3-(4-fluorophenyl)isoquinoline N-oxide | 1426258-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4-fluorophenyl)isoquinoline N-oxide
• 英文别名: 3-(4-Fluorophenyl)-2-oxidoisoquinolin-2-ium
• CAS: 1426258-77-6
• 化学式: C₁₅H₁₀FNO
• 分子量: 239.249
• InChiKey: IOUFTYCUPGWUCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)isoquinoline N-oxide 在 silver trifluoromethanesulfonate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到3-(4-fluorophenyl)isoquinoline
  参考文献：
  名称：

  Efficient Synthesis of Isoquinoline Derivatives via AgOTf/Cu(OTf)₂-Cocatalyzed Cyclization of 2-Alkynyl Benzaldoxime

  摘要：

  An efficient, AgOTf and Cu(OTf)(2) multicatalytic intramolecular cycloisomerization of 2-alkynylbenzaldoxime is reported. Isoquinoline N-oxides have been found to be deoxygenated to the corresponding quinolines in good yields in dimethylformamide/dichloroethane (v/v 5:1) as solvent at 120 degrees C.

  DOI：

  10.1080/00397911.2012.666314
• 作为产物：
  描述：

  (NE)-N-[[2-[2-(4-fluorophenyl)ethynyl]phenyl]methylidene]hydroxylamine 在 copper(l) iodide 、 水 作用下， 以80 %的产率得到3-(4-fluorophenyl)isoquinoline N-oxide
  参考文献：
  名称：

  通过水中铜催化的分子内环化轻松合成异喹啉和异喹啉 N-氧化物。

  摘要：

  开发了一种通过 Cu(i) 催化的 (E)-2-炔基芳基肟衍生物在水中的分子内环化轻松获得异喹啉和异喹啉 N-氧化物的高效方法。该协议是在简单温和的条件下进行的，没有有机溶剂、添加剂或配体。通过打开/关闭肟的羟基保护基团，可以触发选择性 NO/OH 裂解，分别以中等到高产率提供一系列异喹啉和异喹啉 N-氧化物，具有良好的官能团耐受性和高原子经济性。此外，通过分五步全合成莫萨维林进一步证明了该方法的实用性。

  DOI：

  10.1039/d2ra06097c

文献信息

• Generation of 1-aroxyisoquinolines via a silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol in the presence of p -toluenesulfonyl chloride
  作者：Qing Xiao、Danqing Zheng、Qiuping Ding、Jie Wu

  DOI：10.1016/j.tet.2013.04.076

  日期：2013.6

  A silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol promoted by p-toluenesulfonyl chloride leads to 1-aroxyisoquinolines in good yields. The presence of p-toluenesulfonyl chloride as an activator is essential for the successful transformation.

  银的2-炔基苯甲肟与由对甲苯磺酰氯促进的苯酚的银催化反应以良好的收率产生1-芳氧基异喹啉。存在p甲苯磺酰氯作为活化剂是成功转化是必需的。
• AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds
  作者：Qiuping Ding、Dan Wang、Puying Luo、Meiling Liu、Shouzhi Pu、Liyun Zhou

  DOI：10.3762/bjoc.9.231

  日期：——

  AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with various alpha,beta-unsaturated carbonyl compounds under mild conditions are described, which provides a facile and efficient pathway for the synthesis of 1-alkylated isoquinoline derivatives. The method tolerates a wide range of substrates and allows for the preparation of the products of interest in moderate to excellent yields.

  描述了在温和条件下 AgOTf 催化 2-炔基苯甲醛肟与各种 α、β-不饱和羰基化合物的一锅反应，这为合成 1-烷基化异喹啉衍生物提供了一种简便有效的途径。该方法适用于广泛的底物，并允许以中等至极好的产率制备感兴趣的产品。
• One-pot two-step synthesis of 1-position arylated 1,3-disubstituted isoquinoline N-oxides
  作者：Qiuping Ding、Dan Wang、Xiaoyan Sang、Yuqing Lin、Yiyuan Peng

  DOI：10.1016/j.tet.2012.08.039

  日期：2012.10

  A one-pot two-step reaction of 2-alkynylbenzaldoximes with aryl halides has been developed, which offers the 1-position arylated 1,3-disubstituted isoquinoline N-oxides in moderate to good yields in most cases. The isoquinoline N-oxide intermediate was prepared in situ without isolation.

  已经开发了2-炔基苯甲肟与芳基卤化物的一锅两步反应，该反应在大多数情况下以中等至良好的产率提供了1-位芳基化的1,3-二取代的异喹啉N-氧化物。无需分离即可原位制备异喹啉N-氧化物中间体。
• Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations
  作者：Yuanyuan An、Hongguang Xia、Jie Wu

  DOI：10.1039/c6cc03650c

  日期：——

  A base-controlled [3+3] cycloaddition reaction of isoquinoline N-oxides with azaoxyallyl cations is developed. 1,11b-Dihydro-[1,2,4]oxadiazino[3,2-a]isoquinolin-2(3H)-ones are obtained when isoquinoline N-oxides are treated with [small alpha]-halohydroxamates in the presence of sodium carbonate, while...

  开发了碱控制的异喹啉N-氧化物与氮杂烯丙基阳离子的[3 + 3]环加成反应。当在钠的存在下用[小α]-卤代异羟肟酸酯处理异喹啉N-氧化物时，得到1,11b-二氢-[1,2,4]恶二嗪基[3,2-a]异喹啉-2（3H）-。碳酸盐，而...
• Regioselective Decarboxylative Cross-Coupling of Carboxy Isoquinoline <i>N</i>-Oxides
  作者：Jean-Baptiste E. Y. Rouchet、Cédric Schneider、Corinne Fruit、Christophe Hoarau

  DOI：10.1021/acs.joc.5b00475

  日期：2015.6.5

  A straightforward method for direct decarboxylative arylation of 1- and 3-carboxy isoquinaldic acid N-oxides with aryl iodides is reported. The reaction proceeded selectively at the carboxy function site to exclusively give the corresponding C-(1) or C-(3) arylated product. This methodology tolerates various aryl iodides substituted by electronically different groups. Combined with subsequent Reissert-Henze chlorination and SNAr amination, the decarboxylative arylation provides an efficient access to 1,3-functionalized isoquinoline-based antitumor agent.