噻蒽-2-硼酸 | 108847-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 中文名称: 噻蒽-2-硼酸
• 英文名称: 2-thianthrene boronic acid
• 英文别名: Thianthren-2-ylboronic acid
• CAS: 108847-21-8
• 化学式: C₁₂H₉BO₂S₂
• 分子量: 260.145
• InChiKey: GCSOJZMPHLRBMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  226 °C
• 沸点：
  476.4±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  17
• 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：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  噻蒽-2-硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium phosphate dibasic dodecahydrate 、 potassium nitrososulfonate 、 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 38.42h， 生成 5-(2-thianthrenyl)-2-hydroxy-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

  摘要：

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.028

文献信息

• A Highly Efficient Dimeric Manganese‐Catalyzed Selective Hydroarylation of Internal Alkynes
  作者：Yubo Pang、Gengtu Liu、Congcong Huang、Xiang‐Ai Yuan、Weipeng Li、Jin Xie

  DOI：10.1002/anie.202004950

  日期：2020.7.27

  inherent double controlled strategy of sterically hindered propargyl alcohols without the installing of external directing groups. Its synthetic robustness and practicality have been illustrated by the concise synthesis of bervastatin, a hypolipidemic drug, and late‐stage modification of complex alkynes with precise regioselectivity.

  在水存在下，在没有配体参与的空气气氛下，我们已经开发了一种通用且可预测的锰催化内部炔烃加氢芳基化反应。与其他广泛使用的过渡金属催化剂（包括钯，铑，镍或铜）相比，该反应具有独特的催化特性。简单的操作，高效和出色的官能团兼容性使该协议可用于90多种结构不同的内部炔烃，克服了炔烃的电子和空间效应的影响。其独特的区域选择性和化学选择性来自于锰基催化剂对固有的双重控制策略（受阻炔丙基醇）的固有反应性，而无需安装外部引导基团。
• Effect of substituents on the electron transport properties of bay substituted perylene diimide derivatives
  作者：Sivamurugan Vajiravelu、Lygaitis Ramunas、Gražulevičius Juozas Vidas、Gaidelis Valentas、Jankauskas Vygintas、Suresh Valiyaveettil

  DOI：10.1039/b901847f

  日期：——

  Electron donating substituents such as 3,4,5-trimethoxy phenyl (PDI1), thiophene (PDI2), 6-methoxy naphthyl (PDI3), 5-hexyl dithiophene (PDI4) and thioanthrenyl (PDI5) moieties incorporated at the bay region of N,N′-dodecylperylene diimide (PDI) derivatives have been synthesized and characterised. The absorption maxima of PDI1–5 showed a bathochromic shift with considerable peak broadening and merging of vibronic fine structure as compared to that of PDI. The photoinduced intramolecular charge transfer (ICT) from electron donating substituents to the perylene-acceptor has been observed from fluorescence self-quenching. The molecules are stable up to 400 °C and amorphous in nature. The cyclic voltammetry results revealed that the oxidation potential can be tuned by the electron donating capacity of the substituents and the dithiophene-attached perylene derivative (PDI4) showed a very low band gap of 1.57 eV. The electron transporting properties have been studied using xerographic time-of-flight method and the highest electron mobility reached up to 4.4 × 10−4 cm2V−1 s−1 at 6.4 × 105 V cm−1 for 1,7-di(3,4,5-trimethoxyphenyl)perylene diimide (PDI1) under ambient conditions.

  已合成并表征了在N,N′-十二烷基苝二亚胺（PDI）衍生物的湾区引入的电子供体取代基，如3,4,5-三甲氧基苯（PDI1）、噻吩（PDI2）、6-甲氧基萘基（PDI3）、5-己基二噻吩（PDI4）和硫蒽基（PDI5）。与PDI相比，PDI1–5的吸收最大值表现出明显的红移，且峰宽度显著增加，振动精细结构合并。通过荧光自淬灭观察到电子供体取代基向苝受体的光诱导分子内电荷转移（ICT）。这些分子在高达400°C的温度下稳定，并且具有无定型特性。循环伏安法结果表明，氧化电位可以通过取代基的电子供给能力进行调节，连接了二噻吩的苝衍生物（PDI4）显示出非常低的带隙为1.57 eV。使用静电放电时间飞行法研究了电子传输特性，1,7-二（3,4,5-三甲氧基苯基）苝二亚胺（PDI1）在常温条件下的最高电子迁移率达到4.4 × 10−4 cm²V−1 s−1，在电场强度为6.4 × 10⁵ V cm−1时。
• 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
  申请人：Solus Advanced Materials co., Ltd. 솔루스첨단소재 주식회사(120190660630) Corp. No ▼ 214911-0058927BRN ▼668-81-01406

  公开号：KR20180008124A

  公开（公告）日：2018-01-24

  본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층에 사용됨에 따라 유기 전계 발광 소자의 발광 효율, 구동 전압, 수명 등을 향상시킬 수 있다.

  本发明涉及一种新化合物及其在有机电致发光器件中的应用，根据本发明的化合物可用于有机电致发光器件的有机层，进而可改善有机电致发光器件的发光效率、驱动电压、寿命等。
• Synthesis of 1- and 2-substituted thianthrenes
  作者：James M. Lovell、John A. Joule

  DOI：10.1039/p19960002391

  日期：——

  Lithiation of thianthrene at C-1 allows the synthesis of various 1-substituted thianthrenes for example thianthren-1-ylboronic acid and 1-tributylstannylthianthrene, which undergo palladium-catalysed couplings with aryl halides. 2-Bromothianthrene provides an entry to 2-substituted thianthrenes via lithium–halogen exchange then reaction of 2-lithiothianthrene with electrophiles including formation of the 2-boronic acid and 2-tributylstannylthianthrene which were coupled to aryl halides.

  噻蒽 C-1 的锂化反应可以合成各种 1-取代的噻蒽，例如噻蒽-1-基硼酸和 1-三丁基锡噻蒽，它们与芳基卤化物发生钯催化偶联反应。通过锂-卤素交换，2-溴噻蒽进入 2-取代噻蒽，然后 2-硫代噻蒽与亲电物反应，包括形成 2-硼酸和 2-三丁基锡噻蒽，并与芳基卤化物偶联。
• Synthesis of N-alkylated amino acids using fluorous-tagged hydroxylamines
  作者：Simon D. Nielsen、Garrick P. Smith、Mikael Begtrup、Jesper L. Kristensen

  DOI：10.1016/j.tet.2011.05.039

  日期：2011.7

  a new fluorous-tagged ammonia-equivalent for the synthesis of N-alkylated amino acids is described. The required building blocks were readily accessed in high yield and purity using F-SPE purification technique. Coupling of the fluorous-tagged hydroxylamines with a selection of boronic acids and glyoxalic acid gave the desired N-alkylated amino acids. Subsequent removal of the fluorous tag via catalytic

  描述了用于合成N-烷基化氨基酸的等价的带有氟标签的氨的发展。使用F-SPE纯化技术可以轻松获得所需的构建基块，且产率高且纯度高。含氟标签的羟胺与选择的硼酸和乙二酸的偶合得到所需的N-烷基化的氨基酸。随后研究了使用多种不同的催化剂和溶剂通过催化氢化除去氟标签的方法。一种更可靠的去标记程序涉及将氨基酸转化为相应的甲酯，然后进行Mo（CH 3 CN）3（CO）3介导的N–O键裂解。