1-(difluoromethyl)quinolin-2(1H)-one | 2341-26-6

• 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: 1-(difluoromethyl)quinolin-2(1H)-one
• 英文别名: 1-(difluoromethyl)quinolin-2-one
• CAS: 2341-26-6
• 化学式: C₁₀H₇F₂NO
• 分子量: 195.168
• InChiKey: ROLKVUHBNUYBSL-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  244.9±40.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(quinolin-2-yl)acetamide 在 potassium hydrogensulfate 、 18-冠醚-6 、 sodium chlorodifluoroacetate 作用下， 以 乙腈 为溶剂， 反应 31.0h， 生成 1-(difluoromethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Facile One-Pot Synthesis of N-Difluoromethyl-2-pyridone Derivatives

  摘要：

  A novel one-pot synthesis of N-difluoromethyl-2-pyridones is described. N-(Pyridin-2-yl) acetamide derivatives were excellent precursors for the preparation of N- difluoromethyl-2-pyridone derivatives. Difluoromethylation of 2-acetaminopyridine derivatives was achieved with sodium chlorodifluoroacetate as a difluorocarbene source in the presence of a catalytic amount of 18-crown-6. Subsequent in situ hydrolysis of resultant 1,2-dihydro-2-acetimino-1-difluoromethylpyridines proceeded under mild acidic conditions to afford the corresponding N-difluoromethyl-2-pyridones in moderate to good yields.

  DOI：

  10.1021/ol061481f

文献信息

• Chemoselective <i>N</i>- and <i>O</i>-Difluoromethylation of 2-Pyridones, Isoquinolinones, and Quinolinones with TMSCF₂Br
  作者：Ziyue Zhu、Vinayak Krishnamurti、Xanath Ispizua-Rodriguez、Colby Barrett、G. K. Surya Prakash

  DOI：10.1021/acs.orglett.1c02305

  日期：2021.8.20

  An operationally simple protocol for direct N- and O-difluoromethylation of 2-pyridones, quinolinones, and isoquinolinones using commercially available TMSCF2Br is disclosed. The chemoselectivity is modulated by simple variations in temperature, solvent, and strength of the base. Diverse, synthetically relevant functional groups are tolerated, including functional groups that have reported reactivity

  公开了使用可商购的 TMSCF 2 Br直接对 2-吡啶酮、喹啉酮和异喹啉酮进行N-和O-二氟甲基化的操作简单的方案。化学选择性通过温度、溶剂和碱强度的简单变化来调节。可以耐受多种合成相关的官能团，包括已报告与 TMSCF 2 Br反应的官能团。包括制备N - 和O - 二氟甲基化合物的克级反应。
• Direct Synthesis of <i>N</i>-Difluoromethyl-2-pyridones from Pyridines
  作者：Sen Zhou、Xiaoya Hou、Kai Yang、Minjie Guo、Wentao Zhao、Xiangyang Tang、Guangwei Wang

  DOI：10.1021/acs.joc.1c00228

  日期：2021.5.7

  A novel method for the synthesis of N-difluoromethyl-2-pyridones was described. This protocol enables the synthesis of N-difluoromethyl-2-pyridones from readily available pyridines using mild reaction conditions that are compatible with a wide range of functional groups. The preliminary mechanistic study revealed that N-difluoromethylpyridinium salts were the key intermediates to complete this conversion

  描述了一种合成N-二氟甲基-2-吡啶酮的新方法。该方案能够使用温和的反应条件，从易得的吡啶中合成N-二氟甲基-2-吡啶酮，该反应条件与多种官能团相容。初步的机理研究表明，N-二氟甲基吡啶鎓盐是完成该转化的关键中间体。