methyl thieno[2,3-b][1,4]dithiine-2-carboxylate | 1000272-77-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl thieno[2,3-b][1,4]dithiine-2-carboxylate
• 英文别名: Methyl thieno[2,3-b][1,4]dithiine-2-carboxylate
• CAS: 1000272-77-4
• 化学式: C₈H₆O₂S₃
• 分子量: 230.332
• InChiKey: YSAAPBGNSQZSSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙炔酸甲酯 、 thieno[2,3-f][1,2,3,4,5]pentathiepin 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以13%的产率得到methyl thieno[2,3-b][1,4]dithiine-2-carboxylate
  参考文献：
  名称：

  Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.10.113

文献信息

• 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.