2-(4-methylphenyl)-6-nitrobenzothiazole | 53544-69-7

• 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-(4-methylphenyl)-6-nitrobenzothiazole
• 英文别名: 6-nitro-2-(p-tolyl)benzo[d]thiazole；6-nitro-2-p-tolylbenzo[d]thiazole；6-nitro-2-p-tolylbenzothiazole；6-nitro-2-p-tolyl-benzothiazole；6-Nitro-2-p-tolyl-benzothiazol；2-(4'-Methylphenyl)-6-nitrobenzothiazol；2-(4-Methylphenyl)-6-nitro-1,3-benzothiazole
• CAS: 53544-69-7
• 化学式: C₁₄H₁₀N₂O₂S
• 分子量: 270.312
• InChiKey: CKLICVRYOYUORL-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202.5 °C(Solv: benzene (71-43-2))
• 沸点：
  446.3±47.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)-6-nitrobenzothiazole 、 N-溴代丁二酰亚胺(NBS) 、 硝酸 生成 2-[4-(bromomethyl)phenyl]-6-nitro-1,3-benzothiazole
  参考文献：
  名称：

  YOSHINO, KOHICHIRO;KOHNO, TOSHIHIKO;UNO, TOSHIO;TOMINORI, MORITA;TSUKAMOT+, J. MED. CHEM., 1986, 29, N 5, 820-825

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酰氯 在 双(乙腈)氯化钯(II) 、 1,10-菲罗啉 、 四丁基溴化铵 、 水 、 copper diacetate 、 sodium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 5.08h， 生成 2-(4-methylphenyl)-6-nitrobenzothiazole
  参考文献：
  名称：

  钯与芳基磺酰基酰肼催化的唑类脱硫芳基化反应†

  摘要：

  已经实现了钯与芳基磺酰基酰肼的钯催化的脱硫和脱氮芳基化反应。各种各样的唑和芳基磺酰肼已被用于高产率地生产芳基化的唑。

  DOI：

  10.1039/c2ob26270c

文献信息

• Palladium-catalyzed desulfitative C–H arylation of azoles with sodium sulfinates
  作者：Ru Chen、Saiwen Liu、Xinhua Liu、Luo Yang、Guo-Jun Deng

  DOI：10.1039/c1ob06387a

  日期：——

  A palladium-catalyzed desulfitative C–H arylation of azoles with sodium sulfinates using Cu(OAc)2·H2O as oxidant has been discovered. The reaction proceeded well for a range of different substrates under oxidative conditions. A series of aryl-substituted azoles have been synthesized in moderate to good yields.

  发现了一种使用Cu(OAc)2·H2O作为氧化剂的钯催化下磺酸钠与唑类化合物的脱磺酸C-H偶联反应。该反应在氧化条件下对多种不同底物进行得很顺利，一系列含有芳基取代的唑类化合物被合成为中等到优良的产率。
• Direct C–H arylation of benzothiazoles by magnetically separable nano copper ferrite, a recyclable catalyst
  作者：G. Satish、K. Harsha Vardhan Reddy、B.S.P. Anil、K. Ramesh、R. Uday Kumar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2015.07.002

  日期：2015.8

  A simple and highly practical method for the direct C–H arylation of benzothiazoles has been developed by using nano copper ferrite as a recyclable catalyst. The CuFe2O4 nano could be recovered and reused without significant loss of catalytic activity.

  通过使用纳米铁氧体铜作为可循环利用的催化剂，已经开发出一种简单且高度实用的直接进行苯并噻唑的CH芳基化的方法。可以回收CuFe 2 O 4纳米并重新使用，而不会显着降低催化活性。
• A highly efficient palladium-catalyzed desulfitative arylation of azoles with sodium arylsulfinates
  作者：Min Wang、Dengke Li、Wei Zhou、Lei Wang

  DOI：10.1016/j.tet.2011.12.072

  日期：2012.2

  A highly efficient palladium-catalyzed direct desulfitative arylation of azoles at C2-position has been developed using sodium arylsulfinates as aryl sources. Azoles including benzoxazoles, benzothiazoles, oxazoles, thiazoles, and 1,3,4-oxadiazoles reacted with sodium arylsulfinates smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated

  使用芳基次磺酸钠作为芳基来源，已经开发出了一种高效的钯催化的C2位的吡咯直接脱硫芳基化反应。包括苯并恶唑，苯并噻唑，恶唑，噻唑和1,3,4-恶二唑的唑与芳基亚磺酸钠顺利反应生成相应的产物，收率良好至优异，并且在反应中可以采用各种取代方式。
• Meyer, Chemical news and journal of industrial science, 1922, vol. 124, p. 381,391
  作者：Meyer

  DOI：——

  日期：——
• Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator
  作者：Kohichiro Yoshino、Toshihiko Kohno、Toshio Uno、Tominori Morita、Goro Tsukamoto

  DOI：10.1021/jm00155a037

  日期：1986.5

  A series of 4-(benzothiazol-2-yl)benzylphosphonic acid dialkyl ester derivatives were synthesized and evaluated for coronary vasodilatory activity by Langendorff's method in the isolated guinea pig heart. Many of the phosphonic acid dialkyl esters exhibited vasodilatory activity and calcium antagonism comparable with those of diltiazem hydrochloride, whereas phosphonic acid 1b and its nonphosphonated precursor 7a were inactive. These results indicate the necessity of the diethoxyphosphinyl moiety for vasodilatory activity. Substitution of the benzothiazole ring with a variety of substituents did not significantly enhance the activity of the unsubstituted compound. Compound 10b (KB-944) was chosen for detailed pharmacological evaluation.