5,10-dihydro-5,10-dimethyl[1,2,3,4]-tetrathiocino[5,6-b:8,7-b']diindole | 13637-40-6

• 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: 5,10-dihydro-5,10-dimethyl[1,2,3,4]-tetrathiocino[5,6-b:8,7-b']diindole
• 英文别名: 5,10-dimethyl-5,10-dihydro[1,2,3,4]tetrathiocino[5,6-b:8,7-b']diindole；5,10-dimethyl-5H,10H-[1,2,3,4]tetrathiocino[5,6-b:8,7-b']diindole；5,10-dimethyl-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b;8,7-b']diindole；5,10-Dimethyl-5,10-dihydro-diindolo<2,3-e;3',2'-g><1,2,3,4>tetrathiocin；N,N'-Dimethyl-3,3'-diindolyl-2,2'-tetrasulfid；9,16-Dimethyl-11,12,13,14-tetrathia-9,16-diazapentacyclo[13.7.0.02,10.03,8.017,22]docosa-1(15),2(10),3,5,7,17,19,21-octaene
• CAS: 13637-40-6
• 化学式: C₁₈H₁₄N₂S₄
• 分子量: 386.587
• InChiKey: OXCXHKJJCPAZGT-UHFFFAOYSA-N

物化性质

• 熔点：
  256-259 °C
• 沸点：
  696.6±53.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,10-dihydro-5,10-dimethyl[1,2,3,4]-tetrathiocino[5,6-b:8,7-b']diindole 在 镍 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以61%的产率得到1,1'-dimethyl-3,3'-biindole
  参考文献：
  名称：

  Schroth, Werner; Spitzner, Roland; Felicetti, Michael, European Journal of Organic Chemistry, 2000, # 17, p. 3093 - 3102

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1'-dimethyl-3,3'-biindole 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以19%的产率得到5,10-dihydro-5,10-dimethyl[1,2,3,4]-tetrathiocino[5,6-b:8,7-b']diindole
  参考文献：
  名称：

  Thionation of bisindole derivatives with P4S10 or elemental sulfur

  摘要：

  使用元素硫或P4S10在吡啶中对几种双吲哚衍生物的硫化反应进行了研究，导致形成几种新颖的结构。靛蓝或异靛的反应与P4S10生成了结构上新的盐10，该盐可以转化为乙基衍生物11。低产率分离出第一例硫化靛蓝衍生物单硫靛蓝（6），该化合物是通过异靛的硫化反应得到的。将3,3′-双吲哚与硫在热DMF中反应生成了先前已知的四硫化物1，利用X射线晶体学对其进行了研究，从而确认了1在晶态下是手性的。通过X射线晶体学还确定了另外一个硫化产物——噻吲哚衍生物34的结构。

  DOI：

  10.1039/b109840c

文献信息

• Thioxo-analoga isoindigoider verbindungen?
  作者：Werner Schroth、Michael Felicetti、Ekkehard Hintzsche、Roland Spitzner、Maren Pink

  DOI：10.1016/s0040-4039(00)73026-7

  日期：1994.3

  Thioxo-isoindigoide compounds E are accessible only in special cases, depending on the resonance situation in the heterocyclic unit, whereas the thioxo-indigoide species A are at all unknown. Thus the oxidation of the corresponding leuko-isoindigoide precursors affords either 3 as a representative of E by predominance of thioamide conjugation, or the unusual 12-membered cyclic bis-disulfides 4 and 10, respectively, according to type H by predominance of hetarene stabilization.
• The Action of Sulfur on Indole
  作者：Wayne Carpenter、M. S. Grant、H. R. Snyder

  DOI：10.1021/ja01496a022

  日期：1960.6
• Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones
  作者：Gordon W Rewcastle、Tomasz Janosik、Jan Bergman

  DOI：10.1016/s0040-4020(01)00660-3

  日期：2001.8

  The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b ' ]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• CN116969967
  申请人：——

  公开号：——

  公开（公告）日：——
• Thionation of bisindole derivatives with P4S10 or elemental sulfur
  作者：Tomasz Janosik、Jan Bergman、Birgitta Stensland、Claes Stålhandske

  DOI：10.1039/b109840c

  日期：2002.1.23

  Thionation reactions of several bisindole derivatives using elemental sulfur or P4S10 in pyridine have been studied, leading to formation of several novel structures. The reaction of indigo or isatin with P4S10 gave the structurally new salt 10, which could be transformed into the ethyl derivative 11. The first example of a thionated indigo derivative, monothioindigo (6), was isolated in low yield from the thionation of isatin. Treatment of 3,3′-biindolyl with sulfur in hot DMF produced the previously known tetrasulfide 1, which was studied by X-ray crystallography, thus also establishing that 1 is chiral in the crystalline state. The structure of an additional thionation product, the thienoindole derivative 34 was also solved using X-ray crystallography.

  使用元素硫或P4S10在吡啶中对几种双吲哚衍生物的硫化反应进行了研究，导致形成几种新颖的结构。靛蓝或异靛的反应与P4S10生成了结构上新的盐10，该盐可以转化为乙基衍生物11。低产率分离出第一例硫化靛蓝衍生物单硫靛蓝（6），该化合物是通过异靛的硫化反应得到的。将3,3′-双吲哚与硫在热DMF中反应生成了先前已知的四硫化物1，利用X射线晶体学对其进行了研究，从而确认了1在晶态下是手性的。通过X射线晶体学还确定了另外一个硫化产物——噻吲哚衍生物34的结构。