(Z)-3-(3-hydroxypropylidene)isobenzofuran-1(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (Z)-3-(3-hydroxypropylidene)isobenzofuran-1(3H)-one
• 英文别名: 3-(3-hydroxy-propylidene)-3H-isobenzofuran-1-one；(3Z)-3-(3-hydroxypropylidene)-2-benzofuran-1-one
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: NQZSUACQSWGMTH-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-丁炔-1-醇 、 2-溴苯甲酸 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.5h， 以55%的产率得到(Z)-3-(3-hydroxypropylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Pd/C-mediated synthesis of (Z)-3-alkylidenephthalides of potential pharmacological interest

  摘要：

  The coupling of o-bromobenzoic acid with terminal alkynes using 10% Pd/C-Et3N-CuI-PPh3 as a catalyst system leads to the synthesis of (Z)-3-alkylidenephthalides as the major product along with the traces of isocoumarin when the reaction was performed in 1,4-dioxane. The methodology afforded a range of compounds including (Z)-3-(4-(methylsulfonyl)benzylidene)isobenzofuran-1(3H)-one of potential pharmacological interest. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.121

文献信息

• Synthesis of phthalides via Pd/CNTs-catalyzed reaction of terminal alkynes and o-iodobenzoic acid under copper- and ligand-free conditions
  作者：Lei Zhou、Huan-Feng Jiang

  DOI：10.1016/j.tetlet.2007.09.170

  日期：2007.11

  A phosphine- and copper-free protocol for the synthesis of phthalides via Pd/CNTs-catalyzed tandem coupling-cyclization process has been developed. The palladium immobilized on CNTs showed high catalytic activity, and the reactions with a variety of terminal alkynes and o-iodobenoic acid proceeded smoothly to give phthalides in moderate to good yields catalyzed by 0.1% mmol Pd/CNTs. (c) 2007 Elsevier Ltd. All rights reserved.