N-benzyl-5-methoxy-1H-indole-2-carboxamide | 883051-10-3

• 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-benzyl-5-methoxy-1H-indole-2-carboxamide
• 英文别名: NSC 753792
• CAS: 883051-10-3
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: IRMIXAXYBMZVRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-5-methoxy-1H-indole-2-carboxamide 、 phenyl vinyl selenone 在 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.17h， 以76%的产率得到2-benzyl-8-methoxy-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one
  参考文献：
  名称：

  A domino approach to pyrazino- indoles and pyrroles using vinyl selenones

  摘要：

  Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2-alpha] indol-1(2H)ones and 3,4-dihydropyrrolo[1,2-alpha]pyrazin-1(2H)ones through a domino Michael/intra-molecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1H-indole-2-carboxamides or 1H-pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.10.044

文献信息

• Bicyclic compositions and methods for modulating a kinase cascade
  申请人：Hangauer, JR. David G.

  公开号：US20110136807A1

  公开（公告）日：2011-06-09

  The invention relates to compounds and methods for modulating one or more components of a kinase cascade.

  本发明涉及化合物和方法，用于调节激酶级联中的一个或多个组分。
• A transition metal-free tandem process to pyrrolopyrazino[2,3-d]pyridazine-diones
  作者：Aiping Huang、Zhi Qiao、Xinhai Zhang、Wei Yu、Qingqing Zheng、Ying Ma、Chen Ma

  DOI：10.1016/j.tet.2011.11.021

  日期：2012.1

  A transition metal-free tandem process for the synthesis of pyrrolopyrazino[2,3-d]pyridazine-diones is described. The process is an efficient construction of this tricyclic system by a one-pot coupling/Smiles rearrangement/cyclization approach. This methodology has potential applications in the synthesis of biologically and medicinally relevant compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• A domino approach to pyrazino- indoles and pyrroles using vinyl selenones
  作者：Martina Palomba、Luca Sancineto、Francesca Marini、Claudio Santi、Luana Bagnoli

  DOI：10.1016/j.tet.2018.10.044

  日期：2018.12

  Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2-alpha] indol-1(2H)ones and 3,4-dihydropyrrolo[1,2-alpha]pyrazin-1(2H)ones through a domino Michael/intra-molecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1H-indole-2-carboxamides or 1H-pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization. (C) 2018 Elsevier Ltd. All rights reserved.