2-{3-[3-(Phenylsulfonyl)-1H-indol-1-yl]propyl}isoindole-1,3-dione | 633291-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{3-[3-(Phenylsulfonyl)-1H-indol-1-yl]propyl}isoindole-1,3-dione
• 英文别名: 3-phenylsulfonyl-1-(3-phthalimidopropyl)indole；2-[3-[3-(benzenesulfonyl)indol-1-yl]propyl]isoindole-1,3-dione
• CAS: 633291-63-1
• 化学式: C₂₅H₂₀N₂O₄S
• 分子量: 444.511
• InChiKey: XXFXFXQYKZSFER-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C(Solv: ethanol (64-17-5))
• 沸点：
  681.3±35.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{3-[3-(Phenylsulfonyl)-1H-indol-1-yl]propyl}isoindole-1,3-dione 在 Raney nickel 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以89%的产率得到2-[3-(1H-indol-1-yl)propyl]hexahydro-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

  摘要：

  The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.

  DOI：

  10.1007/s10593-010-0504-3
• 作为产物：
  描述：

  3-phenylthioindole 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-{3-[3-(Phenylsulfonyl)-1H-indol-1-yl]propyl}isoindole-1,3-dione
  参考文献：
  名称：

  2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

  摘要：

  The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.

  DOI：

  10.1007/s10593-010-0504-3

文献信息

• 1-(AMINOALKYL)-3-SULFONYLINDOLE AND-INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS
  申请人：Wyeth

  公开号：US20030232828A1

  公开（公告）日：2003-12-18

  The present invention provides compounds of formula I and the use thereof for the treatment of central nervous system disorders related to or affected by the 5-HT6 receptor. 1

  本发明提供了化合物I的公式以及其用于治疗与5-HT6受体相关或受其影响的中枢神经系统疾病的用途。
• 1-(AMINOALKYL)-3-SULFONYLINDOLE AND -INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS
  申请人：Wyeth

  公开号：EP1509501A1

  公开（公告）日：2005-03-02
• US6727246B2
  申请人：——

  公开号：US6727246B2

  公开（公告）日：2004-04-27
• [EN] 1-(AMINOALKYL)-3-SULFONYLINDOLE AND -INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS<br/>[FR] DERIVES DE 1-(AMINOALKYL)-3-SULFONYLINDOLE ET -INDAZOLE COMME LIGANDS 5-HYDROXYTRYPTAMINE-6
  申请人：WYETH CORP

  公开号：WO2003101962A1

  公开（公告）日：2003-12-11

  The present invention provides compounds of formula (I) and the use thereof for the treatment of central nervous system disorders related to or affected by the 5-HT6 receptor.
• 2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions
  作者：A. V. Karchava、I. S. Shuleva、A. A. Ovcharenko、M. A. Yurovskaya

  DOI：10.1007/s10593-010-0504-3

  日期：2010.7

  The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.