N-hydroxy[4-methoxy-6-piperidino-1,3,5-triazin-2-yl]nitromethanimine | 1190069-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: N-hydroxy[4-methoxy-6-piperidino-1,3,5-triazin-2-yl]nitromethanimine
• 英文别名: 2-methoxy-4-piperidino-1,3,5-triazine-6-nitrolic acid；N-[(4-methoxy-6-piperidin-1-yl-1,3,5-triazin-2-yl)-nitromethylidene]hydroxylamine
• CAS: 1190069-44-3
• 化学式: C₁₀H₁₄N₆O₄
• 分子量: 282.259
• InChiKey: MINJSWGDNWDKOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-hydroxy[4-methoxy-6-piperidino-1,3,5-triazin-2-yl]nitromethanimine 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以82%的产率得到4-Methoxy-6-piperidin-1-yl-[1,3,5]triazine-2-carbonitrile
  参考文献：
  名称：

  Reactions of trinitromethyl-1,3,5-triazines with triphenylphosphine in the presence of hydrogen donors and a dipolarophile

  摘要：

  2-Dialkylamino-4-methoxy-6-trinitromethyl-1,3,5-triazines reacted with triphenylphosphine in toluene in the presence of primary aliphatic alcohols as proton donors to give the corresponding 6-[hydroxyimino (nitro)methyl)-1,3,5-triazines. Analogous reactions in the presence of prop-2-yn-1-ol at elevated temperature resulted in the formation of [3 + 2]-dipolar cycloaddition products, 3-(1,3,5-triazinyl)-5-hydroxymethylisoxazoles.

  DOI：

  10.1134/s1070428009030166
• 作为产物：
  描述：

  在 甲醇 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以71%的产率得到N-hydroxy[4-methoxy-6-piperidino-1,3,5-triazin-2-yl]nitromethanimine
  参考文献：
  名称：

  Reactions of trinitromethyl-1,3,5-triazines with triphenylphosphine in the presence of hydrogen donors and a dipolarophile

  摘要：

  2-Dialkylamino-4-methoxy-6-trinitromethyl-1,3,5-triazines reacted with triphenylphosphine in toluene in the presence of primary aliphatic alcohols as proton donors to give the corresponding 6-[hydroxyimino (nitro)methyl)-1,3,5-triazines. Analogous reactions in the presence of prop-2-yn-1-ol at elevated temperature resulted in the formation of [3 + 2]-dipolar cycloaddition products, 3-(1,3,5-triazinyl)-5-hydroxymethylisoxazoles.

  DOI：

  10.1134/s1070428009030166

文献信息

• 1,3,5-Triazinenitrolic acids. Synthesis and NO-releasing properties
  作者：V. V. Bakharev、A. A. Gidaspov、E. V. Peresedova、V. G. Granik、N. B. Grigor’ev、V. I. Levina、I. S. Severina、A. Yu. Shchegolev、D. E. Dmitriev、A. B. Sheremetev

  DOI：10.1007/s11172-009-0268-z

  日期：2009.9

  Reactions of salts of 1,3,5-triazine dinitromethyl derivatives with nitrogen dioxide that result mainly in 1,3,5-triazinenitrolic acids are investigated. The behavior of nitrolic acid in electroreduction at a mercury drop electrode at various pH was studied; oxygen was shown to accelerate the process. The promoting effect of nitrolic acids on the activity of soluble guanylate cyclase of human platelets

  研究了 1,3,5-三嗪二硝基甲基衍生物的盐与二氧化氮的反应，主要生成 1,3,5-三嗪硝基酸。研究了硝酸在不同pH值下在汞滴电极上的电还原行为；氧气被证明可以加速这一过程。显示了硝酸对人血小板可溶性鸟苷酸环化酶活性的促进作用。所研究的硝酸是一氧化氮的活性供体，一氧化氮是细胞代谢功能的普遍且重要的调节剂。研究了呋喃烷的 NO 释放特性。
• Reactions of 1,3,5-triazinylnitroformaldoxime 4.* synthesis of (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines
  作者：V. V. Bakharev、A. A. Gidaspov、E. V. Selezneva、V. E. Parfenov、I. V. Ulˈyankina、I. S. Nazarova、Yu. T. Palatova、O. S. Elˈtsov

