2-(p-tolylethynyl)benzo[d]thiazole | 362604-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(p-tolylethynyl)benzo[d]thiazole
• 英文别名: 2-[2-(4-Methylphenyl)ethynyl]-1,3-benzothiazole
• CAS: 362604-08-8
• 化学式: C₁₆H₁₁NS
• 分子量: 249.336
• InChiKey: NODDXQLLOGCSCN-UHFFFAOYSA-N

物化性质

• 沸点：
  402.0±38.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(p-tolylethynyl)benzo[d]thiazole 以 乙醚 为溶剂， 生成 (Z)-2-(2-methoxy-2-p-tolypethylene)-3-prop-2-ynyl benzothiazolium triflate
  参考文献：
  名称：

  N-propargyl-2-alkynylbenzothiazolium aza-enediynes: role of the 2-alkynylbenzothiazolium functionality in DNA cleavage

  摘要：

  The 2-alkynylbenzothiazolium salts 3a-d incorporating an N-propargyl moiety have been prepared as aza-enediyne analogues. While these aza-enediynes are shown to be modest DNA cleavage agents, DNA cleavage was also observed with the N-methyl-2-alkynylbenzothiazolium salt 4, which lacks the aza-enediyne moiety. The structural requirements for DNA cleavage, and the correlation of DNA cleavage efficiency with the propensity of these compounds to undergo nucleophilic addition by methanol support a proposed DNA cleavage mechanism involving DNA alkylation. by appropriate 2-alkynyl-substituted benzothiazolium salts. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00606-0
• 作为产物：
  描述：

  苯并噻唑 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 copper(l) iodide 、 四溴化碳 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(p-tolylethynyl)benzo[d]thiazole
  参考文献：
  名称：

  通过 Pd 催化的杂芳基卤化物与末端炔烃的偶联合成内炔烃

  摘要：

  功能化杂环卤化物与末端炔烃的 Sonogashira 型交叉偶联在室温下有效地进行。杂芳基卤化物很容易由相应的杂环化合物制备。催化系统可耐受的底物范围非常广泛；恶唑、噻唑和呋喃首次参与此类反应。该反应为杂环的直接官能化提供了一种有效的方法。

  DOI：

  10.1002/ejoc.201201689

文献信息

• Room-Temperature Direct Alkynylation of Arenes with Copper Acetylides
  作者：Cédric Theunissen、Gwilherm Evano

  DOI：10.1021/ol502030y

  日期：2014.9.5

  C–H bond in azoles and polyhalogenated arenes can be smoothly activated by copper acetylides to give the corresponding alkynylated (hetero)arenes by simple reaction at room temperature in the presence of phenanthroline and lithium tert-butoxide under an oxygen atmosphere. These stable, unreactive, and readily available polymers act as especially efficient and practical reagents for the introduction

  唑和多卤代芳烃中的C–H键可以通过乙炔铜平滑活化，在氧气气氛下，在邻菲咯啉和叔丁醇锂存在下，在室温下通过简单反应，得到相应的炔基化（杂）芳烃。这些稳定的，无反应性的和容易获得的聚合物充当特别有效和实用的试剂，用于在非常温和的条件下将炔基引入众多的芳烃中。
• Copper-assisted palladium catalyzed the cross-coupling reaction of Alknylalane reagents with 2-Thiobenzo[d]thiazoles via C–S bond cleavage
  作者：Hong-Liu Xiao、Xiao-Ying Jia、Jia-Xia Pu、Li-Rong Han、Qing-Han Li

  DOI：10.1016/j.tet.2024.133850

  日期：2024.3

  A highly efficient and simple route for the synthesis of 2-alknyl benzo[]thiazoles has been developed by palladium and copper catalyzed the cross-coupling reaction of 2-thiobenzo[]thiazoles with (hetero)aromatic and aliphatic alkynylaluminum reagents. Various 2-alkynyl benzo[]thiazole derivatives can be obtained in 19–97 % isolated yields using 1 mol% PdCl(dppf)/5 mol% xanthpos as the catalyst and

