1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indole | 1352536-94-7

• 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-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indole
• CAS: 1352536-94-7
• 化学式: C₁₉H₁₉NO₅S
• 分子量: 373.43
• InChiKey: OLYUICFHAWBZGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)indole 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 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-乙酰吲哚 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 1-(4-Methoxyphenyl)sulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)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

文献信息

• A convenient iodination of indoles and derivatives
  作者：Salha Hamri、Jose Rodríguez、Joan Basset、Gérald Guillaumet、M. Dolors Pujol

  DOI：10.1016/j.tet.2012.05.053

  日期：2012.8

  We report a direct iodination of indole and derivative compounds with iodine monochloride (ICI) in the presence of Celite (R). This procedure has now been extended to the iodination of substituted indoles, azaindoles and pyrroles. The scope of this procedure is exemplified by the iodination of melatonin in 98% yield. (C) 2012 Elsevier Ltd. All rights reserved.