2,3-dihydro-4,6-dinitro-1-(p-toluenesulfonyl)indole | 312513-83-0

• 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: 2,3-dihydro-4,6-dinitro-1-(p-toluenesulfonyl)indole
• 英文别名: 4,6-dinitro-1-tosylindoline；1-[(4-Methylphenyl)sulfonyl]-4,6-dinitroindoline；1-(4-methylphenyl)sulfonyl-4,6-dinitro-2,3-dihydroindole
• CAS: 312513-83-0
• 化学式: C₁₅H₁₃N₃O₆S
• mdl: MFCD01572575
• 分子量: 363.351
• InChiKey: ICMUKAOBIWFYGK-UHFFFAOYSA-N

物化性质

• 沸点：
  553.4±60.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-4,6-dinitro-1-(p-toluenesulfonyl)indole 在 氢氧化钾 、 sodium hydride 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 2.0h， 生成 1-Benzenesulfonyl-1H-indole-4,6-diamine
  参考文献：
  名称：

  Binding of amine-substituted N1-benzenesulfonylindoles at human 5-HT6 serotonin receptors

  摘要：

  An examination of several amine-substituted analogs of N-1-benzenesulfonylindoles reveals that although they bind at human 5-HT6 serotonin receptors with high affinity, they are likely to bind in a dissimilar manner. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.059
• 作为产物：
  描述：

  β-(2,4,6-trinitrophenyl)ethanol 在 吡啶 、 三氯化铁 、 一水合肼 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 2,3-dihydro-4,6-dinitro-1-(p-toluenesulfonyl)indole
  参考文献：
  名称：

  SYNTHESIS OF 4,6-DINITROINDOLE FROM 2,4,6-TRINITROTOLUENE

  摘要：

  1-R-4,6-Dinitroindoles 4-6 (R=H, Me, Ts) could be obtained from 2-picrylethanol 1 (readily available from TNT) via selective reduction of or ortho-nitro group by N2H4/FeCl3 and subsequent treatment with TsCl, to yield a key intermediate 3. This intermediate was converted to the above mentioned indoles.

  DOI：

  10.1081/scc-100104054

文献信息

• Preparation of peri-annulated indoles from polynitro compounds
  作者：Alexander V. Samet、Alexei N. Yamskov、Yuri A. Strelenko、Victor V. Semenov

  DOI：10.1016/j.tet.2009.06.074

  日期：2009.8

  A novel peri-annulated heterocyclic system of 1,2-dihydrobenz[6,7]oxepino[4,3,2-cd]indole was prepared starting from TNT via 4,6-dinitro-1-tosylindoline as a key intermediate. Base-induced CC bond shift in 1,2-dihydrobenz[6,7]oxepino[4,3,2-cd]indoles affords isomeric 2,11-dihydrobenz[6,7]oxepino[4,3,2-cd]indoles.

  一种新颖的关节周围-annulated 1,2-二氢苯并[6,7]氧杂并[4,3,2的杂环体系CD经由4,6-二硝基-1- tosylindoline]吲哚由TNT起的关键中间体。1,2-二氢苯并[6,7] oxepino [4,3,2- cd ]吲哚中的碱基诱导的C C键移位提供了异构体2,11-二氢苯并[6,7] oxepino [4,3,2- cd ]吲哚。
• ——
  作者：A. N. Yamskov

  DOI：10.1023/a:1023999915911

  日期：——

  4,6-Dinitro-1-tosylindoline prepared from trinitrotoluene undergoes base-catalyzed condensation with aromatic aldehydes. With salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde, the condensation is accompanied by intramolecular nucleophilic substitution for one of the nitro groups to give benzo- and naphthooxepino[4,3,2-cd]indoles, respectively.
• Binding of amine-substituted N1-benzenesulfonylindoles at human 5-HT6 serotonin receptors
  作者：Manik Pullagurla、Uma Siripurapu、Renata Kolanos、Mikhail L. Bondarev、Małgorzata Dukat、V. Setola、B.L. Roth、Richard A. Glennon

  DOI：10.1016/j.bmcl.2005.08.059

  日期：2005.12

  An examination of several amine-substituted analogs of N-1-benzenesulfonylindoles reveals that although they bind at human 5-HT6 serotonin receptors with high affinity, they are likely to bind in a dissimilar manner. (c) 2005 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF 4,6-DINITROINDOLE FROM 2,4,6-TRINITROTOLUENE
  作者：Alexander V. Samet、Evgenii P. Zakharov、Victor V. Semenov、A. C. Buchanan、Andrei A. Gakh

  DOI：10.1081/scc-100104054

  日期：2001.1

  1-R-4,6-Dinitroindoles 4-6 (R=H, Me, Ts) could be obtained from 2-picrylethanol 1 (readily available from TNT) via selective reduction of or ortho-nitro group by N2H4/FeCl3 and subsequent treatment with TsCl, to yield a key intermediate 3. This intermediate was converted to the above mentioned indoles.