diethyl 2-[(3Z)-3-[[2-(1-benzylindol-3-yl)ethylamino]methylidene]-4-oxochromen-2-yl]propanedioate | 1432594-87-0

• 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: diethyl 2-[(3Z)-3-[[2-(1-benzylindol-3-yl)ethylamino]methylidene]-4-oxochromen-2-yl]propanedioate
• CAS: 1432594-87-0
• 化学式: C₃₄H₃₄N₂O₆
• 分子量: 566.654
• InChiKey: FCWGYHALFBHAOB-NHFJDJAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(1-苄基-1H-吲哚-3-基)-乙胺 、 在 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 diethyl 2-[(3Z)-3-[[2-(1-benzylindol-3-yl)ethylamino]methylidene]-4-oxochromen-2-yl]propanedioate 、 ethyl 1-(2-(1-benzyl-1H-indol-3-yl)ethyl)-5-(2-hydroxybenzoyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  A versatile domino process for the synthesis of substituted 3-aminomethylene-chromanones and 2-pyridones catalyzed by CsF

  摘要：

  The addition of various primary amines onto 3-alpha,beta-unsaturated diester chromone derivative was studied under mild conditions. Basically, this reaction provided 2-pyridone-based compounds through an interesting domino 'Addition/Ring Opening/Ring Closure' process (ARORC). In this study, aniline and tryptamine series exhibited different reactivity profiles leading unexpectedly to 3-aminomethylene chromanones with or without the 2-pyridone derivatives. This constitutes the first description and study of 3-aminomethylene chromanone formation that is supposed to follow a domino process combining 'Addition/Ring Opening/Ring Closure by Oxa-Michael addition' (ARORCOM). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.096

文献信息

• A versatile domino process for the synthesis of substituted 3-aminomethylene-chromanones and 2-pyridones catalyzed by CsF
  作者：Catalin Pintiala、Ata Martin Lawson、Sébastien Comesse、Adam Daïch

  DOI：10.1016/j.tetlet.2013.03.096

  日期：2013.5

  The addition of various primary amines onto 3-alpha,beta-unsaturated diester chromone derivative was studied under mild conditions. Basically, this reaction provided 2-pyridone-based compounds through an interesting domino 'Addition/Ring Opening/Ring Closure' process (ARORC). In this study, aniline and tryptamine series exhibited different reactivity profiles leading unexpectedly to 3-aminomethylene chromanones with or without the 2-pyridone derivatives. This constitutes the first description and study of 3-aminomethylene chromanone formation that is supposed to follow a domino process combining 'Addition/Ring Opening/Ring Closure by Oxa-Michael addition' (ARORCOM). (C) 2013 Elsevier Ltd. All rights reserved.