4-(1H-吲哚-3-基)吡咯烷-2-酮 | 27008-33-9

• 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-(1H-吲哚-3-基)吡咯烷-2-酮
• 英文名称: 4-(1H-indol-3-yl)pyrrolidin-2-one
• CAS: 27008-33-9
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: PHCXTECEHWWWEE-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C
• 沸点：
  509.4±43.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1H-吲哚-3-基)吡咯烷-2-酮 在 水 、 sodium hydroxide 作用下， 反应 4.0h， 以63%的产率得到4-amino-3-(indol-3-yl)butanoic acid
  参考文献：
  名称：

  Synthesis and Neuropsychotropic Activity of Indole-Containing Gamma-Aminobutyric Acid Derivatives

  摘要：

  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。

  DOI：

  10.1007/s11094-018-1827-0
• 作为产物：
  描述：

  3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(1H-indol-3-yl)propionic acid 在 TEA 、 二苯基膦叠氮化物 、 N,N-二异丙基乙胺 作用下， 以 乙腈 、 叔丁醇 为溶剂， 反应 120.0h， 生成 4-(1H-吲哚-3-基)吡咯烷-2-酮
  参考文献：
  名称：

  A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives

  摘要：

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.

  DOI：

  10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

文献信息

• A Convenient Preparation of ?-Acetamido Substituted Tryptamine Derivatives
  作者：Michel Boisbrun、Elka Vassileva、Marion Raoul、Jean-Yves Laronze、Janos Sapi

  DOI：10.1007/s00706-003-0068-3

  日期：2003.12.1

  In view of finding new 5-HT6 receptor ligands various β-acetamido substituted tryptamine and N , N -dimethyltryptamine derivatives were synthesized from a common intermediate. A trimolecular condensation between indole, Meldrum ’s acid and N -phthalimidoacetaldehyde followed by careful deprotection and functional group manipulations were proposed for this purpose.

  考虑到发现新的5-HT 6受体配体，从共同的中间体合成了各种β-乙酰氨基取代的色胺和 N ， N- 二甲基色胺 衍生物。为此，提出了吲哚， Meldrum 酸和 N- 邻苯 二甲酰亚胺基乙醛之间的三分子缩合， 然后进行仔细的脱保护和官能团操作。
• 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.
• 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.
• A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives
  作者：Michel Boisbrun、Laurent Jeannin、Loïc Toupet、Jean-Yves Laronze

  DOI：10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

  日期：2000.9

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.
• 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。