4-vinyldibenzo[b,d]thiophene | 18625-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4-vinyldibenzo[b,d]thiophene
• 英文别名: 4-vinyldibenzothiophene；4-Ethenyldibenzothiophene
• CAS: 18625-82-6
• 化学式: C₁₄H₁₀S
• 分子量: 210.299
• InChiKey: KMSUBZDINAOIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  4-vinyldibenzo[b,d]thiophene 在 偶氮二异丁腈 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-[2-(propylthio)ethyl]dibenzothiophene S-oxide
  参考文献：
  名称：

  Photochemistry of Substituted Dibenzothiophene Oxides: The Effect of Trapping Groups¹

  摘要：

  Photolyses of dibenzothiophene sulfoxides (DBTOs) with intramolecular trapping functionalities attached in the 4-position show higher quantum yields of deoxygenation. Deoxygenation quantum yields are also less solvent dependent for the substituted DBTOs. Product analysis shows a detectable amount of intramolecular O-trapped products and suggests that solvent effects observed in previous studies of DBTO derive at least mainly from the reactivity between the oxidizing species that is released, presumably O(P-3), and the solvent, rather than from other macroscopic solvent parameters.

  DOI：

  10.1021/jo047995e
• 作为产物：
  描述：

  4-碘二苯并噻吩 、 三丁基乙烯基锡 在 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 反应 24.0h， 以55%的产率得到4-vinyldibenzo[b,d]thiophene
  参考文献：
  名称：

  Photochemistry of Substituted Dibenzothiophene Oxides: The Effect of Trapping Groups¹

  摘要：

  Photolyses of dibenzothiophene sulfoxides (DBTOs) with intramolecular trapping functionalities attached in the 4-position show higher quantum yields of deoxygenation. Deoxygenation quantum yields are also less solvent dependent for the substituted DBTOs. Product analysis shows a detectable amount of intramolecular O-trapped products and suggests that solvent effects observed in previous studies of DBTO derive at least mainly from the reactivity between the oxidizing species that is released, presumably O(P-3), and the solvent, rather than from other macroscopic solvent parameters.

  DOI：

  10.1021/jo047995e

文献信息

• Synthesis of Styrenes by Palladium(II)-Catalyzed Vinylation of Arylboronic Acids and Aryltrifluoroborates by Using Vinyl Acetate
  作者：Jonas Lindh、Jonas Sävmarker、Peter Nilsson、Per J. R. Sjöberg、Mats Larhed

  DOI：10.1002/chem.200802744

  日期：2009.4.27

  One Heck of a reaction: Treatment of arylboronic acids or aryltrifluoroborates with vinyl acetate by using a palladium(II) catalyst gives the corresponding styrenes (see scheme). No palladium reoxidant is needed and the vinylation is performed under non‐inert conditions

  反应的一个难题：通过使用钯（II）催化剂，用乙酸乙烯酯处理芳基硼酸或芳基三氟硼酸酯，得到相应的苯乙烯（参见方案）。无需钯再氧化剂，乙烯基化可在非惰性条件下进行
• Porphyrin compositions
  申请人：Litz Erik Kyle

  公开号：US20060152149A1

  公开（公告）日：2006-07-13

  Novel metal porphyrin compositions useful as organic phosphors are provided. The novel compositions are prepared from commercially available porphyrin-containing starting materials. In one instance a novel palladium-containing porphyrin composition having a number average molecular weight of greater than 12,000 grams per mole was prepared from 5,10,15,20-tetrakis(3′,5′-di(hydroxy)phenyl)-21H-23H-porphyrin by reaction first with palladium(II) acetylacetonate, followed by reaction with 2-bromo-2-methylpropionyl bromide, and subsequent group transfer reaction of the alpha-bromo ester groups with 9,9-dioctyl-2-vinylfluorene in the presence of CuBr as a radical initiator. The product polymer exhibited a number average molecular weight of 12,884 grams per mole, a weight average molecular weight of 14,338 grams per mole, and a robust red phosphorescent emission. Porphyrin containing copoylmers comprising structural units derived from 9,9-dioctyl-2-vinylfluorene and 9-anthracenylmethyl methacrylate were prepared in a similar fashion.

  提供用作有机荧光体的新型金属卟啉组合物。这些新型组合物是从商业可获得的含卟啉起始原料制备的。在一个实例中，通过首先与醋酸钯(II)反应，然后与2-溴-2-甲基丙酰溴反应，并在CuBr存在下将α-溴酯基团与9,9-二辛基-2-乙烯基芴进行基团转移反应，制备了一个平均分子量大于12,000克/摩尔的新型含钯卟啉组合物，起始原料为5,10,15,20-四(3′,5′-二(羟基)苯基)-21H-23H-卟啉。该产物聚合物的平均分子量为12,884克/摩尔，重均分子量为14,338克/摩尔，具有稳健的红色磷光发射。类似地制备了含卟啉的共聚物，其结构单元源自9,9-二辛基-2-乙烯基芴和9-蒽甲基丙烯酸甲酯。
• Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes
  作者：Keming Yang、Tian Feng、Youai Qiu

  DOI：10.1002/anie.202312803

  日期：2023.11.6

  Despite widespread use of the deuterium isotope effect, selective deuterium labeling of chemical molecules remains a major challenge. Herein, a facile and general electrochemically driven, organic mediator enabled deuteration of styrenes with deuterium oxide (D₂O) as the economical deuterium source was reported. Importantly, this transformation could be suitable for various electron rich styrenes mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition‐metal catalysts, affording the desired products in good yields with excellent D‐incorporation (D‐inc, up to >99 %). Mechanistic investigations by means of isotope labeling experiments and cyclic voltammetry tests provided sufficient support for this transformation. Notably, this method proved to be a powerful tool for late‐stage deuteration of biorelevant compounds.

  摘要尽管氘同位素效应得到了广泛应用，但化学分子的选择性氘标记仍是一项重大挑战。本文报告了一种以氧化氘（D2O）为经济氘源，通过电化学驱动的有机介质实现苯乙烯氘化的简便、通用方法。重要的是，在三苯基膦（TPP）的介导下，这种转化适用于各种富电子苯乙烯。该反应在温和的条件下进行，无需过渡金属催化剂，能以良好的产率和出色的氘结合率（D-inc，高达 99%）获得所需的产物。通过同位素标记实验和循环伏安测试进行的机理研究为这种转化提供了充分的支持。值得注意的是，这种方法被证明是生物相关化合物后期脱氘的有力工具。
• VERWENDUNG ORGANISCHER MOLEKÜLE IN OPTOELEKTRONISCHEN BAUELEMENTEN
  申请人：cynora GmbH

  公开号：EP3248230B1

  公开（公告）日：2020-05-06
• US7663301B2
  申请人：——

  公开号：US7663301B2

  公开（公告）日：2010-02-16