2.3-Dihydro-benzofuran-5-ylglyoxal

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2.3-Dihydro-benzofuran-5-ylglyoxal
• 英文别名: 2-(2,3-Dihydro-1-benzofuran-5-yl)-2-oxoacetaldehyde；2-(2,3-dihydro-1-benzofuran-5-yl)-2-oxoacetaldehyde
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: YLQOKHSSLICSAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基吲哚 、 芝麻酚 、 2.3-Dihydro-benzofuran-5-ylglyoxal 在 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 3-(6-(2,3-dihydrobenzofuran-5-yl)-[1,3]dioxolo[4,5-f]benzofuran-7-yl)-2-methyl-1H-indole
  参考文献：
  名称：

  One-pot three-component reactions of methyl ketones, phenols and a nucleophile: an expedient way to synthesize densely substituted benzofurans

  摘要：

  Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I-2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nudeophiles, such as 1,2,4-trimethoxybenzene and thiophenol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.058
• 作为产物：
  描述：

  5-乙酰基-2,3-二氢苯并[b]呋喃 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 2.3-Dihydro-benzofuran-5-ylglyoxal
  参考文献：
  名称：

  One-pot three-component reactions of methyl ketones, phenols and a nucleophile: an expedient way to synthesize densely substituted benzofurans

  摘要：

  Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I-2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nudeophiles, such as 1,2,4-trimethoxybenzene and thiophenol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.058

文献信息

• One-pot three-component reactions of methyl ketones, phenols and a nucleophile: an expedient way to synthesize densely substituted benzofurans
  作者：Cheng Cheng、Changhui Liu、Yanlong Gu

  DOI：10.1016/j.tet.2015.08.058

  日期：2015.10

  Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I-2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nudeophiles, such as 1,2,4-trimethoxybenzene and thiophenol. (C) 2015 Elsevier Ltd. All rights reserved.