6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]pyrrole | 467242-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]pyrrole
• 英文别名: 1-Methyl-1H-4,6,7,8-pentahia-1-aza-azulene；6-methylpentathiepino[6,7-b]pyrrole
• CAS: 467242-28-0
• 化学式: C₅H₅NS₅
• 分子量: 239.431
• InChiKey: VKMSHSBRBPPUAW-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 沸点：
  463.1±37.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]pyrrole 在 三乙烯二胺 、 二氯化二硫 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 6,8-dichloro-7-methyl-7H-(1,2,3,4,5)pentathiepino(6,7-c)pyrrole
  参考文献：
  名称：

  一步合成融合五肽。

  摘要：

  在室温下用S2Cl2和氯仿中的碱处理诸如吡咯和噻吩之类的亲核杂环及其四氢衍生物，可以简单地一锅合成杂环稠合的单和双五硫平，例如2,3、4、5、9，和11。

  DOI：

  10.1039/b203349f
• 作为产物：
  描述：

  1-甲基吡咯烷 在 bis(4-aza-1-azoniabicyclo[2.2.2]oct-1-yl)disulfide dichloride 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以29%的产率得到6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]pyrrole
  参考文献：
  名称：

  Regioselective synthesis of pentathiepines fused with pyrrole, thiophene, or indole rings

  摘要：

  通过相应的杂环化合物或其四氢衍生物与预先制备的硫单氯化物和DABCO混合物反应，获得了与吡咯、噻吩或吲哚环融合的Pentathiepines。

  DOI：

  10.1007/s11172-006-0551-1
• 作为试剂：
  描述：

  sodium benzenesulfonate 在 6-methyl-6H-[1,2,3,4,5]pentathiepino[6,7-b]pyrrole 作用下， 生成 sodium phenylthiosulfonate
  参考文献：
  名称：

  从戊硫平合成1,4-二硫辛。

  摘要：

  稠合的芳香族和杂环1,2,3,4,5- pentathiepins与带有吸电子基团的三苯基膦和炔反应，以高收率得到相应的1,4-二硫辛。不对称炔烃区域选择性地添加以提供与拟议的反应中间体中的电子分布一致的产物。提出了这些反应的机制。

  DOI：

  10.1021/ol0617042

文献信息

• A one-step synthesis of fused pentathiepinsElectronic supplementary information (ESI) available: characterization of compounds 2–5, 9, and 11. See http://www.rsc.org/suppdata/cc/b2/b203349f/
  作者：Lidia S. Konstantinova、Oleg A. Rakitin、Charles W. Rees

  DOI：10.1039/b203349f

  日期：2002.5.17

  Treatment of nucleophilic heterocycles like pyrroles and thiophene, and their tetrahydro derivatives, with S2Cl2 and a base in chloroform at room temperature provides a simple one-pot synthesis of heterocyclic fused mono and bis pentathiepins such as 2, 3, 4, 5, 9, and 11.

  在室温下用S2Cl2和氯仿中的碱处理诸如吡咯和噻吩之类的亲核杂环及其四氢衍生物，可以简单地一锅合成杂环稠合的单和双五硫平，例如2,3、4、5、9，和11。
• Direct synthesis of fused 1,2,3,4,5-pentathiepins
  作者：Stanislav A. Amelichev、Lidia S. Konstantinova、Konstantin A. Lyssenko、Oleg A. Rakitin、Charles W. Rees

  DOI：10.1039/b508186f

  日期：——

  Treatment of nucleophilic heterocycles like pyrroles and thiophenes, and their tetrahydro derivatives, with S2Cl2 and DABCO in chloroform at room temperature provides a simple one-pot synthesis of fused mono and bispentathiepins. N-Methylpyrrole and its 2-chloro and 2,5-dichloro derivatives and N-methylpyrrolidine all give the same dichloropentathiepin 1a. N-Ethyl, isopropyl and tert-butylpyrrolidine behave similarly; the isopropylpyrrolidine also gives the bispentathiepin 6 which undergoes an intriguing rearrangement to the symmetrical monopentathiepin 1c. N-Methyl and ethyl indole give either 2,3-dichloro derivatives 8 or the pentathiepinoindoles 9, depending upon the reaction conditions. Thiophene and tetrahydrothiophene give the pentathiepin 10. X-Ray crystal structures are provided for the pentathiepins 1a and 1d, and possible reaction pathways are suggested for the extensive cascade reactions reported.

