N-(5-methoxyquinolin-8-yl)-3-phenylpropanamide | 1514926-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(5-methoxyquinolin-8-yl)-3-phenylpropanamide
• CAS: 1514926-94-3
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: ABQLPRHRIDGIAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(5-methoxyquinolin-8-yl)-3-phenylpropanamide 在 2,3,4,5,6-五氟碘苯 、 silver(I) acetate 、 palladium diacetate 作用下， 以73%的产率得到1-(5-methoxyquinolin-8-yl)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β-Lactams

  摘要：

  An efficient method to synthesize the beta-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular arnination of simple and readily available aminoquinoline carboxamides was demonstrated. C6F5I plays a significant role in the formation of the C-N bond of the four-membered ring beta-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived beta-lactams. This method has been applied to the efficient synthesis of the beta-lactamase inhibitor MK-8712.

  DOI：

  10.1021/ol403364k
• 作为产物：
  描述：

  5-甲氧基喹啉-8-胺 、 3-苯丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以92%的产率得到N-(5-methoxyquinolin-8-yl)-3-phenylpropanamide
  参考文献：
  名称：

  Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β-Lactams

  摘要：

  An efficient method to synthesize the beta-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular arnination of simple and readily available aminoquinoline carboxamides was demonstrated. C6F5I plays a significant role in the formation of the C-N bond of the four-membered ring beta-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived beta-lactams. This method has been applied to the efficient synthesis of the beta-lactamase inhibitor MK-8712.

  DOI：

  10.1021/ol403364k

文献信息

• Asymmetric Synthesis of β-Lactam via Palladium-Catalyzed Enantioselective Intramolecular C(sp³)–H Amidation
  作者：Hua-Rong Tong、Wenrui Zheng、Xiaoyan Lv、Gang He、Peng Liu、Gong Chen

  DOI：10.1021/acscatal.9b04768

  日期：2020.1.3

  organic synthesis. Catalytic reactions featuring intramolecular C–H amidation of alkyl carboxamide substrates could provide a straightforward disconnection strategy for β-lactam synthesis. Herein, we report a streamlined method for asymmetric synthesis of β-aryl β-lactams from propanoic acid and aryl iodides via Pd-catalyzed sequential C(sp3)–H functionalization. The lactam-forming reaction provides

  β-内酰胺是药物设计中的重要支架，经常用作有机合成中的反应性中间体。烷基羧酰胺底物分子内CH酰胺化反应的催化反应可为β-内酰胺合成提供简单的断开策略。在这里，我们报告了一种通过Pd催化的连续C（sp 3）-H官能团从丙酸和碘代芳烃不对称合成β-芳基β-内酰胺的简化方法。内酰胺形成反应提供了Pd II催化的对映选择性分子内C（sp 3）-H酰胺化反应的一个例子，反应进行到94％ee。使用2-甲氧基-5-氯苯基碘化物氧化剂对于控制Pd IV竞争性的还原消除途径至关重要中间体以达到所需的化学选择性。机理研究表明，非常规芳基碘化物氧化剂的空间和电子效应都可控制Pd IV中间体的竞争性C–N与C–C还原消除途径。