1-[1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indol-2-yl]ethanol | 1352537-00-8

• 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: 1-[1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indol-2-yl]ethanol
• CAS: 1352537-00-8
• 化学式: C₂₁H₂₃NO₆S
• 分子量: 417.483
• InChiKey: WVRDJMDRAZPJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indol-2-yl]ethanol 在 Amberlyst-15 acid ion-exchange resin 作用下， 以 水 、 异丙醇 为溶剂， 生成 4-(4-Methoxyphenyl)sulfonyl-1,3-dimethylfuro[3,4-b]indole
  参考文献：
  名称：

  A convenient access to 1,3-disubstituted furo[3,4-b]indoles by acid ion-exchange resin-catalyzed furan formation

  摘要：

  Efficient synthesis of furo[3,4-b]indoles starting from the corresponding indole is reported. The first route involves derivatization, protection, and deprotection steps, which stretch the syntheses. The second method provides a shorter and more efficient strategy to accessing the furoindole. The innovation starts with alkylation at C-2 of the indole presenting at the C-3 position a ketone-acetal, followed by the cycloaromatization catalyzed by polymeric ion-exchange resins. The second route represents a significant improvement over other methods previously described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.022
• 作为产物：
  描述：

  3-acetyl-1-((4-methoxyphenyl)sulfonyl)indole 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1-[1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indol-2-yl]ethanol
  参考文献：
  名称：

  A convenient access to 1,3-disubstituted furo[3,4-b]indoles by acid ion-exchange resin-catalyzed furan formation

  摘要：

  Efficient synthesis of furo[3,4-b]indoles starting from the corresponding indole is reported. The first route involves derivatization, protection, and deprotection steps, which stretch the syntheses. The second method provides a shorter and more efficient strategy to accessing the furoindole. The innovation starts with alkylation at C-2 of the indole presenting at the C-3 position a ketone-acetal, followed by the cycloaromatization catalyzed by polymeric ion-exchange resins. The second route represents a significant improvement over other methods previously described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.022

文献信息

• A convenient access to 1,3-disubstituted furo[3,4-b]indoles by acid ion-exchange resin-catalyzed furan formation
  作者：Joan Basset、Manel Romero、Thaïs Serra、M. Dolors Pujol

  DOI：10.1016/j.tet.2011.10.022

  日期：2012.1

  Efficient synthesis of furo[3,4-b]indoles starting from the corresponding indole is reported. The first route involves derivatization, protection, and deprotection steps, which stretch the syntheses. The second method provides a shorter and more efficient strategy to accessing the furoindole. The innovation starts with alkylation at C-2 of the indole presenting at the C-3 position a ketone-acetal, followed by the cycloaromatization catalyzed by polymeric ion-exchange resins. The second route represents a significant improvement over other methods previously described. (C) 2011 Elsevier Ltd. All rights reserved.