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

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(furan-2-ylmethyl)-3-(2-oxophenethyl)-isoindolin-1-one
• 英文别名: 2-(furan-2-ylmethyl)-3-phenacyl-3H-isoindol-1-one
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: FABQLNDXMGIDAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(furan-2-ylmethyl)-3-(2-oxophenethyl)-isoindolin-1-one 、 磷酰基乙酸三乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以23%的产率得到
  参考文献：
  名称：

  Association of Intramolecular Furan Diels-Alder Reaction and N-Acylim­­i­n­ium Alkylation for the Synthesis of Pentacyclic Precursor of Aromathecins

  摘要：

  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。

  DOI：

  10.1055/s-0029-1218300
• 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-oxophenethyl)-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

• Synthesis of 2-Benzyl-3-(2-oxo-2-phenylethyl)isoindolin-1-one Derivatives in Water under Catalyst-Free Conditions
  作者：Zongbo Xie、Zhanggao Le、Liang Jin、Hongxia Li、Jia Meng

  DOI：10.1055/a-2103-4915

  日期：2023.10

  We have developed a catalyst-free synthesis of a series of isoindolinone derivatives via a one-pot, three-component reaction in water using o-formylbenzoic acids, primary amines, and acetophenones as starting materials. An investigation of the influence of the solvent, the substrate molar ratio, the temperature, and the reaction time revealed that the reaction proceeded optimally in water at 70 °C

  我们开发了一种以邻甲酰基苯甲酸、伯胺和苯乙酮为起始原料，通过一锅三组分反应在水中无催化剂合成一系列异吲哚酮衍生物的方法。对溶剂、底物摩尔比、温度和反应时间影响的研究表明，反应在 70 °C 的水中进行了 12 小时，得到了多种异吲哚酮衍生物，产率高达 93 %。该方法具有反应条件温和、环境友好、底物范围广泛等优点。
• 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).
• 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。