3,4-dibromo-2,5-dimethylthiophene-S-oxide | 301677-76-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3,4-dibromo-2,5-dimethylthiophene-S-oxide
• 英文别名: 3,4-Dibromo-2,5-dimethylthiophene S-monoxide；3,4-dibromo-2,5-dimethylthiophene-1-monoxide；3,4-Dibromo-2,5-dimethylthiophene 1-oxide
• CAS: 301677-76-9
• 化学式: C₆H₆Br₂OS
• 分子量: 285.987
• InChiKey: ALCQYXZUNIJYFT-UHFFFAOYSA-N

物化性质

• 沸点：
  283.6±40.0 °C(Predicted)
• 密度：
  2.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-2,5-dimethylthiophene-S-oxide 在 tert-butylammonium hexafluorophosphate(V) 、 苯甲酸 作用下， 以 乙腈 为溶剂， 以92%的产率得到2,4-二溴-3,5-二甲基噻吩
  参考文献：
  名称：

  Photochemical and electrochemical behavior of thiophene-S-oxides

  摘要：

  The photochemical and electrochemical behavior of thiophene-S-oxides as a class was studied for the first time. It was shown that in both cases deoxygenation of the S-O functionality takes place. The outcome of the photoirradiation is very dependent on the substituent pattern of the starting material. Thiophene-S-oxides show different reduction behaviors in presence and absence of proton donors. In the absence of proton donors the reduction potential of the compounds is dependent on the substituents of the molecules. In the presence of proton donors, the substituents play a less significant role and a number of thiophene-S-oxides were reduced electrochemically to the corresponding thiophenes in presence of a 10-fold excess of benzoic acid. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200010)13:10<648::aid-poc290>3.0.co;2-t
• 作为产物：
  描述：

  2,4-二溴-3,5-二甲基噻吩 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 生成 3,4-dibromo-2,5-dimethylthiophene-S-oxide
  参考文献：
  名称：

  从噻吩S-氧化物到 7-噻二环[2.2.1]庚-5-烯

  摘要：

  具有 7-硫双环 [2.2.1]hept-5-ene 单元的低聚环已通过噻吩 S-氧化物与烯烃的环加成反应立体选择性制备，随后用 PBr3 对环加合物的磺氧基桥进行脱氧。

  DOI：

  10.3184/030823409x12562932030738

文献信息

• [4 + 2] Cycloaddition of thiophene S-monoxides to activated methylenecyclopropanes
  作者：Thies Thiemann、Daisuke Ohira、Yuanqiang Li、Tsuyoshi Sawada、Shuntaro Mataka、Karsten Rauch、Mathias Noltemeyer、Armin de Meijere

  DOI：10.1039/b003850o

  日期：——

  determined as being endo,syn. The Wittig olefination of cyclopropanone hemiacetal to generate the methylenecyclopropanes and the subsequent cycloaddition can be carried out in a one-pot operation. This procedure is one of many potential one-pot or multi-component reactions involving stabilized phosphoranes. A further example of this type of reaction is shown in the novel desilylation–Wittig olefination

  噻吩小号-oxides 4已经显示出经历[4 + 2]环加成与亚甲基环2与一个或两个电子受体取代基，即甚至在四取代的2-氯-2- cyclopropylideneacetate 2C反应很好。但是，对于四取代的烯烃双（亚环丙基）2f，必须施加高压使其与4反应。在所有反应中仅形成一种非对映异构体。的两个cycloadducts，X射线晶体结构分析图3a和3f中，已经执行，它们的相对配置确定为内切，顺。环丙烷半缩醛的Wittig烯烃化反应生成亚甲基环丙烷，随后的环加成反应可以一锅操作进行。该过程是涉及稳定的膦烷的许多潜在的一锅法或多组分反应之一。这种新型反应的另一个例子是新型的甲硅烷基化-1-乙氧基-1-三甲基甲硅烷基氧基环丙烷5的Wittig烯化反应，一步一步产生环亚丙基乙酸酯，例如2a。
• The mechanism of the heterogeneous catalytic monooxidation of thiophene derivatives at the S position by hydrogen peroxide
  作者：I. T. Nagieva

  DOI：10.1134/s0036024409110119

  日期：2009.1

  A biomimetic catalytic reaction system for hetero-oriented monooxidation of heteroaromatic compounds was developed experimentally. The system consisted of two interacting synchronous reactions of the decomposition of H2O2 and substrate oxidation. The problem related to the preparation, isolation, and identification of thiophene derivative S-monoxides was solved.
• Mass spectrometric study of heterogeneous catalytic monooxidation of the S-position of thiophenes with hydrogen peroxide
  作者：I. T. Nagieva

  DOI：10.1134/s0036024409130330

  日期：2009.1

  A biomimetic catalytic reaction system is developed experimentally for heteromonooxidation of heteroaromatic compounds. The system consists of two interacting simultaneous reactions, decomposition of H2O2 and oxidation of the substrate. This leads to the synthesis, isolation, and identification of the S-monoxide of thiophenes.