2-hydroxyaminocycloheptanone oxime | 13757-35-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-hydroxyaminocycloheptanone oxime
• 英文别名: N-<1-Oximinocycloheptyl-(2)>-hydroxylamin；Hydroxyaminocycloheptanone oxime；N-[2-(hydroxyamino)cycloheptylidene]hydroxylamine
• CAS: 13757-35-2
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: KLLYZCXVMQVVFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxyaminocycloheptanone oxime 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1,3-dihydroxy-4,5-pentamethyleneimidazolidine
  参考文献：
  名称：

  Synthesis of aliphatic 1,2-bishydroxylamines from 1,3- dihydroxyimidazolidines.

  摘要：

  Reduction of 1-hydroxy-3-imidazoline-3-oxides with NaBH4 gives 1,3-dihydroxyimidazolidines. The latter on subsequent treatment with NH2OH.HCl in EtOH or in hydrochloric acid afford 1,2-bishydroxylamines. An X-ray study of 1,2-bishydroxylaminocycloalkanes has shown them to be cis-configurated.

  DOI：

  10.1007/bf00698944

文献信息

• Formation of ω-(4-oxo-1,4-dihydropyridin-2-yl)alkanamides in the Beckmann rearrangement of spiro-fused cycloalkanone oximes
  作者：V. A. Savel’ev、A. Ya. Tikhonov、T. V. Rybalova

  DOI：10.1134/s1070428016100134

  日期：2016.10

  ω-(4-Oxo-1,4-dihydropyridin-2-yl)alkanamides were obtained from cycloalkanone oximes spirofused to 4-oxo-6-methyl-1,2,3,4-tetrahydropyridine fragment through the α-carbon atom and C2, respectively, on heating in polyphosphoric acid. The resulting amides were converted to the corresponding acids and methyl esters. Methylation of 5-(6-methyl-4-oxo-1,4-dihydropyridin-2-yl)pentanamide with diazomethane

  ω-（4-Oxo-1,4-二氢吡啶-2-基）烷基酰胺是从通过α-碳原子螺接到4-oxo-6-甲基-1,2,3,4-四氢吡啶片段上的环烷酮肟获得的。 C 2分别在多磷酸中加热。将所得酰胺转化为相应的酸和甲酯。5-（6-甲基-4-氧代-1,4-二氢吡啶-2--2-基）戊酰胺与重氮甲烷甲基化，以4-甲氧基吡啶衍生物为主要产物，少量N-甲基衍生物5-（1， 6-二甲基-4-氧代-1,4-二氢吡啶-2-基）戊酰胺。
• Stable Bicyclic Functionalized Nitroxides: The Synthesis of Derivatives of Aza-nortropinone–5-Methyl-3-oxo-6,8-diazabicyclo[3.2.1]-6-octene 8-oxyls
  作者：Larisa N. Grigor’eva、Alexsei Ya. Tikhonov、Konstantin A. Lomanovich、Dmitrii G. Mazhukin

  DOI：10.3390/molecules26103050

  日期：——

  In recent decades, bicyclic nitroxyl radicals have caught chemists’ attention as selective catalysts for the oxidation of alcohols and amines and as additives and mediators in directed C-H oxidative transformations. In this regard, the design and development of synthetic approaches to new functional bicyclic nitroxides is a relevant and important issue. It has been reported that imidazo[1,2-b]isoxazoles

  在最近的几十年中，双环硝酰基自由基已成为化学家的关注焦点，作为醇和胺氧化的选择性催化剂，以及作为定向CH氧化转化的添加剂和介体。在这方面，新功能双环氮氧化物的合成方法的设计和开发是一个相关且重要的问题。据报道，在乙酰丙酮与具有仲羟基氨基的2-羟基氨基肟缩合过程中形成的咪唑并[1,2- b ]异恶唑在温和的碱性催化条件下被再循环为8-羟基-5-甲基-3-氧代-6。 ，8-二氮杂双环[3.2.1] -6-辛烯。后者包含空间受阻的环N-羟基在丙酮中用二氧化铅氧化后，实际上定量地形成了新的稳定的硝酰基双环基团，它们是2,2,6,6-四甲基-4-氧哌啶-1-氧基（TEMPON）和3-咪唑啉。
• Synthesis of 4,5-Dialkyl-2-perfluoroaryl-1H-imidazol-1-ols and 4,5-Dimethyl-2-perfluoroaryl-1H-imidazoles
  作者：I. A. Os’kina、A. S. Vinogradov、B. A. Selivanov、V. A. Savelyev、V. E. Platonov、A. Ya. Tikhonov

  DOI：10.1134/s1070428021120101

  日期：2021.12

  Abstract Aliphatic α-hydroxyamino oximes reacted with perfluoroaromatic aldehydes to give α-perfluoroaryl nitrones which underwent cyclization in acetic acid with the formation of 4,5-dialkyl-2-perfluoroaryl-1H-imidazol-1-ols. The latter were also obtained directly from aliphatic α-hydroxyamino oximes and perfluoro­aromatic aldehydes in acetic acid without isolation of intermediate nitrones. The reaction

  摘要 脂肪族 α-羟基氨基肟与全氟芳香醛反应生成 α-全氟芳基硝酮，其在乙酸中环化形成 4,5-二烷基-2-全氟芳基-1 H-咪唑-1-醇。后者也直接从乙酸中的脂肪族α-羟基氨基肟和全氟芳族醛获得，而无需分离中间体硝酮。4,5-二甲基-2-全氟芳基-1 H-咪唑-1-醇与氯丙酮反应得到4,5-二甲基-2-全氟芳基-1 H-咪唑。
• 5-(Hydroxymethyl)furfural in the Synthesis of 4,5-Dialkyl-1H-imidazol-1-ols
  作者：I. A. Os’kina、V. I. Krasnov、A. Ya. Tikhonov

  DOI：10.1134/s1070428024020027

  日期：2024.2

  Abstract 5-Hydroxymethylfuran-2-carbaldehyde reacts with aliphatic 1,2-hydroxyamine oximes in methanol to form 4,5-dialkyl-substituted 2-(5-hydroxymethylfuran-5-yl)-1H-imidazol-1-ols.

  摘要 5-羟甲基呋喃-2-甲醛与脂肪族1,2-羟胺肟在甲醇中反应生成4,5-二烷基取代的2-(5-羟甲基呋喃-5-基)-1H-咪唑-1-醇。
• Synthesis and antiviral activity of N-[2-hydroxyiminoalkyl[, N-[2-oxoalkyl]-, and N-[2-hydroxyalkyl]-β-hydroxyaminoacid esters
  作者：A. Ya. Tikhonov、N. N. Voinova、T. I. Reznikova、L. B. Volodarskii、G. V. Vladyako、E. I. Boreko、L. V. Korobchenko

  DOI：10.1007/bf00772905

  日期：1992.5