  在室温下，将亲核性杂环如吡咯和噻吩及其四氢衍生物与S2Cl2和DABCO在氯仿中反应，可以简单地一步合成融合的单和双五元硫杂环戊烷。N-甲基吡咯及其2-氯和2,5-二氯衍生物以及N-甲基吡咯烷均生成相同的二氯五元硫杂环戊烷1a。N-乙基、异丙基和叔丁基吡咯烷的行为类似；异丙基吡咯烷还生成了双五元硫杂环戊烷6，后者经历了一个有趣的重组变为对称的单五元硫杂环戊烷1c。N-甲基和乙基吲哚根据反应条件分别生成2,3-二氯衍生物8或五元硫杂环戊烷吲哚9。噻吩和四氢噻吩生成五元硫杂环戊烷10。提供了五元硫杂环戊烷1a和1d的X射线晶体结构，并为报道的大量级联反应提出了可能的反应途径。
• Regioselective synthesis of pentathiepino-fused pyrroles and indoles
  作者：Lidia S. Konstantinova、Oleg A. Rakitin、Charles W. Rees、Stanislav A. Amelichev

  DOI：10.1070/mc2004v014n03abeh001912

  日期：2004.1

  Treatment of simple pyrroles, pyrrolidines and indoles with S2Cl2 and Dabco in chloroform at room temperature gives their fused pentathiepino derivatives 4, 6 and 8 in extensive cascade reactions; the reaction profile is changed and the regioselectivity enhanced when the S2Cl2 and Dabco are premixed and equilibrated before the heterocycle is added.
• Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study
  作者：Lidia S. Konstantinova、Stanislav A. Amelichev、Pavel A. Belyakov、Dmitry V. Khakimov、Tatyana S. Pivina、Konstantin A. Lyssenko、Oleg A. Rakitin

  DOI：10.1016/j.tet.2011.10.113

  日期：2012.1

  Pentathiepinopyrroles reacted with methyl propiolate and triphenylphosphine to give regioselectively dithiinopyrroles in agreement with the electron distribution in the proposed reaction intermediate. Thieno[2,3-f][1,2,3,4,5]pentathiepin when treated with methyl propiolate and triphenylphosphine gave a pair of regioisomers where the higher yielding regioisomer contained the same mode of junction as in the case of pentathiepinopyrroles. X-ray crystal structures are provided for the thieno[2,3-b][1,4]dithiine carboxylate isomers. Quantum-chemical calculations B3LYP/6-31G(d) and B3LYP/6-311(++)G(d,p) have been carried out for better understanding of the reaction mechanisms; the index of synchronism of the S-h addition and the index of a relative difference in bond orders in transition states are in good agreement with the formation of the regioisomers by the reaction of unsymmetrical pentathiepins with alkynes containing one electron-withdrawing group. (C) 2011 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of pentathiepines fused with pyrrole, thiophene, or indole rings
  作者：L. S. Konstantinova、S. A. Amelichev、O. A. Rakitin

  DOI：10.1007/s11172-006-0551-1

  日期：2006.11

  Pentathiepines fused with pyrrole, thiophene, or indole rings were obtained by reactions of the corresponding heterocycles or their tetrahydro derivatives with a prepared mixture of sulfur monochloride and DABCO.

  通过相应的杂环化合物或其四氢衍生物与预先制备的硫单氯化物和DABCO混合物反应，获得了与吡咯、噻吩或吲哚环融合的Pentathiepines。