6H-pentathiepino[6,7-b]indole | 157984-19-5

• 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: 6H-pentathiepino[6,7-b]indole
• 英文别名: pentathiepino<6,7-b>indole；pentathiepino[6,7-b]indole；6H-1,2,3,4,5-Pentathiepino[6,7-b]indole
• CAS: 157984-19-5
• 化学式: C₈H₅NS₅
• 分子量: 275.464
• InChiKey: SBHXWSIEGQHCNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  581.2±42.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二氢-2H-吲哚-2-硫酮 在 sodium hydride 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 以42%的产率得到6H-pentathiepino[6,7-b]indole
  参考文献：
  名称：

  Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00660-3

文献信息

• 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。
• Transformation of isatin with P4S10 to pentathiepino[6,7-b]indole in one step
  作者：Jan Bergman、Claes St»lhandske

  DOI：10.1016/s0040-4039(00)77084-5

  日期：1994.7

  Pentathiepino[6,7-b]indole (6) can be isolated from reactions of P4S10 with isatin in pyridine. The structure of 6 has been determined with X-ray crystallography.

  可以从P 4 S 10与吡啶中的Isatin分离出Pentathiepino [6,7-b]吲哚（6）。6的结构已经通过X射线晶体学确定。
• 多取代[1,2,3,4,5]五硫代[6,7-b]吲哚及衍生物的合成方法
  申请人：衡阳师范学院

  公开号：CN116813639A

  公开（公告）日：2023-09-29

  本发明涉及一种多取代[1,2,3,4,5]五硫代[6,7‑b]吲哚及衍生物的合成方法。本发明首次采用在碘化合物的催化下，有机碱活化单质硫，亚砜类化合物作助氧化剂，在空气氛围中，将吲哚类化合物和单质硫转化为多取代[1,2,3,4,5]五硫代[6,7‑b]吲哚及衍生物的技术方案。该技术方案有如下优点：(1)所需试剂性质稳定，无需预处理、廉价易得；(2)一锅法合成，步骤经济性优势明显，省时省力；(3)无需使用过渡金属催化，从根源上杜绝了金属残留问题；(4)使用廉价的碘化合物催化，减少环境污染，节约反应成本；(5)整个反应体系简单，选择性优异，反应设备少，实验操作简便；(6)特别适合用来制备生物活性分子和药物分子。
• Bergman Jan, Stalhandske Claes, Tetrahedron Lett, 35 (1994) N 29, S 5279-5282
  作者：Bergman Jan, Stalhandske Claes

  DOI：——

  日期：——
• 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.