2-(4-甲基苯基)-5-甲氧基苯并噻唑 | 101078-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(4-甲基苯基)-5-甲氧基苯并噻唑
• 英文名称: 2-(4-methylphenyl)-5-methoxybenzothiazole
• 英文别名: 5-methoxy-2-(4-tolyl)-1,3-benzothiazole；5-methoxy-2-(p-tolyl)benzothiazole；5-methoxy-2-(4-tolyl)benzothiazole；5-methoxy-2-(4′-tolyl)benzo[d]thiazole；5-methoxy-2-(p-tolyl)benzo[d]thiazole；5-Methoxy-2-(4-methylphenyl)-1,3-benzothiazole
• CAS: 101078-50-6
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: FCMHKXNZQDSNFF-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  403.8±47.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-甲基苯基)-5-甲氧基苯并噻唑 在 氢溴酸 作用下， 反应 9.0h， 生成 2-(4-甲基苯基)-5-乙酰氧基苯并噻唑
  参考文献：
  名称：

  Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator

  摘要：

  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.

  DOI：

  10.1021/jm00155a037
• 作为产物：
  描述：

  对甲基苯甲酰氯 在 劳森试剂 、 吡啶 、 氢氧化钾 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 2-(4-甲基苯基)-5-甲氧基苯并噻唑
  参考文献：
  名称：

  Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator

  摘要：

  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.

  DOI：

  10.1021/jm00155a037

文献信息

• 2-Arylation/alkylation of benzothiazoles using superparamagneticgraphene oxide-Fe₃ O₄ hybrid material as a heterogeneous catalystwith diisopropyl azodicarboxylate (DIAD) as an oxidant
  作者：Dariush Khalili、Elham Etemadi-Davan、Ali Reza Banazadeh

  DOI：10.1002/aoc.3971

  日期：2018.1

  nanocomposites as a heterogeneous catalyst for arylation/alkylation of benzothiazoles with aldehydes and benzylic alcohols in the presence of diisopropyl azodicarboxylate (DIAD) as an oxidant which exclusively produced 2‐aryl (alkyl)‐1H–benzothizoles in moderate to excellent yields. The absence of precious metals and toxic solvent, easy product isolation, and recyclability of the GO‐Fe3O4 with no loss of

  在本报告中，我们介绍了氧化石墨烯-氧化铁（GO-Fe 3 O 4）纳米复合物，作为在偶氮二羧酸二异丙酯（DIAD）作为氧化剂存在下苯并噻唑与醛和苄醇的芳基化/烷基化反应的非均相催化剂2-芳基（烷基）-1 H-苯并噻唑的产率中等至优异。该方法的显着优点是不存在贵金属和有毒溶剂，易于产品分离以及GO‐Fe 3 O 4的可回收性而不损失活性。
• Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines
  作者：Masahiro Teramoto、Takumi Mizuno、Mitsutaka Imoto、Motonori Takeda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1055/a-1430-5100

  日期：2021.7

  sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical

  这项研究旨在开发基于氧化还原环化的绿色和可持续的先进合成方法。元素硫显示出在不存在过渡金属催化剂和溶剂的情况下，通过氧化还原环化作用，可以由2,2'-二硝基二苯基二硫化物和苄基胺促进2-取代的苯并噻唑的高效合成。以良好至优异的产率获得2-取代的苯并噻唑。该合成方法是高度原子经济的，不需要任何外部氧化剂和/或还原剂。
• The cross-coupling reaction of organoalane reagents with 2-methylthiobenzo[<i>d</i>]thiazoles<i>via</i>C–S bond cleavage catalyzed by nickel
  作者：Xin Jiang、Hongliu Xiao、Xiaoying Jia、Jiaxia Pu、Lirong Han、Qinghan Li

  DOI：10.1039/d3nj02026f

  日期：——

  2-methylthiobenzo[d]thiazoles with aryl and alkenylaluminum reagents. Various 2-(hetero)aryl and 2-alkenyl substituted benzo[d]thiazoles derivatives can be obtained with 31–94% isolated yields using 4 mol% NiCl2(dppf)/4 mol% 2,2′-bipyridine as the catalyst under mild reaction conditions. The coupling reaction can be carried out smoothly whether the electron donor group or electron withdrawing group is on the aromatic

  通过镍催化 2-甲硫基苯并[ d ]噻唑与芳基和烯基铝试剂的交叉偶联，开发了一种高效且简单的合成 2-取代苯并[ d ]噻唑的路线。使用 4 mol% NiCl 2 (dppf)/4 mol% 2,2'-联吡啶作为催化剂，可以得到各种 2-(杂)芳基和 2-烯基取代的苯并[ d ]噻唑衍生物，分离产率为 31-94%在温和的反应条件下。无论给电子基团或吸电子基团在有机铝试剂的芳香环上还是2-甲硫基苯并[ d]上，偶联反应都能顺利进行。]噻唑衍生物。此外，广泛的底物范围和典型的克级高效维持使该方案成为合成 2-取代苯并[d ]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。
• Synthesis of 2-Aryl Benzothiazoles via K2S2O8-Mediated Oxidative Condensation of Benzothiazoles with Benzylamines
  作者：Ze Tan、Ji-Cheng Shi、Zhiyong Yang、Anwei Wang、Xiang Chen、Qingwen Gui、Jidan Liu、Hua Wang

  DOI：10.1055/s-0033-1339193

  日期：——

  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.
• A simple approach to benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine under solvent-free and catalyst-free conditions
  作者：Yao Tong、Qiang Pan、Zengqiang Jiang、Dazhuang Miao、Xuesong Shi、Shiqing Han

  DOI：10.1016/j.tetlet.2014.08.037

  日期：2014.10

  A novel solvent-free and catalyst-free synthesis of benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine has been developed. The reaction tolerated a wide range of functionalities, and various benzothiazoles were synthesized in moderate to good yields in the absence of external oxidant or reductant. (C) 2014 Elsevier Ltd. All rights reserved.