  DOI：10.1007/s10593-012-0901-x

  日期：2012.1

  5-triazin-2-ylnitroformaldoximes with nitriles leads not to the formation of 1,2,4-oxadiazoles but rather to dimerization of the intermediate 1,3,5-triazinylnitrile oxides to give furoxanes. The reaction of 4-R-6-methoxy-1,3,5-triazin-2-ylnitroformaldoximes with ammonia and amines gives 1,3,5-triazinylamidoximes, which upon acylation and subsequent intramolecular cyclization yield (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

  用腈加热4-R-甲氧基-1,3,5-三嗪-2-基硝基甲醛肟不导致形成1,2,4-恶二唑，而是导致中间体1,3,5-三嗪基腈的二聚反应得到呋喃烷。4-R-6-甲氧基-1,3,5-三嗪-2-基硝基甲醛肟与氨和胺反应生成1,3,5-三叠氮酰胺基肟，酰化后分子内环化收率（5-R-1， 2,4-恶二唑-3-基）-1,3,5-三嗪。
• Reactions of 1,3,5-triazinylnitroformaldoximes 3*. Interaction of 1,3,5-triazinylnitroformaldoximes with malonic acid esters
  作者：V. V. Bakharev、A. A. Gidaspov、E. V. Selezneva、I. V. Ul’yankina、D. B. Krivolapov、I. A. Litvinov、O. S. Eltsov

  DOI：10.1007/s10593-011-0676-5

  日期：2011.2

  The reaction of 6-R-4-methoxy-1,3,5-triazin-2-ylnitroformaldoximes with dimethyl malonate gives the zwitterionic 4-methoxycarbonyl-3-(4-R-6-methoxy-1,3,5-triazin-2-yl)-4,5-dihydroisoxazol-5-ones. X-ray structural analysis has been carried out on the zwitterionic 4-methoxycarbonyl-3-(4-methoxy-6-piperidino-1,3,5-triazin-2-yl)-4,5-dihydroisoxazol-5-one.

  6-R-4-甲氧基-1,3,5-三嗪-2-基硝基甲醛肟与丙二酸二甲酯的反应得到两性离子的4-甲氧基羰基-3-（4-R-6-甲氧基-1,3,5-三嗪-2-基）-4，5-二氢异恶唑-5-酮。已经对两性离子的4-甲氧基羰基-3-（4-甲氧基-6-哌啶子基1,3,5-三嗪-2-基）-4,5-二氢异恶唑-5-酮进行了X射线结构分析。
• Reactions of 1,3,5-triazinylnitro-formaldoximes. 2*. The reaction of 1,3,5-triazinylnitroformaldoximes with monosubstituted acetylenes
  作者：V. V. Bakharev、A. A. Gidaspov、E. V. Peresedova、D. B. Krivolapov、E. V. Mironova、I. A. Litvinov

  DOI：10.1007/s10593-009-0382-8

  日期：2009.9

  1,3,5-Triazinylnitrile oxides were prepared in situ from 2-R-4-R′-1,3,5-triazin-6-ylnitroformaldoximes and were treated with substituted acetylenes to give 3,5-disubstituted isoxazoles. The X-ray data obtained for 5-hydroxymethyl-3-(4′-dimethylamino-2′-methoxy-1,3,5-triazin-6′-yl)isoxazole is discussed.

  由2-R-4-R′-1，3，5-三嗪-6-基硝基甲甲醛肟原位制备1，3，5-三嗪基腈，并用取代的乙炔处理得到3，5-二取代的异恶唑。讨论了获得的5-羟甲基-3-（4'-二甲基氨基-2'-甲氧基-1,3,5-三嗪-6'-基）异恶唑的X射线数据。
• Reactions of 1,3,5-triazinylnitroformaldoximes 5*. Synthesis of 5-R-3-(1,3,5-triazinyl)-4,5-dihydro-isoxazoles
  作者：V. V. Bakharev、A. A. Gidaspov、E. V. Selezneva、O. S. El’tsov

  DOI：10.1007/s10593-012-1076-1

  日期：2012.9

  1,3,5-Triazinylnitrile oxides, formed by heating (2-methoxy-4-R-1,3,5-triazin-6-yl)nitroformaldoximes, react with monosubstituted and 1,1-disubstituted ethylenes with the formation of 3-(1,3,5-triazinyl)-5-monosubstituted and 3-(1,3,5-triazinyl)-5,5-disubstituted 2-isoxazolines. The cycloaddition occurs with high regioselectivity to give exclusively 2-isoxazolines substituted at the positions 3 and 5.