(Z)-3-(2-hydroxyethylidene)-3H-isobenzofuran-1-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-(2-hydroxyethylidene)-3H-isobenzofuran-1-one
• 英文别名: 3-(2-hydroxy-ethylidene)-3H-isobenzofuran-1-one；(3Z)-3-(2-hydroxyethylidene)-2-benzofuran-1-one
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: QMDWQZYUQCIEMB-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  2-丙炔-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58%的产率得到(Z)-3-(2-hydroxyethylidene)-3H-isobenzofuran-1-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 through palladium-catalysed heteroannulation of acetylenic compounds
  作者：Nitya G. Kundu、Manojit Pal

  DOI：10.1039/c39930000086

  日期：——

  The reaction of o-iodobenzoic acid with various acetylenic compounds in the presence of a palladium catalyst leads to phthalides [1-(3H)isobenzofuran-3-ones] as major products and isocoumarins as minor products.

  邻碘苯甲酸与各种乙炔化合物在钯催化剂的存在下反应，主要生成酞烯 [1-(3H)异苯并呋喃-3-酮]，少量生成异香豆素。
• Palladium-catalysed heteroannulation with terminal alkynes: synthesis of phthalides 1
  作者：Nitya G. Kundu、Manojit Pal、Bidisha Nandi

  DOI：10.1039/a705450e

  日期：——

  The palladium–copper-catalysed heteroannulation of o-iodobenzoic acid 3 with terminal alkynes 4–18 leads to the synthesis of (Z)-3-alkylidenephthalides 19–33 as the major products. In certain cases, the formation of isocoumarins 34–37 is also observed.

  钯-铜催化的o-碘苯甲酸3与末端炔烃4-18的杂环化反应主要合成得到(Z)-3-烷亚基苯并呋喃19-33。在某些情况下，也会观察到异香豆素34-37的形成。
• 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.
• Pd/C-mediated synthesis of (Z)-3-alkylidenephthalides of potential pharmacological interest
  作者：D. Rambabu、G. Pavan Kumar、Barange Deepak Kumar、Ravikumar Kapavarapu、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2013.03.121

  日期：2013.6

  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.