8-bromoquinoline N-oxide | 90279-39-3

• 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: 8-bromoquinoline N-oxide
• 英文别名: Quinoline, 8-bromo-, 1-oxide；8-bromo-1-oxidoquinolin-1-ium
• CAS: 90279-39-3
• 化学式: C₉H₆BrNO
• 分子量: 224.057
• InChiKey: DCMSRJCCVQNZMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-bromoquinoline N-oxide 在 氯化亚砜 作用下， 反应 12.0h， 以50%的产率得到8-溴-2-氯喹啉
  参考文献：
  名称：

  Rh(III)-Catalyzed C(8)–H Activation of Quinoline N-Oxides: Regioselective C–Br and C–N Bond Formation

  摘要：

  A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis-(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.

  DOI：

  10.1021/acs.joc.9b01538
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溴 、 potassium bromide 作用下， 生成 8-bromoquinoline N-oxide
  参考文献：
  名称：

  Ukai et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 823

  摘要：

  DOI：

文献信息

• TsCl-promoted sulfonylation of quinoline N-oxides with sodium sulfinates in water
  作者：Sha Peng、Yan-Xi Song、Jun-Yi He、Shan-Shan Tang、Jia-Xi Tan、Zhong Cao、Ying-Wu Lin、Wei-Min He

  DOI：10.1016/j.cclet.2019.08.002

  日期：2019.12

  sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal- and oxidant-free conditions has been developed. The mild reaction conditions, high reaction efficiency, operational simplicity, short reaction time and remarkable functional-group compatibility make the developed protocol very attractive for the preparation of 2-sulfonyl N-heteroaromatic compounds.

  摘要建立了一种在环境温度下在无金属和无氧化剂条件下通过杂芳族N-氧化物与亚磺酸钠的磺酰化反应合成各种2-磺酰基喹啉/吡啶的环保方案。温和的反应条件，高的反应效率，操作简便，反应时间短和显着的官能团相容性使所开发的方案对于制备2-磺酰基N-杂芳族化合物非常有吸引力。
• Copper‐Catalyzed <i>ortho</i> ‐Functionalization of Quinoline <i>N</i> ‐Oxides with Vinyl Arenes
  作者：Hui Hu、Xiaoping Hu、Yuanhong Liu

  DOI：10.1002/anie.202007699

  日期：2020.10.19

  An efficient copper‐catalyzed regioselective C−H alkenylation and borylative alkylation of quinoline N‐oxides with vinyl arenes in the presence of pinacol diborane has been developed. The reaction proceeds through the borylcupration of the vinyl arenes followed by nucleophilic attack of the resulting alkyl copper species to the quinoline N‐oxides. Benzoquinone and KOtBu were identified as the necessary

  在频哪醇乙硼烷存在下，开发了一种高效的铜催化的区域选择性CH链烯基化和喹啉N-氧化物与乙烯基芳烃的硼化烷基化反应。该反应通过乙烯基芳烃的硼基杯化进行，然后对所得的烷基铜物质进行亲核攻击，生成喹啉N-氧化物。苯醌和KO t Bu被确定为反应第二步必不可少的添加剂，它们对反应的成功至关重要。获得了多种具有良好官能团耐受性的C2官能化喹啉，可在制药和合成化学中找到用途。
• Synthesis of heteroaromatic trifluoromethyl ethers with trifluoromethyl triflate as the source of the trifluoromethoxy group
  作者：Qing-Wei Zhang、John F. Hartwig

  DOI：10.1039/c8cc05084h

  日期：——

  A series of nitrogen-heterocycles have been transformed to the corresponding trifluoromethyl or higher perfluoroalkyl ethers by reaction of the corresponding N-oxides with trifluoromethyl or higher perfluoroalkyl triflate. Trifluoromethyl triflate, which has generally been used as a precursor to [OCF3]−, is used here as a bifunctional reagent to render the heteroarene more electrophilic and to deliver

  通过使相应的N-氧化物与三氟甲基或更高级的全氟烷基三氟甲磺酸酯反应，将一系列氮杂环转化为相应的三氟甲基或更高级的全氟烷基醚。通常用作[OCF 3 ] -的前体的三氟甲基三氟甲磺酸酯在这里用作双功能试剂，以使杂芳基更具亲电性并传递三氟甲氧基。该试剂易于大规模制备（> 100克），并且无论是纯净形式还是储液形式均稳定。报告了这种方法的应用和局限性。
• Visible-light-induced deoxygenative C2-sulfonylation of quinoline <i>N</i>-oxides with sulfinic acids
  作者：Long-Yong Xie、Tai-Gang Fang、Jia-Xi Tan、Bo Zhang、Zhong Cao、Li-Hua Yang、Wei-Min He

  DOI：10.1039/c9gc01175g

  日期：——

  The first example of visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids in the presence of an organic dye as the catalyst was developed. The reaction conditions are eco-friendly and mild, employing ambient air as the sole oxidant and aqueous acetone solution as the solvent. This approach requires only a very low catalyst loading, allowing gram-scale preparation

  在有机染料作为催化剂的存在下，开发了可见光诱导的喹啉N-氧化物与亚磺酸的C2-磺酰化的第一个例子。该反应条件对环境友好且温和，采用环境空气作为唯一氧化剂，并使用丙酮水溶液作为溶剂。该方法仅需极低的催化剂负载量，即可进行克级制备以及对带有喹啉基团的生物活性化合物进行后期修饰。
• Gold-Catalyzed Regio- and Stereoselective Alkenylation of Quinoline N-Oxides with Allenamides
  作者：Mingduo Lu、Yuanhong Liu

  DOI：10.1021/acs.orglett.4c01796

  日期：2024.7.5

  A gold-catalyzed cycloaddition/ring opening of allenamides with quinoline N-oxides has been developed, which provides C2-alkenylated quinolines with high E selectivity in moderate to high yields. It is noted that quinoline N-oxides with a C8 or C7 substituent are crucial for this catalytic reaction.

  开发了金催化的联烯酰胺与喹啉N-氧化物的环加成/开环反应，以中等到高产率提供具有高E选择性的 C2-烯基化喹啉。值得注意的是，具有C8或C7取代基的喹啉N-氧化物对于该催化反应至关重要。