3-(4-methoxyphenyl)-4-iodo-1H-isochromen-1-one | 1159371-58-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(4-methoxyphenyl)-4-iodo-1H-isochromen-1-one
• 英文别名: 4-Iodo-3-(4-methoxyphenyl)isochromen-1-one
• CAS: 1159371-58-0
• 化学式: C₁₆H₁₁IO₃
• 分子量: 378.166
• InChiKey: DBEIVCIEHCTABV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((4-methoxyphenyl)ethynyl)benzoic acid 在 碘 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 3-(4-methoxyphenyl)-4-iodo-1H-isochromen-1-one
  参考文献：
  名称：

  Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donor in presence of thioglycosides

  摘要：

  A novel and high yielding glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and iodine as promoter is described. The donors are stable and can be chemoselectively activated in the presence of thioethyl and thiophenyl glycosides. The application of this methodology in one-pot consecutive glycosylation reaction is described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.101

文献信息

• TBAI-mediated regioselective 5-exo-dig iodinative oxocyclization of 2-alkynylbenzamides for the synthesis of isobenzofuran-1-imines and isobenzofurans
  作者：Yan-Hua Wang、Jin-Biao Liu、Banlai Ouyang、Hongwei Zhou、Guanyinsheng Qiu

  DOI：10.1016/j.tet.2018.07.013

  日期：2018.8

  functionalization is an important transformation method for the synthesis of a wide variety of organic products. In this work, a regioselective TBAI-mediated oxidative 5-exo-dig iodo-oxycyclization of 2-alkynylbenzamide is used for the synthesis of various isobenzofuran derivatives with excellent functional group tolerance and high reaction efficiency. We hypothesized that using water in a mixed solvent could change

  基于炔烃的区域选择性官能化是合成多种有机产物的重要转化方法。在这项工作中，区域选择性TBAI介导的2-炔基苯甲酰胺的氧化5-外切-碘-氧环化反应用于合成具有优异的官能团耐受性和高反应效率的各种异苯并呋喃衍生物。我们假设在混合溶剂中使用水可以改变反应路径并实现高反应区域选择性。此外，通过酞菁-1（2 H）-1和芳基取代的异苯并呋喃的合成证明了所开发方法的应用。
• Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach
  作者：Marine Peuchmaur、Vincent Lisowski、Céline Gandreuil、Ludovic T. Maillard、Jean Martinez、Jean-François Hernandez

  DOI：10.1021/jo900281a

  日期：2009.6.5

  A straightforward and traceless solid-phase methodology was developed for the synthesis of isocournarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.