bis(1H-indol-2-yl)sulfide | 1134149-39-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis(1H-indol-2-yl)sulfide
• 英文别名: di(1H-indol-2-yl)sulfane；di(1H-indol-2-yl)sulfide；Bisindolyl sulfide；2-(1H-indol-2-ylsulfanyl)-1H-indole
• CAS: 1134149-39-5
• 化学式: C₁₆H₁₂N₂S
• 分子量: 264.351
• InChiKey: XOSJIPCQRSPJJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bis(1H-indol-2-yl)sulfide 在 Oxone 、 sodium azide 、 ammonium cerium (IV) nitrate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 bis(3-((1H-tetrazol-5-yl)thio)-1H-indol-2-yl)sulfide
  参考文献：
  名称：

  对于吲哚和吡咯采用加入CeCl的5-四唑硫基衍生物的合成的简便生态友好的系统3 ·7H 2 ○在PEG-400 †

  摘要：

  据报道，在聚乙二醇400（PEG-400）中使用CeCl 3 ·7H 2 O作为有效和环保的促进剂体系，可方便地合成由吲哚和吡咯衍生的5-亚磺酰基四唑。合成需要使NaN 3与3-硫代氰基吲哚（包括3,3'-二硫代氰基-1 H，1 H '，2,2'-双吲哚）和2-硫代氰基吡咯进行[3 + 2]环加成反应。硫氰酸盐可通过不同取代的起始吲哚，1 H，1 H '，2,2'-双吲哚和N-芳基吡咯与NH 4的异丁酮介导的硫氰酸氰化反应方便地获得SCN。还研究了转换的范围和局限性。

  DOI：

  10.1039/c4ra05625f
• 作为产物：
  描述：

  2-碘-1H-吲哚 在 caesium carbonate 、 硫脲 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以75%的产率得到bis(1H-indol-2-yl)sulfide
  参考文献：
  名称：

  氧化石墨烯催化的S-芳构化负载的氧化铜纳米粒子：芳烃硫化物的高效无配位合成

  摘要：

  AbstractCopper oxide nanoparticles that are supported on graphene oxide as a catalytic system have been utilized for ligand‐free and solvent‐free CS cross‐coupling reactions with weak bases such as triethylamine. Symmetrical/unsymmetrical aryl sulfides have been synthesized by the coupling of different aryl halides with aromatic as well as aliphatic sulfides. Surprisingly, aryl chlorides also well reacted with different types of sulfides in the presence of dimethyl sulfoxide and cesium carbonate. Besides, this catalytic system is suitable for the synthesis of phenothiazines via cascade CS and CN cross‐coupling of ortho‐dihalides and ortho‐aminobenzothiazoles. In addition, this alternative approach is extremely useful for the synthesis of a variety of symmetrical diaryl sulfides by using thiourea as a sulfur source that is devoid of the foul smell of thiols. Indeed, the calculated E‐factor value of our present protocol is 2.52. Furthermore, this protocol is particularly attractive as an environmentally benign and practical method for the synthesis of different aryl sulfides. Moreover, the heterogeneous catalytic system described in this process represents not only a greener approach but retains its significant activity for up to six catalytic cycles.magnified image

  DOI：

  10.1002/adsc.201300416

文献信息

• Preparation of phalloidin and its derivatives
  申请人：Liu Baosheng

  公开号：US20120214968A1

  公开（公告）日：2012-08-23

  The present invention relates to novel phalloidin derivatives and their fluorescent dye conjugates. These new compounds may be used in studies of actin dynamics in living systems. The present invention also relates to methods for preparing such compounds. The synthesis routes combine solid-phase and solution phase peptide synthesis, and has great advantage for efficient preparation of a diverse library of the phalloidin derivatives, especially for the synthesis of phalloidin.

  本发明涉及新型鬼笔环酯衍生物及其荧光染料偶联物。这些新化合物可用于研究活体系统中的肌动蛋白动力学。本发明还涉及制备这类化合物的方法。合成路线结合了固相和溶液相肽合成，对于高效制备多样化的鬼笔环酯衍生物文库具有巨大优势，尤其适用于鬼笔环酯的合成。
• 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.
• JPS63216863A
  申请人：——

  公开号：JPS63216863A

  公开（公告）日：1988-09-09
• US8569452B2
  申请人：——

  公开号：US8569452B2

  公开（公告）日：2013-10-29
• CN115772187
  申请人：——

  公开号：——

  公开（公告）日：——