N-(4-methoxybenzenesulfonyl)indole-2-carboxylic acid | 334701-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(4-methoxybenzenesulfonyl)indole-2-carboxylic acid
• 英文别名: N-(p-Methoxyphenylsulfonyl)indole-2-carboxylic acid；1-(4-Methoxyphenyl)sulfonylindole-2-carboxylic acid
• CAS: 334701-11-0
• 化学式: C₁₆H₁₃NO₅S
• 分子量: 331.349
• InChiKey: MZESSJKCCJQSRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzenesulfonyl)indole-2-carboxylic acid 在 manganese(IV) oxide 、 氯化亚砜 、 四甲基乙二胺 、 叔丁基锂 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 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：

  吲哚-2-羧酸甲酯 在 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-methoxybenzenesulfonyl)indole-2-carboxylic acid
  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

• Cyclodimerization of indol-2-ylacetylenes. An example of intermolecular enyne–alkyne cycloaddition
  作者：Daniele Passarella、Alessandra Giardini、Marisa Martinelli、Alessandra Silvani

  DOI：10.1039/b009154p

  日期：——

  Cyclodimerization of methyl 3-(indol-2-yl)propiolate 1 and 2-(indol-2-yl)-1-(phenylsulfonyl)acetylene 2 proceeds through an enyne–alkyne cycloaddition to give 4-(indol-2-yl)carbazoles.

  3-(吲哚-2-基)丙炔酸甲酯 1 和 2-(吲哚-2-基)-1-(苯磺酰基)乙炔 2 通过烯炔烃环化反应生成 4-(吲哚-2-基)咔唑。
• 1-BENZENESULFONYL-1H-INDOLE DERIVATIVES AS INHIBITORS OF CCR9 ACTIVITY
  申请人：Novartis AG

  公开号：EP2118060B1

  公开（公告）日：2010-10-06
• 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.