2-(benzo[d]thiazol-2-yl)-5-phenyl-1,3,4-oxadiazole | 55439-45-7

• 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-(benzo[d]thiazol-2-yl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-(1,3-Benzothiazol-2-yl)-5-phenyl-1,3,4-oxadiazole
• CAS: 55439-45-7
• 化学式: C₁₅H₉N₃OS
• 分子量: 279.322
• InChiKey: OUSCTLPOJOUGLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(benzo[d]thiazol-2-yl)-5-phenyl-1,3,4-oxadiazole 、 diphosphorus pentasulfide 以55%的产率得到
  参考文献：
  名称：

  SAWHNEY S. N; SINGH J.; BANSAL O. P., J. INDIAN CHEM. SOC. , 1974, 51, NO 10, 886-890

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-benzothiazoloyl)-N'-benzylidenehydrazine 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到2-(benzo[d]thiazol-2-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Prakash, Om; Sharma, Vijay; Batra, Hitesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 8, p. 797 - 800

  摘要：

  DOI：

文献信息

• Pd(OAc)2 catalyzed C–H activation of 1,3,4-oxadiazoles and their direct oxidative coupling with benzothiazoles and aryl boronic acids using Cu(OAc)2 as an oxidant
  作者：N. Salvanna、Gandolla Chinna Reddy、Biswanath Das

  DOI：10.1016/j.tet.2012.12.080

  日期：2013.3

  The first direct oxidative coupling of 1,3,4-oxadiazoles with benzothiazoles has been accomplished using Pd(OAc)2 as a catalyst and Cu(OAc)2 as an oxidant. The similar combination of the catalyst and the oxidant has also been applied for direct arylation of 1,3,4-oxadiazoles with aryl boronic acids. Several novel oxadiazole derivatives have been prepared in high yields following both the methods.

  使用Pd（OAc）2作为催化剂和Cu（OAc）2作为氧化剂已经实现了1,3,4-恶二唑与苯并噻唑的首次直接氧化偶联。催化剂和氧化剂的类似组合也已用于将1,3,4-恶二唑与芳基硼酸直接芳基化。两种方法都以高收率制备了几种新的恶二唑衍生物。
• Copper(II)-Catalyzed Dehydrogenative Cross-Coupling between Two Azoles
  作者：Xurong Qin、Boya Feng、Jiaxing Dong、Xiaoyu Li、Ying Xue、Jingbo Lan、Jingsong You

  DOI：10.1021/jo301128y

  日期：2012.9.7

  The copper(II)-catalyzed dehydrogenative coupling between two different azoles for the preparation of unsymmetrical biazoles has been developed. The current catalytic system can effectively control the chemoselectivity for heterocoupling over homocoupling.

  已经开发出铜（II）催化的两种不同唑之间的脱氢偶联，用于制备不对称联唑。当前的催化系统可以有效地控制用于异质偶联比均质偶联的化学选择性。
• Palladium catalyzed direct C–H arylation of 1,3,4-oxadiazole using ligand combination approach
  作者：Sneha Prasad Bakare、Mahendra Patil

  DOI：10.1016/j.tet.2024.133885

  日期：2024.4

  The use of combination of readily available ligands in palladium catalyzed C–H arylation of 1,3,4-oxadiazole with iodoarenes as well as bromoarenes is reported. The combination of phenanthroline monohydrate (Phen.HO) and triphenyl phosphine (PPh) with Pd catalyst exhibited improved catalytical activity compared to a single ligand used separately in the reaction. A wide range of 2,5-diarylated-1,3,4-oxadiazoles

  据报道，在钯催化的 1,3,4-恶二唑与碘芳烃以及溴芳烃的 C-H 芳基化反应中使用易于获得的配体组合。与反应中单独使用的单一配体相比，菲咯啉一水合物 (Phen.HO) 和三苯基膦 (PPh) 与 Pd 催化剂的组合表现出更高的催化活性。使用该方法合成了多种 2,5-二芳基化-1,3,4-恶二唑，其 C-5 位芳基成分有所不同。总体而言，该方法表现出广泛的底物范围和高官能团耐受性。此外，该方法还用于合成咔唑/恶二唑和联苯/恶二唑基杂化化合物，这些化合物以其有趣的光物理性质而闻名。
• Copper(II)-Mediated Dehydrogenative Cross-Coupling of Heteroarenes
  作者：Zhifeng Mao、Zhe Wang、Zhaoqing Xu、Fei Huang、Zhengkun Yu、Rui Wang

  DOI：10.1021/ol301517y

  日期：2012.8.3

  Cu(OAc)(2)-mediated dehydrogenative cross-coupling between two heteroarenes has been realized in the absence of any other additive. A mechanism involving a formal Cu(II) to Cu(0) route by convergent disproportionation of the copper mediator is proposed and has been evidenced by copper mirror formation during the reaction. This synthetic protocol provides a concise and "green" access to unsymmetrical biheteroarenes bearing structural motifs of substantial utility in organic synthesis.
• Sawhney,S.N. et al., Journal of the Indian Chemical Society, 1974, vol. 51, p. 886 - 890
  作者：Sawhney,S.N. et al.

  DOI：——

  日期：——