3-acetoxy-2-(furan-2-ylmethyl)-isoindolin-1-one | 929206-58-6

• 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: 3-acetoxy-2-(furan-2-ylmethyl)-isoindolin-1-one
• 英文别名: [2-(furan-2-ylmethyl)-3-oxo-1H-isoindol-1-yl] acetate
• CAS: 929206-58-6
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: AAMDKJNFNFDLBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxy-2-(furan-2-ylmethyl)-isoindolin-1-one 、 2-(三甲基硅氧基)丙烯 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 以71%的产率得到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
• 作为产物：
  描述：

  2-(furan-2-ylmethyl)isoindoline-1,3-dione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-acetoxy-2-(furan-2-ylmethyl)-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

• Association of Intramolecular Furan Diels-Alder Reaction and N-Acylim­­i­n­ium Alkylation for the Synthesis of Pentacyclic Precursor of Aromathecins
  作者：Adam Daïch、Frédéric Pin、Sébastien Comesse

  DOI：10.1055/s-0029-1218300

  日期：2009.12

  A new approach for the synthesis of isoindoloquinoline and aromathecin templates is presented. These were obtained in a few steps starting from inexpensive reagents by two different strategies. The key step for both sequences was the IMFDA reaction, leading diastereoselectively to the formation of the unsaturated DE ring system of the expected alkaloid skeletons.

  本文介绍了一种合成异吲哚喹啉和芳香霉素模板的新方法。从廉价的试剂开始，通过两种不同的策略，只需几步就能获得这些试剂。两个序列的关键步骤都是 IMFDA 反应，该反应导致非对映选择性地形成预期生物碱骨架的不饱和 DE 环系统。