N-(2-(pyridin-2-yl)phenyl)-4-(trifluoromethyl)benzamide | 1581756-84-4

• 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-(pyridin-2-yl)phenyl)-4-(trifluoromethyl)benzamide
• 英文别名: N-(2-pyridin-2-ylphenyl)-4-(trifluoromethyl)benzamide
• CAS: 1581756-84-4
• 化学式: C₁₉H₁₃F₃N₂O
• 分子量: 342.32
• InChiKey: JNRMCFJWQCKNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-三氟甲基苯甲酰氯 在 silver hexafluoroantimonate 、 sodium azide 、 (p-cymene)ruthenium(II) chloride 、 邻硝基苯甲酸 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 18.0h， 生成 N-(2-(pyridin-2-yl)phenyl)-4-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Orthogonal Reactivity of Acyl Azides in C–H Activation: Dichotomy between C–C and C–N Amidations Based on Catalyst Systems

  摘要：

  The dual reactivity of acyl azides was utilized successfully in C-H activation by the choice of catalyst systems: while selective C-C amidation was achieved under thermal Rh catalysis, a Ru catalyst was found to mediate direct C-N amidation also highly selectively. Investigations of the mechanistic dichotomy between two catalytic systems are also presented.

  DOI：

  10.1021/ol500602b

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。
• 10.1039/d4gc01747a
  作者：Saito, Yuki、Konno, Taro、Kobayashi, Shū

  DOI：10.1039/d4gc01747a

  日期：——

  We report a green, continuous-flow C–H amidation methodology using heterogeneous Cp*Rh(III) catalysts. These catalysts enable halide- and salt-free reactions with excellent activity and durability across diverse substrates, demonstrated by a 200-hour, multi-gram scale reaction exceeding 290 TON (turnover number).

  我们报告了一种使用非均相 Cp*Rh(III) 催化剂的绿色连续流 C-H 酰胺化方法。这些催化剂可实现无卤化物和无盐反应，在不同基材上具有优异的活性和耐久性，200 小时、超过 290 吨（周转数）的多克规模反应证明了这一点。
• Orthogonal Reactivity of Acyl Azides in C–H Activation: Dichotomy between C–C and C–N Amidations Based on Catalyst Systems
  作者：Kwangmin Shin、Jaeyune Ryu、Sukbok Chang

  DOI：10.1021/ol500602b

  日期：2014.4.4

  The dual reactivity of acyl azides was utilized successfully in C-H activation by the choice of catalyst systems: while selective C-C amidation was achieved under thermal Rh catalysis, a Ru catalyst was found to mediate direct C-N amidation also highly selectively. Investigations of the mechanistic dichotomy between two catalytic systems are also presented.