5-Oximinohexanenitrile | 14274-33-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-Oximinohexanenitrile
• 英文别名: 5-Oximino-capronitril；5-Oximinocapronitrile；5-hydroxyiminohexanenitrile
• CAS: 14274-33-0
• 化学式: C₆H₁₀N₂O
• 分子量: 126.158
• InChiKey: IKMHJYRPMQBWNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Oximinohexanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1,5-diaminohexane
  参考文献：
  名称：

  Notiz zur Darstellung aliphatischer Diamine

  摘要：

  本文没有摘要。

  DOI：

  10.1002/cber.19660991045
• 作为产物：
  描述：

  5-酮基已腈 在 sodium hydroxide 、 硫酸羟胺 作用下， 反应 2.0h， 以84%的产率得到5-Oximinohexanenitrile
  参考文献：
  名称：

  Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles

  摘要：

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

  DOI：

  10.1021/jo00056a021

文献信息

• Selective preparation of linear pentane-1,5-diamines in increased yields
  申请人：BASF Aktiengesellschaft

  公开号：US05344983A1

  公开（公告）日：1994-09-06

  Process for preparing a pentane-1,5-diamine of the formula ##STR1## where R.sup.1 represents a variety of organic radicals including alkyl which can bear substituents such as hydroxyl, halogen, alkoxy, carbalkoxy, carboxyl, alkylamino, cycloalkyl or aryl, and R.sup.2 and R.sup.3 independently of one another, represent hydrogen or have the same meanings as R.sup.1 or together are a C.sub.4 -C.sub.7 -alkylene chain which is unsubstituted or substituted by one to five C.sub.1 -C.sub.4 -alkyl groups, which comprises: (a) reacting a .gamma.-cyanoketone of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above, with excess ammonia in a first reaction space on an acidic heterogeneous catalyst at 20.degree.-150.degree. C. and 15-500 bar, and (b) hydrogenating the resulting reaction product in a second separate reaction space in the presence of excess ammonia on a cobalt, nickel or noble metal catalyst at 50.degree.-180.degree. C. and 30-500 bar. Novel pentane-1,5-diamines are obtained, in which R.sup.1 must contain at least two carbon atoms if R.sup.2 and R.sup.3 are both hydrogen. These new compounds containing two primary amine groups possess advantageous properties of lower volatility and also greater asymmetry (with different reactivity of the two amine functions). They provide useful curing agents for epoxides and act as improved components of polyamides.

  制备式为##STR1##的戊烷-1,5-二胺的过程，其中R1代表各种有机基团，包括可以带有氢氧基、卤素、烷氧基、羧甲氧基、羧基、烷基氨基、环烷基或芳基等取代基的烷基；R2和R3独立地代表氢，或者具有与R1相同的含义，或者一起是未取代或取代了1-5个C1-C4烷基基团的C4-C7烷基链，其包括：(a)在20℃-150℃和15-500巴的酸性异相催化剂的第一反应空间中，用过量氨反应式为##STR2##的γ-氰酮，其中R1、R2和R3具有上述给定的含义；(b)在第二个单独的反应空间中，在过量氨的存在下，在钴、镍或贵金属催化剂的存在下，将所得的反应产物加氢，在50℃-180℃和30-500巴下进行。得到了新的戊烷-1,5-二胺，其中如果R2和R3都是氢，则R1必须至少含有两个碳原子。这些具有两个主要胺基的新化合物具有较低挥发性和更大的不对称性（两个胺基的反应性不同）的优越性质。它们是环氧树脂的有用固化剂，并作为聚酰胺的改进组分。
• Notiz zur Darstellung aliphatischer Diamine
  作者：Giulio Vita、Giuseppe Bucher

  DOI：10.1002/cber.19660991045

  日期：1966.10

  No abstract is available for this article.

  本文没有摘要。
• Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles
  作者：Robert J. Vijn、Henricus J. Arts、Peter J. Maas、Anna M. Castelijns

  DOI：10.1021/jo00056a021

  日期：1993.2

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).