1-methyl-4-(phenyl-sulfonyl)-1H-furo[3,4-b]indol-3(4H)-one | 1239864-83-5

• 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: 1-methyl-4-(phenyl-sulfonyl)-1H-furo[3,4-b]indol-3(4H)-one
• 英文别名: 4-(benzenesulfonyl)-1-methyl-1H-furo[3,4-b]indol-3-one
• CAS: 1239864-83-5
• 化学式: C₁₇H₁₃NO₄S
• 分子量: 327.361
• InChiKey: XZTQXLNPKHUHNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  574.2±60.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(phenyl-sulfonyl)-1H-furo[3,4-b]indol-3(4H)-one 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[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：

  1-(苯磺酰基)-1H-吲哚-2-羧酸 在 manganese(IV) oxide 、 氯化亚砜 、 四甲基乙二胺 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 1-methyl-4-(phenyl-sulfonyl)-1H-furo[3,4-b]indol-3(4H)-one
  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

• Desulfonylation of Indoles and 7-Azaindoles Using Sodium tert-Butoxide
  作者：Marie-Claude Viaud-Massuard、Charlotte Chaulet、Cécile Croix、Joan Basset、Maria-Dolores Pujol

  DOI：10.1055/s-0029-1219918

  日期：2010.6

  A mild method for the desulfonylation of N-indoles and N-azaindoles is described. Deprotection is carried out under basic conditions, using sodium tert-butoxide in dioxane. Several functionalized indoles and 7-azaindoles were efficiently deprotected by this method, which is mild enough to be used to deprotect compounds including functions that are known to be sensitive to acidic or basic conditions.

  本文介绍了一种温和的 N-吲哚和 N-氮杂吲哚脱磺化方法。脱保护是在二噁烷中使用叔丁醇钠在碱性条件下进行的。这种方法非常温和，可用于对包括已知对酸性或碱性条件敏感的功能在内的化合物进行脱保护。