(5R,6S)-3-acetyl-5-(acetyloxy)methyl-2-methyl-1-phenyl-1,5,6,7-tetrahydropyrano[3,2-b]pyrrol-6-yl acetate | 1020540-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (5R,6S)-3-acetyl-5-(acetyloxy)methyl-2-methyl-1-phenyl-1,5,6,7-tetrahydropyrano[3,2-b]pyrrol-6-yl acetate
• 英文别名: (5R,6S)-6-acetoxy-5-(acetoxymethyl)-3-acetyl-2-methyl-1-phenyl-1,4,5,6-tetrahydropyrano[3,2-b]pyrrole；[(5R,6S)-3-acetyl-6-acetyloxy-2-methyl-1-phenyl-6,7-dihydro-5H-pyrano[3,2-b]pyrrol-5-yl]methyl acetate
• CAS: 1020540-81-1
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: XZPZJGXEXQGZKS-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[(5R,6S)-6-hydroxy-5-(hydroxymethyl)-2-methyl-1-phenyl-6,7-dihydro-5H-pyrano[3,2-b]pyrrol-3-yl]ethanone 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到(5R,6S)-3-acetyl-5-(acetyloxy)methyl-2-methyl-1-phenyl-1,5,6,7-tetrahydropyrano[3,2-b]pyrrol-6-yl acetate
  参考文献：
  名称：

  在低共熔溶剂中无酸和金属的环吡咯的合成†

  摘要：

  通过使用深度共晶溶剂（DES），通过将游离糖与烯胺偶合，从芳基胺和1,3-二酮就地生成环戊环的一种环境友好的一锅三组分合成方法。反应条件温和，不需要额外的布朗斯台德或路易斯酸催化剂。

  DOI：

  10.1039/c4ra14379e

文献信息

• Synthesis of Annulated Pyrroles: Condensation of Aldose Sugars, Arylamines, and 1,3-Diones Using TBAB
  作者：Lingaiah Nagarapu、Venkata Cheemalapati、Shuklachary Karnakanti、Rajashaker Bantu

  DOI：10.1055/s-0030-1257973

  日期：2010.10

  Readily available tetrabutylammonium bromide (TBAB, 10 mol%), in the molten state, efficiently catalyzes the reaction of a variety of in situ generated enamines, from arylamines and 1,3-ketones, with aldose sugars under solvent-free conditions. The reaction proceeds rapidly and affords the corresponding protected annulated pyrrole derivatives in good to high yields (55-78%) after acetylation. The present methodology offers advantages such as excellent yields, a simple procedure, shorter reaction times, and milder conditions.

  易于获得的熔融态四丁基溴化铵（TBAB，10 mol%）可在无溶剂条件下有效催化各种原位生成的烯胺（由芳胺和 1,3-酮）与醛糖的反应。反应进行迅速，乙酰化后以良好至高产率（55-78%）得到相应的受保护的环状吡咯衍生物。本方法具有诸如优异的产率、简单的程序、更短的反应时间和更温和的条件等优点。
• Three-Component Reaction of Aldose Sugars, Aryl Amines, and 1,3-Diones:  A Novel Synthesis of Annulated Pyrroles
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Mende Srinivas、Chitteti Divyavani、Shaik Jeelani Basha、Akella V. S. Sarma

  DOI：10.1021/jo702012w

  日期：2008.4.1

  Aldose sugars undergo smooth coupling with enamines, generated in situ from aryl amines and 1,3-diketones, in the presence of 10 mol % of InCl3 in water at 80 degrees C to furnish annulated pyrrole derivatives in relatively good to high yields. The use of InCl3, in combination with water, makes this procedure quite simple, more convenient, and environmentally friendly.