2-([1,1'-biphenyl]-4-yl)benzo[d]thiazole | 67362-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-([1,1'-biphenyl]-4-yl)benzo[d]thiazole
• 英文别名: 2-(1,1'-biphenyl-4-yl)benzothiazole；2-(biphenyl-4-yl)benzothiazole；2-([1,1′-biphenyl]-4-yl)benzo[d]thiazole；2-Biphenyl-4-YL-benzo[D]thiazole；2-(4-phenylphenyl)-1,3-benzothiazole
• CAS: 67362-98-5
• 化学式: C₁₉H₁₃NS
• 分子量: 287.385
• InChiKey: MBERSLSESCKEED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-([1,1'-biphenyl]-4-yl)benzo[d]thiazole 在 palladium diacetate 、 copper(ll) bromide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以88%的产率得到2-(3,5-dibromo-1,1′-biphenyl-4-yl)benzo[d]thiazole
  参考文献：
  名称：

  不含过氧化物的Pd（II）催化的芳烃邻位芳基化和邻位卤化

  摘要：

  在末端氧化剂Cu（OAc）2 ·H 2 O存在下，通过交叉脱氢偶联（CDC）开发了Pd（II）催化的无氧芳烃直接芳烃芳烃化。原位产生的苯基乙二醛，这是从2-乙酸基苯乙酮于氧化剂的Cu（OAc）的存在下获得的2 ·H 2 O.然而，改变氧化剂的CuX 2（X =氯，溴）独家提供二邻卤化的2-芳基苯并噻唑。在卤化过程中，CuX 2兼具卤素源和助氧化剂的双重作用。

  DOI：

  10.1021/acs.joc.6b01170
• 作为产物：
  描述：

  4-溴甲基联苯 在 dipotassium peroxodisulfate 、 potassium tert-butylate 作用下， 以 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 2-([1,1'-biphenyl]-4-yl)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis of 2-Aryl Benzothiazoles via K2S2O8-Mediated Oxidative Condensation of Benzothiazoles with Benzylamines

  摘要：

  A novel way to synthesize 2-arylbenzothiazoles is described. Reactions of benzothiazoles with diverse benzylamines in the presence of K2S2O8 and KOt-Bu in DMSO-H2O afforded the desired 2-arylbenzothiazoles in good yields. It is notable that no transition-metal catalyst is needed in this reaction. Compared with other known methods, this method of synthesizing 2-arylbenzothiazoles can be advantageous in cases where substituted benzothiazoles and benzylamines are readily available.

  DOI：

  10.1055/s-0033-1339193

文献信息

• Selective Construction of 2-Substituted Benzothiazoles from <i>o</i>-Iodoaniline Derivatives S₈ and <i>N</i>-Tosylhydrazones
  作者：Yubing Huang、Peiqi Zhou、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.7b03118

  日期：2018.2.16

  Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom

  已经实现了通过铜促进的[3 +1 + 1]型环化反应，由邻碘苯胺衍生物S 8和N-甲苯磺酰zone选择性构建2-取代的苯并噻唑。在该方案中，可以通过改变反应体系来调节N-甲苯磺酰hydr上的碳原子以构建苯并噻唑。此外，该转化实现了多个碳-杂原子键的构建。
• Mild and Highly Efficient Method for the Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles
  作者：Kiumars Bahrami、M. Mehdi Khodaei、Fardin Naali

  DOI：10.1021/jo8010232

  日期：2008.9.1

  A new, convenient method for the syntheses of 2-substituted benzimidazole and benzothizole is described. Short reaction times, large-scale synthesis, easy and quick isolation of the products, excellent chemoselectivity, and excellent yields are the main advantages of this procedure.

  描述了一种新的，方便的合成2-取代的苯并咪唑和苯并噻唑的方法。该方法的主要优点是反应时间短，大规模合成，产物的简便快速分离，优异的化学选择性和优异的收率。
• Fine tuning of emission color of iridium(iii) complexes from yellow to red via substituent effect on 2-phenylbenzothiazole ligands: synthesis, photophysical, electrochemical and DFT study
  作者：Ming Li、Hui Zeng、Yanyan Meng、Huiqin Sun、Song Liu、Zhiyun Lu、Yan Huang、Xuemei Pu

