N-(prop-2-yn-1-yl)benzo[b]thiophene-2-carboxamide | 1090390-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-(prop-2-yn-1-yl)benzo[b]thiophene-2-carboxamide
• 英文别名: T6137576；N-prop-2-ynyl-1-benzothiophene-2-carboxamide
• CAS: 1090390-15-0
• 化学式: C₁₂H₉NOS
• mdl: MFCD10652691
• 分子量: 215.276
• InChiKey: OYDBXBSPBDNFAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(prop-2-yn-1-yl)benzo[b]thiophene-2-carboxamide 在 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-(benzo[b]thiophen-2-yl)-5-methyloxazole
  参考文献：
  名称：

  Facile, Selective, and Regiocontrolled Synthesis of Oxazolines and Oxazoles Mediated by ZnI₂ and FeCl₃

  摘要：

  An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various functionalities was well tolerated to give 2-oxazolines and 2-oxazoles in good to excellent yields under mild reaction conditions.

  DOI：

  10.1021/ol301980g
• 作为产物：
  描述：

  苯并噻吩-2-羰酰氯 、 炔丙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(prop-2-yn-1-yl)benzo[b]thiophene-2-carboxamide
  参考文献：
  名称：

  Facile, Selective, and Regiocontrolled Synthesis of Oxazolines and Oxazoles Mediated by ZnI₂ and FeCl₃

  摘要：

  An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various functionalities was well tolerated to give 2-oxazolines and 2-oxazoles in good to excellent yields under mild reaction conditions.

  DOI：

  10.1021/ol301980g

文献信息

• Bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl–ene reaction for construction of 5-oxazoylmethyl α-silyl alcohol
  作者：Xinpeng Sang、Yuhao Mo、Shiya Li、Xiaohua Liu、Weidi Cao、Xiaoming Feng

  DOI：10.1039/d3sc01048a

  日期：——

  A bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl–ene reaction was developed. The reaction proceeded well with a broad range of N-propargylamides and acylsilanes, affording the target chiral 5-oxazoylmethyl α-silyl alcohols in up to 95% yield and 99% ee under mild conditions. Importantly, this facile protocol was available for the late-stage modification of several

  开发了一种双金属串联催化的对映选择性环异构化/羰基-烯反应。该反应与多种N-炔丙基酰胺和酰基硅烷一起顺利进行，在温和条件下以高达 95% 的产率和 99% ee 得到目标手性 5-恶唑酰基甲基 α-硅醇。重要的是，这种简便的方案可用于几种生物活性分子的后期修饰。基于机理研究和控制实验，提出了可能的催化循环和过渡态来阐明反应过程和对映诱导。
• Catalytic (4+2) Annulation via Regio‐ and Enantioselective Interception of in‐situ Generated Alkylgold Intermediate
  作者：Ming Bao、Yi Zhou、Haoxuan Yuan、Guizhi Dong、Chao Li、Xiongda Xie、Kewei Chen、Kemiao Hong、Zhi‐Xiang Yu、Xinfang Xu

  DOI：10.1002/anie.202401557

  日期：2024.7.29

  An enantioselective (4+2) annulation of N-propargylamides and α,β-unsaturated imines/ketones has been accomplished under gold-complex and chiral quinine-derived squaramide synergetic catalysis, providing chiral tetrahydropyridines/dihydropyrans with high efficiency and selectivity. This method complements the (4+2) annulation of allene reagents via a formal cycloaddition on internal π-bond, which is

  在金配合物和手性奎宁衍生的方酰胺协同催化下，完成了N-炔丙基酰胺和α,β-不饱和亚胺/酮的对映选择性(4+2)环化，提供了高效、选择性的手性四氢吡啶/二氢吡喃。该方法通过内部 π-键上的正式环加成补充了丙二烯试剂的 (4+2) 环化，这具有挑战性并且仍然难以捉摸。