N-[2-(1,3-benzothiazol-2-yl)phenyl]benzamide

• 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: N-[2-(1,3-benzothiazol-2-yl)phenyl]benzamide
• 英文别名: N-(2-(benzothiazole-2-yl)phenyl)benzamide；N-[2-(benzothiazol-2-yl)phenyl]benzamide；N-(2-(benzo[d]thiazol-2-yl)phenyl)benzamide
• 化学式: C₂₀H₁₄N₂OS
• 分子量: 330.41
• InChiKey: HVAYLEYCWGZQDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-硝基-苯基)-苯并噻唑 在 tin(II) chloride dihdyrate 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.0h， 生成 N-[2-(1,3-benzothiazol-2-yl)phenyl]benzamide
  参考文献：
  名称：

  Benzothiazole possessing reversible and reusable selective chemosensor for fluoride detection based on inhibition of excited state intramolecular proton transfer

  摘要：

  A series of three benzothiazole derivatives BTBAs based on aryl amide groups have been developed, whose photophysical properties were remarkably changed by the presence of -OCH3 and -NO2 groups at para-position of aryl amides. Among these chemosensors, BTBA-OCH3 showed fluoride selectivity in its absorbance and emission behavior among the various interfering anions, along with conspicuous color change from colorless to yellowish green color. Substantially red shifted absorption as well as fluorescence band of BTBA-OCH3 in DMSO, was observed upon addition of F- ions. Inhibition of Excited State Intramolecular Proton Transfer (ESIPT) in sensor-anion deprotonated complex was suggested to be the signaling mechanism. H-1 NMR titrations of the sensor with F- ions also supported deprotonation process. In particular, the spectral responses of this chemosensor could be tuned from side to side alternatively by adding F- and HSO4- anions in DMSO solvent. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.06.032

文献信息

• Rh(III)-Catalyzed C–H Amidation of Arenes with <i>N</i>-Methoxyamide as an Amidating Reagent
  作者：Guodong Ju、Guobao Li、Guanwen Qian、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1021/acs.orglett.9b02625

  日期：2019.9.20

  The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating

  通过使用N-甲氧基酰胺作为新型氨基源，已经报道了Rh（III）催化的C（sp2）-H键的酰胺化反应。当使用N-甲氧基酰胺衍生物作为酰胺化试剂时，可以达到极好的官能团耐受性。重要的是，可以将几种已知的生物活性化合物（例如阿米那隆，普瑞巴林，加巴喷丁和丙磺舒）转化为有效的酰胺化试剂，以利于开发新的生物活性分子。
• 一种铑催化合成N-[2-(2-芳基苯并噻唑)]-酰 胺的方法
  申请人：江西师范大学

  公开号：CN108250157B

  公开（公告）日：2021-12-21

  本发明公开了一种铑催化合成N‑[2‑(2‑芳基苯并噻唑)]‑酰胺的方法：以二氯(五甲基环戊二烯基)合铑(III)二聚体为催化剂，六氟锑酸银为添加剂，2‑芳基苯并噻唑以及1,4,2‑双恶唑‑5‑酮为反应物，DCE为溶剂，110‑120℃下搅拌24h，反应结束后反应液后处理得到N‑[2‑(2‑芳基苯并噻唑)]‑酰胺。本发明的合成方法具有催化剂用量小、毒性小，原料易制得，官能团普适性较好等特点。
• Intermolecular coupling of 2-iodoanilides with benzoxazoles: synthesis of N-(2-Benzoxazol-2-ylphenyl)benzamides via C–H activation
  作者：Swarnendu Sasmal、Indira Sen、Roger G. Hall、Sitaram Pal

  DOI：10.1016/j.tetlet.2015.01.150

  日期：2015.3

  Using CuI/xantphos/Pd(OAc)(2) catalytic system, the intermolecular C-C cross coupling between benzoxazoles and ortho-haloanilides has been developed in moderate to good yields. The procedure tolerates a series of functional groups on benzoxazole, such as ester, chloro, methyl, and methoxy groups. This divergent approach provides access to various N-(2-Benzoxazol-2-ylphenyl)amides. (C) 2015 Elsevier Ltd. All rights reserved.
• Rh-Catalyzed C–H Amidation of 2-Arylbenzo[<i>d</i>]thiazoles: An Approach to Single Organic Molecule White Light Emitters in the Solid State
  作者：Deming Liu、Qiuping Ding、Yang Fu、Zhibin Song、Yiyuan Peng

  DOI：10.1021/acs.orglett.9b00115

  日期：2019.4.19

  A Rh-catalyzed direct C-H amidation of 2-arylbenzo[d]thiazoles has been developed. The transformation is characterized by its efficiency, external oxidant-free conditions, and the avoidance of a traditional three-step process consisting of nitration, ammoniation, and amidation. Furthermore, several of the prepared molecules exhibit bright white-light emission in the solid state.
• Benzothiazole possessing reversible and reusable selective chemosensor for fluoride detection based on inhibition of excited state intramolecular proton transfer
  作者：Gargi Dhaka、Jasvinder Singh、Navneet Kaur

  DOI：10.1016/j.ica.2016.06.032

  日期：2016.8

  A series of three benzothiazole derivatives BTBAs based on aryl amide groups have been developed, whose photophysical properties were remarkably changed by the presence of -OCH3 and -NO2 groups at para-position of aryl amides. Among these chemosensors, BTBA-OCH3 showed fluoride selectivity in its absorbance and emission behavior among the various interfering anions, along with conspicuous color change from colorless to yellowish green color. Substantially red shifted absorption as well as fluorescence band of BTBA-OCH3 in DMSO, was observed upon addition of F- ions. Inhibition of Excited State Intramolecular Proton Transfer (ESIPT) in sensor-anion deprotonated complex was suggested to be the signaling mechanism. H-1 NMR titrations of the sensor with F- ions also supported deprotonation process. In particular, the spectral responses of this chemosensor could be tuned from side to side alternatively by adding F- and HSO4- anions in DMSO solvent. (C) 2016 Elsevier B.V. All rights reserved.