4-isoselenocyanate-2,2,6,6-tetramethylpiperidin-1-oxyl | 676614-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-isoselenocyanate-2,2,6,6-tetramethylpiperidin-1-oxyl
• 英文别名: 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl；4-isoselenocyanato-2,2,6,6-tetramethylpiperidin-1-oxyl；4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxy；TEMPO-NCSe
• CAS: 676614-09-8
• 化学式: C₁₀H₁₇N₂OSe
• 分子量: 260.218
• InChiKey: DWNCBUDJOTZJHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  16.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吗啉 、 4-isoselenocyanate-2,2,6,6-tetramethylpiperidin-1-oxyl 以 苯 为溶剂， 以54.3%的产率得到
  参考文献：
  名称：

  氮氧化物的反应，第 7 部分：新型氮氧化物硒脲的合成

  摘要：

  4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl 与选定的胺和低级醇的反应得到相应的新型硒脲和硒氨基甲酸酯，均带有硝酰基部分。一些合成的硒脲和硒氨基甲酸酯对病原真菌显示出中等至良好的活性。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:549–556, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20454

  DOI：

  10.1002/hc.20454
• 作为产物：
  描述：

  4-氨基-TEMPO 在 水 、 甲基三辛基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.75h， 生成 4-isoselenocyanate-2,2,6,6-tetramethylpiperidin-1-oxyl
  参考文献：
  名称：

  Synthesis of Isoselenocyanates

  摘要：

  Isoselenocyanates were synthesized by two methods under phase-transfer conditions (50% aq NaOH, CH2Cl2, Aliquat 336); the first started from isocyanides and selenium and gave isoselenocyanates in 61-89% yields, while the second started from amines and used chloroform and selenium, by applying sequentially the Hofmann isonitrile synthesis and the addition of selenium, in 4-70% yields.

  DOI：

  10.1055/s-0035-1560481

文献信息

• Reactions of nitroxides. Part X: Antifungal activity of selected sulfur and selenium derivatives of 2,2,6,6-tetramethylpiperidine
  作者：Jerzy Zakrzewski、Maria Krawczyk

  DOI：10.1016/j.bmcl.2010.10.092

  日期：2011.1

  The antifungal activity of nitroxyl radicals—derivatives of 2,2,6,6-tetramethylpiperidine-1-oxyl with reactive substituents 4-isothiocyanato-, 4-isocyano-, and 4-isoselenocyanato- and of -formyl-, -thioformyl-, -selenoformyl-derivatives of 2,2,6,6-tetramethylpiperidine was investigated. Those of the above compounds, which contain a sulfur or selenium atom are the most active against four fungus plant

  硝酰自由基的抗真菌活性 - 2,2,6,6-四甲基哌啶-1-氧基的衍生物，带有反应性取代基 4-异硫氰基-、4-异氰基-和 4-异硒氰基-以及 -甲酰基-、-硫代甲酰基-、研究了2,2,6,6-四甲基哌啶的硒代甲酰基衍生物。上述化合物中含有硫或硒原子的化合物对四种真菌植物病原菌最有活性： 、 、 、 。4-Isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl 被证明是最活跃的化合物。
• Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates
  作者：Jerzy Zakrzewski、Bogumiła Huras、Anna Kiełczewska、Maria Krawczyk、Jarosław Hupko、Katarzyna Jaszczuk

  DOI：10.3390/molecules24132457

  日期：——

  The reactions of 3-isoselenocyanato-2,2,5,5-tetramethylpyrrolidine-1-oxyl, 3-isoselenocyanatomethyl-2,2,5,5-tetramethyl-3-pyrrolidine-1-oxyl, and 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl with selected amines and alcohols give the corresponding novel nitroxyl selenoureas and selenocarbamates, all bearing a nitroxyl moiety. Synthesized selenoureas and selenocarbamates show significant

  3-异硒氰基-2,2,5,5-四甲基吡咯烷-1-氧基、3-异硒氰基甲基-2,2,5,5-四甲基-3-吡咯烷-1-氧基和4-异硒氰基-2的反应， 2,6,6-四甲基哌啶-1-氧基与选定的胺和醇产生相应的新型硝酰基硒脲和硒代氨基甲酸酯，它们都带有硝酰基部分。合成的硒脲和硒代氨基甲酸盐对病原真菌和细菌具有显着的活性。与哌啶硝基氧化物相比，吡咯烷、五元硝酰基硒脲和硒代氨基甲酸酯分别对病原真菌和细菌表现出优异的抗真菌和抗菌活性。
• 4-Isocyano-2,2,6,6-tetramethylpiperidin- 1-oxyl:  A Valuable Precursor for the Synthesis of New Nitroxides
  作者：Jerzy Zakrzewski、Julia Jezierska、Jarosław Hupko

  DOI：10.1021/ol036298q

  日期：2004.3.1

  To enrich the limited set of isonitriles typically employed, 4-isocyano-2,2,6,6-teramethylpiperidin-1-oxyl (1) is proposed as an isonitrile bearing a nitroxyl moiety. Isocyanide 1 was used in some reactions characteristic of isonitriles. Isoselenocyanate, amides (products of Passerini and Ugi reactions), and tetrazole derivative were obtained. The EPR spectra of the urea derivative 5b and a product of an Ugi reaction 7 (both dinitroxides) were analyzed.
• Synthesis of Isoselenocyanates
  作者：Jerzy Zakrzewski、Bogumiła Huras、Anna Kiełczewska

  DOI：10.1055/s-0035-1560481

  日期：——

  Isoselenocyanates were synthesized by two methods under phase-transfer conditions (50% aq NaOH, CH2Cl2, Aliquat 336); the first started from isocyanides and selenium and gave isoselenocyanates in 61-89% yields, while the second started from amines and used chloroform and selenium, by applying sequentially the Hofmann isonitrile synthesis and the addition of selenium, in 4-70% yields.
• Reactions of nitroxides, part 7: Synthesis of novel nitroxide selenoureas
  作者：Jerzy Zakrzewski、Maria Krawczyk

  DOI：10.1002/hc.20454

  日期：2008.9

  The reactions of 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl with selected amines and lower alcohols give the corresponding novel selenoureas and selenocarbamates, all bearing the nitroxyl moiety. Some of the synthesized selenoureas and selenocarbamates show moderate-to-good activity against pathogenic fungi. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:549–556, 2008; Published online

  4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl 与选定的胺和低级醇的反应得到相应的新型硒脲和硒氨基甲酸酯，均带有硝酰基部分。一些合成的硒脲和硒氨基甲酸酯对病原真菌显示出中等至良好的活性。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:549–556, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20454