2-(furan-2-ylmethyl)-3-(2-oxopropyl)-isoindolin-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(furan-2-ylmethyl)-3-(2-oxopropyl)-isoindolin-1-one
• 英文别名: 2-(furan-2-ylmethyl)-3-(2-oxopropyl)-3H-isoindol-1-one
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: NOACXRBBCCFGJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(furan-2-ylmethyl)isoindoline-1,3-dione 在 bismuth(lll) trifluoromethanesulfonate 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 2-(furan-2-ylmethyl)-3-(2-oxopropyl)-isoindolin-1-one
  参考文献：
  名称：

  Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst

  摘要：

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).

  DOI：

  10.1021/jo062077x

文献信息

• Metal-Free Reaction of<i>ortho</i>-Carbonylated Alkynyl-Substituted Arylaldehydes with Common Amines: Selective Access to Functionalized Isoindolinone and Indenamine Derivatives
  作者：Ziping Cao、Hongbo Zhu、Xin Meng、Jun Guan、Qiang Zhang、Laijin Tian、Xuejun Sun、Guang Chen、Jinmao You

  DOI：10.1002/chem.201603045

  日期：2016.11.14

  rearrangement to afford indenamine derivatives. In the presence of Et3N, the reaction property of small primary amines was changed, proceeding to afford 3‐hydroxylindenamine derivatives efficiently. These products contain interesting substructures that exist in many natural products and bioactive molecules. The reaction features contain the use of transition‐metal‐free catalysts, simple operation, broad

  本文中，我们描述了邻羰基化炔基取代的芳基醛与常见的伯胺的反应，该伯胺可以提供高产率的功能化异吲哚啉酮和3-羟基林丹胺产品。根据伯胺的取代基大小，选择性地利用了两个不同的反应途径，即最初的氮杂共轭物加成，然后通过氢转移进入异吲哚啉酮骨架，以及独特的氧杂共轭物加成，然后通过Petasis-Ferrier重排得到茚满衍生品。在Et 3的存在下N，改变了小的伯胺的反应性质，从而有效地提供了3-羟基林丹胺衍生物。这些产品包含存在于许多天然产品和生物活性分子中的有趣的亚结构。反应特征包括使用无过渡金属的催化剂，操作简单，底物范围广和产品多样性。
• Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst
  作者：Frédéric Pin、Sébastien Comesse、Bernard Garrigues、Štefan Marchalín、Adam Daïch

  DOI：10.1021/jo062077x

  日期：2007.2.1

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).