3-(5-hydroxypentylidene)-3H-isobenzofuran-1-one | 1000591-11-6

• 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: 3-(5-hydroxypentylidene)-3H-isobenzofuran-1-one
• CAS: 1000591-11-6
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: UQUSUZFIQQNABO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-己炔-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 18.5h， 以68%的产率得到3-(5-hydroxypentylidene)-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

• 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.