  通过钯和铜催化2-硫代苯并[]噻唑与(杂)芳香族和脂肪族炔基铝试剂的交叉偶联反应，开发了一种高效、简单的合成2-炔基苯并[]噻唑的路线。使用 1 mol% PdCl(dppf)/5 mol% xantpos 作为催化剂和 CuI（3 当量）作为脱硫剂，可以以 19-97% 的分离收率获得各种 2-炔基苯并[]噻唑衍生物。有机铝试剂或2-硫代苯并[]噻唑类化合物芳香环上的给电子或吸电子基团可以顺利地进行交叉偶联反应。此外，广泛的底物范围和克级高效率的维持使该方案成为合成 2-炔基苯并[]噻唑衍生物的潜在实用方法。根据实验结果，提出了一种可能的催化循环。2009 Elsevier Ltd. 保留所有权利。
• Dehydrogenative and decarboxylative C–H alkynylation of heteroarenes catalyzed by Pd(II)–carbene complex
  作者：Thupakula Parsharamulu、Police Vishnuvardhan Reddy、Pravin R. Likhar、Mannepalli Lakshmi Kantam

  DOI：10.1016/j.tet.2015.02.020

  日期：2015.4

  The direct alkynylation of heteroarenes was accomplished with easily prepared Pd(II) carbene complex (Pd Cat.) by two complementary strategies. Pd Cat. catalysed cross-dehydrogenative coupling of terminal alkynes with heteroarenes was achieved in the first method and decarboxylative coupling of aryl propiolic acids with heteroarenes was investigated in the second method. Both the methodologies tolerate a broad variety of heteroarenes that include benzoxazoles, benzothiazoles, imidazole and benzimidazoles. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Internal Alkynes through the Pd-Catalyzed Coupling of Heteroaryl Halides with Terminal Alkynes
  作者：Linhua Lu、Hong Yan、Peng Sun、Yan Zhu、Hailong Yang、Defu Liu、Guangwei Rong、Jincheng Mao

  DOI：10.1002/ejoc.201201689

  日期：2013.3

  Sonogashira-type cross-couplings of functionalized heterocyclic halides with terminal alkynes were performed efficiently at room temperature. The heteroaryl halides were easily prepared from the corresponding heterocyclic compounds. The catalytic system tolerated a very broad scope of substrates; oxazoles, thiazoles, and furans participate in this type of reaction for the first time. This reaction

  功能化杂环卤化物与末端炔烃的 Sonogashira 型交叉偶联在室温下有效地进行。杂芳基卤化物很容易由相应的杂环化合物制备。催化系统可耐受的底物范围非常广泛；恶唑、噻唑和呋喃首次参与此类反应。该反应为杂环的直接官能化提供了一种有效的方法。
• N-propargyl-2-alkynylbenzothiazolium aza-enediynes: role of the 2-alkynylbenzothiazolium functionality in DNA cleavage
  作者：Dalip Kumar、Wendi M David、Sean M Kerwin

  DOI：10.1016/s0960-894x(01)00606-0

  日期：2001.11

  The 2-alkynylbenzothiazolium salts 3a-d incorporating an N-propargyl moiety have been prepared as aza-enediyne analogues. While these aza-enediynes are shown to be modest DNA cleavage agents, DNA cleavage was also observed with the N-methyl-2-alkynylbenzothiazolium salt 4, which lacks the aza-enediyne moiety. The structural requirements for DNA cleavage, and the correlation of DNA cleavage efficiency with the propensity of these compounds to undergo nucleophilic addition by methanol support a proposed DNA cleavage mechanism involving DNA alkylation. by appropriate 2-alkynyl-substituted benzothiazolium salts. (C) 2001 Elsevier Science Ltd. All rights reserved.