2-Hydroxylamino-pentansaeurenitril | 5259-70-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Hydroxylamino-pentansaeurenitril
• 英文别名: 2-(Hydroxyamino)pentanenitrile
• CAS: 5259-70-1
• 化学式: C₅H₁₀N₂O
• 分子量: 114.147
• InChiKey: ONKPLQYPOTVDMS-UHFFFAOYSA-N

物化性质

• 熔点：
  95.5-98.5 °C
• 沸点：
  243.9±42.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  56
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydroxylamino-pentansaeurenitril 在 硝酸铵 、 硝酸 、 对苯醌 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 α,α-Dinitro-valeronitril
  参考文献：
  名称：

  The Conversion of Aldoximes to α-Oximinonitriles, α,α-Dinitronitriles, and 1,1-Dinitroparaffins¹

  摘要：

  DOI：

  10.1021/jo01079a001
• 作为产物：
  描述：

  Pentanenitrile, 2-[[(trimethylsilyl)oxy]amino]- 在 甲醇 作用下， 生成 2-Hydroxylamino-pentansaeurenitril
  参考文献：
  名称：

  A NEW ROUTE TO AMINONITRILES VIA CYANOSILYLATION OF SCHIFF BASES AND OXIMES

  摘要：

  研究发现，三甲基硅基氰在少量路易斯酸的催化下，能够与席夫碱和肟反应，以极佳的产率生成N-三甲基硅基-α-氨基腈和N-三甲基硅氧基-α-氨基腈，这些产物易被水解为相应的α-氨基腈和α-羟氨基氰。

  DOI：

  10.1246/cl.1975.331

文献信息

• NN-di-(1-cyanoalkyl)hydroxylamines. Part IV. Isolation of acyclic nitrones and their reaction with hydrogen cyanide
  作者：Masaichiro Masui、Chino Yijima

  DOI：10.1039/j39670002022

  日期：——

  α-Hydroxyamino-nitriles react with aldehydes to give the corresponding crystalline N-alkylidene-N-(1-cyanoalkyl)N-oxides. These acyclic nitrones are monomeric and fairly stable. The reaction of the nitrones with hydrogen cyanide gives NN-di-(1-cyanoalkyl)hydroxylamines almost quantitatively.

  α羟基氨基-腈类与醛反应，得到相应的结晶Ñ -alkylidene- ñ - （1-氰基）ñ -oxides。这些无环硝酮是单体且相当稳定。与氰化氢的硝酮的反应，得到NN -二- （1-氰基烷基）羟胺几乎定量。
• Kinetics of aliphatic nitrone formation on the addition of N-alkyl-hydroxylamines to aliphatic aldehydes in aqueous solution
  作者：Masaichiro Masui、Chino Yijima

  DOI：10.1039/j29660000056

  日期：——

  The formation of aliphatic nitrones from N-cyclohexylhydroxylamine and aldehydes has been followed spectro-photometrically in aqueous buffer solution of pH 1·5–9·4. The reaction is second-order at constant pH, being dependent on the free hydroxylamine concentration and the free aldehyde concentration. The second-order rate constant shows a linear dependence on [H+] below pH 7, but is independent of

  在pH 1·5-9·4的缓冲水溶液中分光光度法跟踪了由N-环己基羟胺和醛形成的脂肪族硝基。该反应在恒定pH下是二级反应，取决于游离羟胺浓度和游离醛浓度。二阶速率常数对pH低于7的[H + ]呈线性依赖性，但与pH 8之上的[H + ]无关。根据反应常数ρ*的值，活化参数ΔS ‡和E a，以及几种羰基反应的已知机理，提出了一种反应方案。中间二醇的形成是一种特定酸催化的反应，在酸性介质中是决定速率的，但是中间二醇的脱水在碱中是决定速率的。
• Pritzkow,W.; Roesler,W., Justus Liebigs Annalen der Chemie, 1967, vol. 703, p. 66 - 76
  作者：Pritzkow,W.、Roesler,W.

  DOI：——

  日期：——
• α-Hydroxylamino Nitriles and α-Hydroxylamino Acids^1,2
  作者：L. NEELAKANTAN、WALTER H. HARTUNG

  DOI：10.1021/jo01101a007

  日期：1958.7
• N-(1-Cyanoalkyl)-N-hydroxyureas
  作者：Rainer Camehn、Klaus Rehse

  DOI：10.1002/(sici)1521-4184(200001)333:1<27::aid-ardp27>3.0.co;2-z

  日期：2000.1

  Nineteen N-(1-cyanoalkyl)-N-hydroxyureas comprising aliphatic (3a-i, 4a, b, and 5a) and aromatic (3j-n, 4c, 5b) compounds were prepared, fourteen of them for the first time, and tested for antithrombotic (p.o. administration to rats, 60 mg/kg) effects. The N-(1-cyanocyclohexyl)-N-hydroxy-N'-phenylurea (3j) was most potent and inhibited laser-induced (35 mW, 50 ms) thrombus formation in arterioles by 21% and that in venules by 15%. The compounds form nitric oxide in vitro by the addition of a Fe3(+)-porphyrin complex and an oxygen donor. Moreover, the most active compound 3j in vivo exhibits the highest NO formation in vitro. Furthermore, it was shown that the cyano group is essential for the desired activities and NO formation. These results suggest that the title compounds act as NO donors.