5H-thiopyrano[2,3-b:6,5-b']diindole | 339306-72-8

• 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: 5H-thiopyrano[2,3-b:6,5-b']diindole
• 英文别名: 12-Thia-10,14-diazapentacyclo[11.7.0.03,11.04,9.015,20]icosa-1(13),2,4,6,8,10,15,17,19-nonaene
• CAS: 339306-72-8
• 化学式: C₁₇H₁₀N₂S
• 分子量: 274.346
• InChiKey: QIVQYEJQPXVKLA-UHFFFAOYSA-N

物化性质

• 沸点：
  499.6±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H-thiopyrano[2,3-b:6,5-b']diindole 、 碘甲烷 生成 14-Methyl-12-thia-10,14-diazapentacyclo[11.7.0.03,11.04,9.015,20]icosa-1(13),2,4,6,8,10,15,17,19-nonaene
  参考文献：
  名称：

  Unprecedented Vilsmeier Formylation:  Expedient Syntheses of the Cruciferous Phytoalexins Sinalexin and Brassilexin and Discovery of a New Heteroaromatic Ring System

  摘要：

  A very concise first synthesis of sinalexin was achieved by regioselective formylation of 1-methoxyindoline-2 thione under Vilsmeier conditions followed by unprecedented ammonia workup, Similar formylation of indoline-2-thione yielded brassilexin and a novel pentacyclic heteroaromatic compound resulting from condensation of the Vilsmeier adduct of indoline-2-thione. Both sinalexin and brassilexin displayed strong antifungal activity against several pathogens of crucifers.

  DOI：

  10.1021/ol015691y
• 作为产物：
  描述：

  1,3-二氢-2H-吲哚-2-硫酮 在 盐酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 5H-thiopyrano[2,3-b:6,5-b']diindole
  参考文献：
  名称：

  十字花科植物抗毒素Brassilexin，Sinalexin，Wasalexins和类似物的简明合成：扩大Vilsmeier甲酰化的范围

  摘要：

  通过将Vilsmeier甲酰化应用到二氢吲哚-2-硫酮上，然后进行新的氨水后处理程序，证明了植物抗毒素黄铜素，芥辣素和类似物的有效合成。类似地，描述了使用顺式吲哚-2-酮的甲酰化-氨化非常精确的两锅合成植物抗毒素wasalexins。引人注目的是，这种新颖的氨水后处理允许顺序进行一锅甲酰化氨化反应，从而大大扩大了吲哚啉-2-硫酮和吲哚-2-酮的维尔斯迈尔甲酰化作用的范围。据报道，甲酰化-胺化反应的检查和条件的优化，以及几种黄铜蛋白类似物的合成和抗真菌活性。

  DOI：

  10.1021/jo0479866

文献信息

• A new route to the versatile synthesis of thiopyrano[2,3-b:6,5-b′]diindoles via 2-(alkylthio)-indole-3-carbaldehydes
  作者：Mukund Jha、Michael Edmunds、Kate-lyn Lund、Ashley Ryan

  DOI：10.1016/j.tetlet.2014.08.100

  日期：2014.10

  versatile synthesis of symmetrically and unsymmetrically substituted thiopyrano[2,3-b:6,5-b′]diindoles has been developed by the condensation of 2-(alkylthio)-indole-3-carbaldehydes with indoline-2-thiones in the presence of catalytic amount of ethylenediamine diacetate (EDDA). The EDDA mediated condensation leads to a spontaneous cyclization followed by aromatization to form thiopyrano[2,3-b:6,5-b′]diindoles

  通过2-（烷硫基）-吲哚-3-甲醛与二氢吲哚-2-硫酮的缩合反应，已开发出一种通用的对称和不对称取代的噻喃并[2,3- b：6,5- b ']二吲哚化合物。存在催化量的乙二胺二乙酸酯（EDDA）。EDDA介导的缩合导致自发环化，然后进行芳构化，以定量收率形成噻喃并[2,3- b：6,5- b ']二吲哚。
• Synthesis and biological evaluation of fused thio- and selenopyrans as new indolocarbazole analogues with aryl hydrocarbon receptor affinity
  作者：Emma Wincent、Hamid Shirani、Jan Bergman、Ulf Rannug、Tomasz Janosik

  DOI：10.1016/j.bmc.2008.12.072

  日期：2009.2

  A series of thio- and selenopyrans having two fused indole units, structurally related to indolocarbazoles, have been prepared and evaluated for aryl hydrocarbon receptor (AhR) affinity, leading to the identification of several new significant AhR ligands. In particular, the parent thiopyrano[2,3-b: 6,5-b'] diindole and its derivative having a methyl group in the central ring, as well as the two corresponding selenopyrans, displayed the highest potencies of the compounds tested. (C) 2009 Elsevier Ltd. All rights reserved.
• Concise Syntheses of the Cruciferous Phytoalexins Brassilexin, Sinalexin, Wasalexins, and Analogues:  Expanding the Scope of the Vilsmeier Formylation
  作者：M. Soledade C. Pedras、Mukund Jha

  DOI：10.1021/jo0479866

  日期：2005.3.1

  the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential formylation−amination of indolin-2-ones is described. Remarkably, this novel aqueous ammonia workup allows the sequential one-pot formylation−amination, expanding substantially the scope of the Vilsmeier formylation

  通过将Vilsmeier甲酰化应用到二氢吲哚-2-硫酮上，然后进行新的氨水后处理程序，证明了植物抗毒素黄铜素，芥辣素和类似物的有效合成。类似地，描述了使用顺式吲哚-2-酮的甲酰化-氨化非常精确的两锅合成植物抗毒素wasalexins。引人注目的是，这种新颖的氨水后处理允许顺序进行一锅甲酰化氨化反应，从而大大扩大了吲哚啉-2-硫酮和吲哚-2-酮的维尔斯迈尔甲酰化作用的范围。据报道，甲酰化-胺化反应的检查和条件的优化，以及几种黄铜蛋白类似物的合成和抗真菌活性。
• Unprecedented Vilsmeier Formylation:  Expedient Syntheses of the Cruciferous Phytoalexins Sinalexin and Brassilexin and Discovery of a New Heteroaromatic Ring System
  作者：M. Soledad C. Pedras、Irina L. Zaharia

  DOI：10.1021/ol015691y

  日期：2001.4.1

  A very concise first synthesis of sinalexin was achieved by regioselective formylation of 1-methoxyindoline-2 thione under Vilsmeier conditions followed by unprecedented ammonia workup, Similar formylation of indoline-2-thione yielded brassilexin and a novel pentacyclic heteroaromatic compound resulting from condensation of the Vilsmeier adduct of indoline-2-thione. Both sinalexin and brassilexin displayed strong antifungal activity against several pathogens of crucifers.