ethyl 2-benzoyl-5,5-di(2-methyl-1H-indol-3-yl)pentanoate | 1418209-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-benzoyl-5,5-di(2-methyl-1H-indol-3-yl)pentanoate
• 英文别名: ethyl 2-benzoyl-5,5-bis(2-methyl-1H-indol-3-yl)pentanoate
• CAS: 1418209-97-8
• 化学式: C₃₂H₃₂N₂O₃
• 分子量: 492.618
• InChiKey: AVTQWCRMCQRCQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate 在 葡糖酸 作用下， 以 水 为溶剂， 反应 24.0h， 以76%的产率得到ethyl 2-benzoyl-5,5-di(2-methyl-1H-indol-3-yl)pentanoate
  参考文献：
  名称：

  Gluconic acid aqueous solution: a task-specific bio-based solvent for ring-opening reactions of dihydropyrans

  摘要：

  Gluconic acid aqueous solution (GAAS) that is a largely available bio-based chemical was proved to be an effective task-specific medium for ring-opening reactions of dihydropyrans. In the presence of nucleophiles, such as indoles, 1,3-cyclohexanediones, N,N-dimethylaniline, N-methylaniline, 2-naphthol, and resorcin, a series of 2-substituted 1, 3-dicarbonyl compounds were synthesized in good to excellent yields. The first example of ring-opening of oxa-Pictet-Spengler product with nucleophiles was also described. These results not only demonstrate the feasibility of using GAAS as a sustainable solvent, but also offer an effective way for the ring-opening reactions of dihydropyrans with nucleophiles. Because these reactions proceeded with excellent atom-economy in a sustainable bio-based solvent, the present method was thus characterized by many properties of green chemistry, such as green solvent, atom-economy, and utilization of bio-based chemicals. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.076

文献信息

• Gluconic acid aqueous solution: a task-specific bio-based solvent for ring-opening reactions of dihydropyrans
  作者：Jie Yang、Binghua Zhou、Minghao Li、Yanlong Gu

  DOI：10.1016/j.tet.2012.11.076

  日期：2013.1

  Gluconic acid aqueous solution (GAAS) that is a largely available bio-based chemical was proved to be an effective task-specific medium for ring-opening reactions of dihydropyrans. In the presence of nucleophiles, such as indoles, 1,3-cyclohexanediones, N,N-dimethylaniline, N-methylaniline, 2-naphthol, and resorcin, a series of 2-substituted 1, 3-dicarbonyl compounds were synthesized in good to excellent yields. The first example of ring-opening of oxa-Pictet-Spengler product with nucleophiles was also described. These results not only demonstrate the feasibility of using GAAS as a sustainable solvent, but also offer an effective way for the ring-opening reactions of dihydropyrans with nucleophiles. Because these reactions proceeded with excellent atom-economy in a sustainable bio-based solvent, the present method was thus characterized by many properties of green chemistry, such as green solvent, atom-economy, and utilization of bio-based chemicals. (C) 2012 Elsevier Ltd. All rights reserved.