3-(trifluoromethyl)phenanthridin-6(5H)-one

• 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: 3-(trifluoromethyl)phenanthridin-6(5H)-one
• 英文别名: 3-(trifluoromethyl)-5H-phenanthridin-6-one
• 化学式: C₁₄H₈F₃NO
• 分子量: 263.219
• InChiKey: LBEVXVGYKZGLHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(三氟甲基)-[1,1'-联苯基]-2-胺 在 sodium persulfate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 37.5h， 生成 3-(trifluoromethyl)phenanthridin-6(5H)-one
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Phenanthridinones from Biaryl-2-oxamic Acid under Radical Conditions

  摘要：

  Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products.

  DOI：

  10.1021/ol503459s

文献信息

• A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls
  作者：Zhilong Chen、Xiaodong Wang

  DOI：10.1039/c7ob01237c

  日期：——

  Tricyclic biaryls are important scaffold structures in many natural products and lead compounds in drug discovery. The formation of a biaryl unit is often the key step for the synthesis of tricyclic biaryls. Despite significant progress toward the synthesis of biaryl compounds in recent years, the direct cross-coupling of two different aryl halides is still challenging and robust methods are lacking

  三环联芳基在许多天然产物中是重要的支架结构，在药物发现中是先导化合物。联芳基单元的形成通常是合成三环联芳基的关键步骤。尽管近年来在合成联芳基化合物方面取得了重大进展，但是两种不同的芳基卤化物的直接交叉偶联仍然具有挑战性，并且缺乏可靠的方法。在本文中，我们报道了在钯催化剂和硼酸酯存在下两种不同的芳基卤化物的直接交叉偶联，这为合成三环联芳基提供了一种新的有用的互补方法。
• Woodroofe, Carolyn C.; Zhong, Boyu; Lu, Xingliang, Journal of the Chemical Society. Perkin transactions II, 2000, # 1, p. 55 - 60
  作者：Woodroofe, Carolyn C.、Zhong, Boyu、Lu, Xingliang、Silverman, Richard B.

  DOI：——

  日期：——
• Transition-Metal-Free Synthesis of Phenanthridinones from Biaryl-2-oxamic Acid under Radical Conditions
  作者：Ming Yuan、Li Chen、Junwei Wang、Shenjie Chen、Kongchao Wang、Yongbo Xue、Guangmin Yao、Zengwei Luo、Yonghui Zhang

  DOI：10.1021/ol503459s

  日期：2015.1.16

  Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products.