  DOI：10.1039/c1dt10305a

  日期：——

  Four novel iridium(III) complexes bearing biphenyl (7a–7c) or fluorenyl (7d) modified benzothiazole cyclometallate ligands are synthesized. In comparison with the yellow parent complex, bis(2-phenylbenzothiozolato-N,C2′) iridium(III) (acetylacetonate) [(pbt)2Ir(acac)] (λPLmax = 557 nm, φPL = 0.26), 7a–7d show 20–43 nm bathochromic shifted orange or red phosphorescence in solution, with maximum photoluminescence (PL) quantum yield of 0.62, and PL lifetime of 1.8–2.0 μs. Meanwhile, the resulting complexes also exhibit intense orange or red phosphorescence of λPLmax = 588–611 nm in solid films. The complex 7c with two tert-butyl substituents possesses the highest phosphorescent efficiency both in dilute solution and thin solid films, therefore may be a prospective candidate for both doping and host emitting electrophosphorescent material. Furthermore, despite the observation of severe oxygen quenching for 7a–7d in solution, 7a and 7c even show efficient emission intensity quenching by oxygen in their solid state due to the existence of void channels in crystals; consequently, they are promising molecular oxygen sensor reagents. Electrochemical measurement and DFT calculation results suggest that all these chelates own declined LUMOs of 0.1 eV relative to that of (pbt)2Ir(acac) owing to the contribution of the phenyl substituents; whereas only 7d shows a more destabilized HOMO (∼0.1 eV) compared with the parent chelate.

  合成了四种新型铱(III)配合物,分别带有改性的联苯(7a-7c)或芴基(7d)苯并噻唑环金属配体。与黄色母体配合物 bis(2-苯基苯并噻唑-N,C2')铱(III)(乙酰丙酮)[(pbt)2Ir(acac)](λPLmax=557 nm, φPL=0.26)相比,7a-7d在溶液中表现出橙色或红色磷光,最大发射波长红移20-43 nm,最大光致发光(PL)量子产率为0.62,PL寿命为1.8-2.0μs。同时,所得配合物在固态薄膜中也显示出强烈的橙色或红色磷光,最大发射波长为588-611 nm。具有两个叔丁基取代基的配合物7c在稀溶液和薄固态薄膜中都具有最高的磷光效率,因此可能是掺杂和主体发光电磷光材料的有前景的候选材料。此外,尽管在溶液中观察到7a-7d的严重氧猝灭,但7a和7c甚至在固态下由于晶体中存在空隙通道而表现出有效的氧猝灭发射强度;因此,它们是有前景的分子氧传感器试剂。电化学测量和DFT计算结果表明,由于苯基取代基的贡献,所有这些螯合物相对于(pbt)2Ir(acac)的LUMOs下降了0.1 eV;而只有7d的HOMO(约0.1 eV)比母体螯合物更不稳定。
• Elemental sulfur mediated cyclization via redox strategy: Synthesis of benzothiazoles from o -chloronitrobenzenes and benzyl chlorides
  作者：Xin Wang、Dazhuang Miao、Xiaotong Li、Renhe Hu、Zhao Yang、Ren Gu、Shiqing Han

  DOI：10.1016/j.tet.2017.07.013

  日期：2017.8

  A novel metal-free synthesis of 2-substituted benzothiazoles from easily available o-chloronitrobenzenes and benzyl chlorides using elemental sulfur as traceless oxidizing agent has been developed. The protocol provides a simple, efficient, and atom-economic way to access to benzothiazoles in moderate to excellent yields. And the approach exhibited good functional group tolerance.

  已经开发了一种新的无金属的合成方法，该方法使用元素硫作为无痕氧化剂，由易于获得的邻氯硝基苯和苄基氯合成2-取代的苯并噻唑。该协议提供了一种简单，有效且原子经济的方法来以中等至优异的产率获得苯并噻唑。并且该方法表现出良好的官能团耐受性。
• Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines
  作者：Xiaolong Tuo、Shanping Chen、Pingyu Jiang、Penghui Ni、Xiaodong Wang、Guo-Jun Deng

  DOI：10.1039/c9ra10964a

  日期：——

  has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields

  已经开发了一种碘催化的好氧脱氢芳构化，可以直接有效地获得各种苯并唑和苯并嗪。目前的无过渡金属协议能够以分子氧为绿色氧化剂的四氢苯并四氢喹啉以及其他一些 N-杂环进行脱氢芳构化。因此，在简单的反应条件下以中等至良好的产率产生了广泛的杂芳族化合物。