N-allyl 1H-indole-2-carboxamide | 519033-25-1

• 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-allyl 1H-indole-2-carboxamide
• 英文别名: N-prop-2-enyl-1H-indole-2-carboxamide
• CAS: 519033-25-1
• 化学式: C₁₂H₁₂N₂O
• mdl: MFCD04991552
• 分子量: 200.24
• InChiKey: FFDJJUCLIWDTCS-UHFFFAOYSA-N

物化性质

• 沸点：
  471.3±28.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 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：

  N-allyl 1H-indole-2-carboxamide 在 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 77.0h， 生成 di(tert-butyl) 1-oxo-1,3-dihydroazepino[3,4-b]indole-2,10-dicarboxylate
  参考文献：
  名称：

  吲哚2-羧酸烯丙基酰胺衍生物的闭环复分解

  摘要：

  3-烯丙基或3-乙烯基吲哚-2-羧酸衍生物的闭环易位使得可以得到稠合的七元至八元内酰胺。1-烯丙基吲哚-2-羧酸高烯丙基酰胺得到九元内酰胺。还研究了1，3-二取代-2-羧酸衍生物的反应性。

  DOI：

  10.1016/s0040-4020(02)01404-7
• 作为产物：
  描述：

  吲哚-2-羧酸 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 N-allyl 1H-indole-2-carboxamide
  参考文献：
  名称：

  丙二酸酯系酰基肟的Cu（OAc）2引发的级联反应与吲哚，吲哚-2-醇和吲哚-2-羧酰胺

  摘要：

  丙二酸酯系的酰基肟与吲哚，吲哚-2-醇或吲哚-2-羧酰胺的Cu（OAc）2促进的级联反应提供了对多取代的3-吡咯啉-2-酮的便捷通道。该反应的特征在于在环化为内酰胺的同时产生两个相邻的亲电子中心。随后双加成与亲核试剂接着氧化实现亚胺SP的difunctionalization 2碳和邻近的α-SP 3碳上。

  DOI：

  10.1021/acs.orglett.9b00849

文献信息

• Uncommon intramolecular palladium-catalyzed cyclization of indole derivatives
  作者：Egle M. Beccalli、Gianluigi Broggini

  DOI：10.1016/s0040-4039(03)00116-3

  日期：2003.2

  A novel synthetic strategy based on the intramolecular palladium-catalyzed oxidative cyclization reaction, allows the formation of C–C bond and the synthesis of β-carbolinones. The reaction has been performed in the presence of catalytic amount of PdCl2(CH3CN)2 and benzoquinone as a reoxidant.

  一种基于分子内钯催化的氧化环化反应的新颖合成策略，可以形成C–C键并合成β-咔啉酮。该反应在催化量的PdCl 2（CH 3 CN）2和苯醌作为再氧化剂的存在下进行。
• <i>Exo-trig</i> selenocyclization of secondary allylic carboxamides using Woollins’ reagent: <i>en route</i> to 2,5-disubstituted selenazolines
  作者：Priyanka N. Makhal、Srinivas Reddy Dannarm、Arbaz Sujat Shaikh、Rezwan Ahmed、Shrilekha Chilvery、Lahu N. Dayare、Rajesh Sonti、Chandraiah Godugu、Venkata Rao Kaki

  DOI：10.1039/d2cc06782j

  日期：——

  We report microwave-assisted selenation and exo-trig cyclization of secondary allylic carboxamides using Woollins’ reagent, a serendipitous finding observed during an attempt to synthesize N-allylbenzoselenoamide compounds. This resulted in the first reported synthesis of 2-aryl-5-methyl selenazolines. Twenty-one diversified selenazolines and three late-stage-functionalized drug molecules were synthesized

  我们使用 Woollins 试剂报告了二级烯丙基甲酰胺的微波辅助硒化和外触发环化，这是在尝试合成N -烯丙基苯并硒酰胺化合物时观察到的偶然发现。这导致了首次报道的 2-aryl-5-methyl selenazolines 的合成。合成了 21 种多样化的硒唑啉和三种后期功能化药物分子，产率分别为 42-93% 和 25-52%，并进一步评估了它们的抗增殖活性。
• Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand
  作者：Shailesh N. Mistry、Jeremy Shonberg、Christopher J. Draper-Joyce、Carmen Klein Herenbrink、Mayako Michino、Lei Shi、Arthur Christopoulos、Ben Capuano、Peter J. Scammells、J. Robert Lane

  DOI：10.1021/acs.jmedchem.5b00585

  日期：2015.9.10

  Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)-ethyl)cyclohexyl)-1H-indole-2-carboxamide (0269652) (1) adopts a bitopic pose at one protomer of a dopamine D-2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.
• Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)₂-Promoted Intramolecular Halooxygenation of <i>N</i>-Allylcarboxamides
  作者：Gong-Qing Liu、Chun-Hua Yang、Yue-Ming Li

  DOI：10.1021/acs.joc.5b01832

  日期：2015.11.20

  A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading : to the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in good to excellent isolated yields. The 5-halomethyl products could be converted to different derivatives via conventional nucleophilic substitution methods. The reactions were carried out using easily available starting materials, and did not need harsh reaction conditions. All these features made this reaction a viable method for the construction of different oxazoline and thiazoline structures.
• Three-Component <i>cine</i>,<i>ipso</i>-Disubstitution of Nitrocoumarins
  作者：Vincent Vedovato、Anghelo J. Gangano、Ion Ghiviriga、Alexander J. Grenning

  DOI：10.1021/acs.orglett.3c03996

  日期：2024.1.26