2-[(3,4-dimethoxyphenyl)(4,5-dimethoxy-2-(2-hydroxyethyl)phenyl)methyl]-1H-pyrrole | 1418210-13-5

• 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-[(3,4-dimethoxyphenyl)(4,5-dimethoxy-2-(2-hydroxyethyl)phenyl)methyl]-1H-pyrrole
• 英文别名: 2-[2-[(3,4-dimethoxyphenyl)-(1H-pyrrol-2-yl)methyl]-4,5-dimethoxyphenyl]ethanol
• CAS: 1418210-13-5
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: ZMGRHWCKKIPZOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吡咯 、 1-(3,4-dimethoxyphenyl)-6,7-dimethoxyisochroman 在 葡糖酸 作用下， 以 水 为溶剂， 反应 11.0h， 以46%的产率得到2-[(3,4-dimethoxyphenyl)(4,5-dimethoxy-2-(2-hydroxyethyl)phenyl)methyl]-1H-pyrrole
  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.