6-甲氧基-2-(对甲苯基)苯并[D]噻唑 | 101078-51-7

• 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: 6-甲氧基-2-(对甲苯基)苯并[D]噻唑
• 英文名称: 6-methoxy-2-(p-tolyl)benzo[d]thiazole
• 英文别名: 6-methoxy-2-(4-methylphenyl)-1,3-benzothiazole
• CAS: 101078-51-7
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: HYPBHVPYFUNVJM-UHFFFAOYSA-N

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

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应保持干燥和密封保存。

反应信息

• 作为反应物：
  描述：

  6-甲氧基-2-(对甲苯基)苯并[D]噻唑 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氢溴酸 作用下， 以 四氯化碳 为溶剂， 反应 21.25h， 生成 [2-[4-(Diethoxyphosphorylmethyl)phenyl]-1,3-benzothiazol-6-yl] acetate
  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 6-甲氧基-2-(对甲苯基)苯并[D]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

• Metal-Free Synthesis of 2-Arylbenzothiazoles from Aldehydes, Amines, and Thiocyanate
  作者：Amrita Dey、Alakananda Hajra

  DOI：10.1021/acs.orglett.9b00245

  日期：2019.3.15

  A highly efficient method for the synthesis of 2-arylbenzothiazoles has been developed using readily available aromatic amines, benzaldehydes, and NH4SCN as a sulfur source. A library of 2-arylbenzothiazoles with wide functional group compatibility has been synthesized in good yields through iodine-mediated oxidative annulation.

  已经开发了一种高效的合成2-芳基苯并噻唑的方法，该方法使用容易获得的芳族胺，苯甲醛和NH 4 SCN作为硫源。通过碘介导的氧化环化反应，以高收率合成了具有广泛官能团相容性的2-芳基苯并噻唑文库。
• Efficient 2-Aryl Benzothiazole Formation from Aryl Ketones and 2-Aminobenzenethiols under Metal-Free Conditions
  作者：Yunfeng Liao、Hongrui Qi、Shanping Chen、Pengcheng Jiang、Wang Zhou、Guo-Jun Deng

  DOI：10.1021/ol302902e

  日期：2012.12.7

  2-Aryl benzothiazole formation from aryl ketones and 2-aminobenzenethiols under metal- and I2-free conditions was described. Various 2-aryl benzothiazoles were selectively obtained in good yields using molecular oxygen as oxidant. DMSO played an important role in this transformation. Functional groups such as methyl, methoxy, fluoro, chloro, bromo and nitro groups were tolerated under the optimized reaction

  描述了在无金属和无I 2的条件下由芳基酮和2-氨基苯硫醇形成的2-芳基苯并噻唑。使用分子氧作为氧化剂，可以高收率选择性地获得各种2-芳基苯并噻唑。DMSO在此转型中发挥了重要作用。在优化的反应条件下，可以容忍甲基，甲氧基，氟，氯，溴和硝基等官能团。
• Copper-catalyzed solvent-free redox condensation of benzothiazoles with aldehydes or benzylic alcohols
  作者：Mingliang Zhang、Wen-Ting Lu、Wenqing Ruan、Hui-Jun Zhang、Ting-Bin Wen

  DOI：10.1016/j.tetlet.2014.01.120

  日期：2014.3

  2-aryl- and 2-alkyl-substituted benzothiazoles via a copper-catalyzed redox condensation process between benzothiazoles and aldehydes or benzylic alcohols has been developed. The reaction proceeded under mild reaction conditions using environmentally benign tert-butyl hydroperoxide (TBHP) as the oxidant. A reaction mechanism involving the ring-opening of benzothiazoles initiated by the attack of acyl

  已经开发了通过苯并噻唑与醛或苯甲醇之间的铜催化的氧化还原缩合工艺来构建2-芳基-和2-烷基取代的苯并噻唑的有效且实用的方法。反应在温和的反应条件下进行，使用环境友好的叔丁基氢过氧化物（TBHP）作为氧化剂。提出了一种基于苯甲酰二硫化物中间体的分离反应机理，该反应机理涉及通过酰基自由基侵袭噻唑环和分子内缩合引发苯并噻唑的开环。
• Synthesis of 2-Aryl Benzothiazoles via K₂S₂O₈-mediated Oxidative Condensation of Benzothiazoles with Aryl Aldehydes
  作者：Zhiyong Yang、Xiang Chen、Sizhuo Wang、Jidan Liu、Kai Xie、Anwei Wang、Ze Tan

  DOI：10.1021/jo300740j

  日期：2012.8.17

  Nontransition metal-catalyzed synthesis of 2-aryl benzothiazoles was achieved through K2S2O8-mediated oxidative condensation of benzothiazoles with aryl aldehydes. The same transformation can also be effected when the aryl aldehydes were replaced with phenylglyoxylic acids.

  通过K 2 S 2 O 8介导的苯并噻唑与芳基醛的氧化缩合反应，可以实现2-芳基苯并噻唑的非过渡金属催化合成。当芳基醛被苯基乙醛酸代替时，也可以实现相同的转化。
• 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。