2,8-二苯基二苯并[b,d]噻吩 | 101228-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2,8-二苯基二苯并[b,d]噻吩
• 英文名称: 2,8-diphenyldibenzo[b,d]thiophene
• 英文别名: 2,8-diphenyldibenzothiophene；2,8-Diphenyl-dibenzo-thiophene
• CAS: 101228-48-2
• 化学式: C₂₄H₁₆S
• 分子量: 336.457
• InChiKey: FWMOBNBMZSAAJV-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C
• 沸点：
  559.3±19.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,8-二苯基二苯并[b,d]噻吩 在 lithium 、 1,1,2,2-四苯乙烯 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 以90%的产率得到meta-quaterphenyl
  参考文献：
  名称：

  Active-alkali metal promoted reductive desulfurization of dibenzothiophene and its hindered analogues

  摘要：

  Dibenzothiophene and some related organosulfur compounds are efficiently reductively desulfurized under mild reaction conditions, with Na and/or Li metal in the presence of a catalytic amount of tetraphenylethylene in THF at room temperature. This simple methodology was applied to the synthesis of several substituted biphenyls, thus realizing a connection between the directing properties of the sulfur atom of dibenzothiophene and the efficiency of 1,2-dianions of tetraphenylethane as homogenous electron transfer reagents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.044
• 作为产物：
  描述：

  二苯并噻吩 在 四(三苯基膦)钯 、 溴 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 氯仿 、 水 为溶剂， 生成 2,8-二苯基二苯并[b,d]噻吩
  参考文献：
  名称：

  Active-alkali metal promoted reductive desulfurization of dibenzothiophene and its hindered analogues

  摘要：

  Dibenzothiophene and some related organosulfur compounds are efficiently reductively desulfurized under mild reaction conditions, with Na and/or Li metal in the presence of a catalytic amount of tetraphenylethylene in THF at room temperature. This simple methodology was applied to the synthesis of several substituted biphenyls, thus realizing a connection between the directing properties of the sulfur atom of dibenzothiophene and the efficiency of 1,2-dianions of tetraphenylethane as homogenous electron transfer reagents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.044

文献信息

• Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation
  作者：Atsushi Kaga、Hirokazu Iida、Shun Tsuchiya、Hayate Saito、Koji Nakano、Hideki Yorimitsu

  DOI：10.1002/chem.202005223

  日期：2021.3.8

  A new mode of aromatic metamorphosis has been developed, which allows thiophenes and their benzo‐fused derivatives to be converted to a variety of exotic heteroles. This transformation involves 1) the efficient generation of key 1,4‐dianions by means of desulfurative dilithiation with lithium powder and 2) the subsequent trapping of the dianions with heteroatom electrophiles in a one‐pot manner. Via

  已经开发出一种新的芳香族变态模式，该模式可以将噻吩及其苯并稠合的衍生物转化为各种奇异的杂环。这种转变包括：1）通过用锂粉进行脱硫二锂化反应有效地生成关键的1,4-二价阴离子； 2）随后通过一锅法用杂原子亲电试剂捕获二价阴离子。通过脱硫脱氢作用，噻吩的硫原子也被碳-碳双键或1,2-亚苯基取代，用于构建苯环。
• Transition-Metal-Free Synthesis of Carbazoles and Indoles by an S_NAr-Based “Aromatic Metamorphosis” of Thiaarenes
  作者：M. Bhanuchandra、Kei Murakami、Dhananjayan Vasu、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/anie.201503671

  日期：2015.8.24

  dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The “aromatic metamorphosis” of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron‐deficient thiaarene dioxides exhibit interesting reactivity

  通过母体二苯并噻​​吩的氧化容易制备的二苯并噻吩二氧化物在一次操作中在分子内然后在分子内经历苯胺的亲核芳香取代，然后生成分子内相应的咔唑。二苯并噻吩向咔唑的“芳香变形”不需要任何重金属。该策略也适用于吲哚的合成。由于缺电子的硫杂芳烃二氧化物表现出有趣的反应性，而相应的富电子氮杂芳烃则未观察到，因此，二氧化硫杂ar特定反应与基于S N Ar的芳族变态反应的结合，使得无过渡金属的结构成为可能。难以制备咔唑。
• Palladium-Assisted “Aromatic Metamorphosis” of Dibenzothiophenes into Triphenylenes
  作者：Dhananjayan Vasu、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/anie.201501992

  日期：2015.6.8

  Two new palladium‐catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4‐chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium‐catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate

  芳香族硫化合物的两个新的钯催化反应使二苯并噻吩在四个步骤中转化为苯并菲。一种芳族骨架向另一种芳族骨架的转化包括：1）二苯并噻吩的4-氯丁基化反应形成相应的sulf盐； 2）钯盐与四芳基硼酸钠的钯催化的芳基开环反应； 3）分子内S N 2反应以形成teraryl锍盐，和4）的钯催化的分子内ç  S / C  H至电palladation耦合。以量身定制的方式合成了所需的对称和不对称的三亚苯基，其总收率令人满意。
• Rhodium-Catalyzed Sequential Dehydrogenation/Deoxygenation in One-Pot: Efficient Synthesis of Dibenzothiophene Derivatives from Diaryl Sulfoxides
  作者：Qiufeng Huang、Shurong Fu、Shaojia Ke、Hanbing Xiao、Xiaofeng Zhang、Shen Lin

  DOI：10.1002/ejoc.201501075

  日期：2015.10

  A novel strategy for the synthesis of dibenzothiophene derivatives is established through a one-pot intramolecular cross-dehydrogenative-coupling reaction of diaryl sulfoxides followed by deoxygenation with a Rh/Ag catalytic system. The yields obtained were good to excellent (up to 96 %), therefore making the described protocol an attractive option for building dibenzothiophene compounds.

  通过二芳基亚砜的一锅式分子内交叉脱氢偶联反应，然后用 Rh/Ag 催化体系脱氧，建立了一种合成二苯并噻吩衍生物的新策略。获得的产率从好到极好（高达 96%），因此使所描述的协议成为构建二苯并噻吩化合物的有吸引力的选择。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20160028021A1

  公开（公告）日：2016-01-28

  A composition comprising a first compound and a second compound is described. The composition can be a mixture of a first compound having a structure according to Formula I, and a second compound having a structure according to Formula II, The composition can also be a mixture of a first compound having a structure according to Formula III, and a second compound having a structure according to Formula IV, Devices, such as OLEDs, that include the compositions for Formulas I & II or Formulas III & IV, as well as, methods of making the same are also described.

  描述了一种包含第一化合物和第二化合物的组合物。该组合物可以是根据化学式I结构的第一化合物和根据化学式II结构的第二化合物的混合物。该组合物也可以是根据化学式III结构的第一化合物和根据化学式IV结构的第二化合物的混合物。还描述了包含化学式I和II或化学式III和IV的组合物的设备，如OLEDs，以及制造这些设备的方法。