吡咯烷酮的碱性水解合成。它们的结构通过红外光谱（IR）、质子核磁共振（PMR）和碳-13核磁共振（13C NMR）得到了确认。对4-氨基-3-吲哚基丁酸（GABA衍生物）药理特性的研究表明，它们具有神经精神药理活性，其谱系依赖于酸的分子结构。4-氨基-3-(吲哚-3-基)丁酸的认知促进特性较为突出；而4-氨基-3-(1-苯基吲哚-3-基)丁酸则表现出较强的抗焦虑活性。
• Indole-containing derivatives of α-pyrrolidone: Synthesis and structure
  作者：E. S. Ostroglyadov、O. S. Vasil’eva、S. M. Aleksandrova、V. V. Pelipko、V. M. Berestovitskaya、I. N. Tyurenkov、V. V. Bagmetova

  DOI：10.1134/s1070363215080095

  日期：2015.8

  4-(Indol-3-yl)-2-pyrrolidone and its derivatives have been synthesized via sequential hydrogenation of indole-containing esters of 4-nitrobutanoic acid, alkaline hydrolysis of the resulting 3-methoxycarbonyl-2- pyrrolidones, and decarboxylation of the isolated 2-pyrrolidone-3-carboxylic acids. Structures of the products have been confirmed by IR, H-1 NMR, H-1-C-13 HMQC, and H-1-H-1 NOESY spectroscopy methods.
• MAILLARD, J.;LANGLOIS, M.;TRI, VO, VAN;GUILLONNEAU, C.;LEGEA, J.;BENHARKA+, EUR. J. MED. CHEM., 1983, 18, N 4, 353-358
  作者：MAILLARD, J.、LANGLOIS, M.、TRI, VO, VAN、GUILLONNEAU, C.、LEGEA, J.、BENHARKA+

  DOI：——

  日期：——
• Synthesis and Structure of 2-(4-Heteryl-2-pyrrolidon-1-yl)acetamides
  作者：O. S. Vasil’eva、E. S. Ostroglyadov、N. V. Gorodnicheva、S. V. Makarenko、I. N. Tyurenkov、V. N. Perfilova、S. M. Aleksandrova

  DOI：10.1134/s1070363218070046

  日期：2018.7

  1-Alkoxycarbonylmethyl-4-heteryl-2-pyrrolidones were synthesized by alkylation of 4-heteryl-2-pyrrolidones. 2-(4-Heteryl-2-pyrrolidon-1-yl)acetamides were prepared through the reaction of N-esters with ammonia. The resulting acetamides of 2-pyrrolidones exhibit nootropic properties, antiarrhythmic and antiischemic activity.
• Maillard; Langlois; Vo Van, European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 353 - 358
  作者：Maillard、Langlois、Vo Van、et al.

  DOI：——

  日期：——