N-(2-cyanoethyl)azetidine | 17168-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: N-(2-cyanoethyl)azetidine
• 英文别名: N-β-cyanoethyltrimethyleneimine；1-azetidinepropiononitrile；3-(Azetidin-1-yl)propanenitrile
• CAS: 17168-23-9
• 化学式: C₆H₁₀N₂
• 分子量: 110.159
• InChiKey: MMEYPUBJSHNJEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-cyanoethyl)azetidine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以83%的产率得到1-氮杂丁烷丙胺
  参考文献：
  名称：

  Reactions of complexed small nitrogen heterocycles

  摘要：

  Complexes of ethyleneimine and trimethyleneimine have been examined. Their thermal reactions are strictly controlled, giving polyamine complexes, which can also be obtained directly from the polyamines.

  DOI：

  10.1007/bf00961699
• 作为产物：
  描述：

  杂氮环丁烷 、 丙烯腈 生成 N-(2-cyanoethyl)azetidine
  参考文献：
  名称：

  Process for the production of high energy materials

  摘要：

  生产高能硝酸酯的过程涉及在惰性有机溶剂中，将来自环氧烷、环氧乙烷、N-取代环氧丙烷和N-取代环氧丁烷的杂环化合物与N.sub.2 O.sub.4或N.sub.2 O.sub.5反应，当该化合物与N.sub.2 O.sub.4反应时，将产物中的O-或N-硝酸酯取代基氧化为O-或N-硝酸酯取代基。杂环化合物上剩余的环碳原子可以是取代的或未取代的。化合物上的C和/或N环原子的首选取代基团包括烷基、氰基烷基、卤代烷基、硝基烷基和取代芳基。还提供了几种新型硝酸酯，包括聚丁二烯的硝化衍生物，其中聚合物中1%至25%的碳原子被邻位硝酸酯(--ONO.sub.2)基取代。

  公开号：

  US04985584A1

文献信息

• Process for the production of high energy materials
  申请人：Secretary of State for Defence

  公开号：US04985584A1

  公开（公告）日：1991-01-15

  A process for the production of a high energy nitrate ester involves reacting, in an inert organic solvent, a heterocyclic compound, selected from oxiranes, oxetanes, N-substituted aziridines and N-substituted azetidines, with either N.sub.2 O.sub.4 or N.sub.2 O.sub.5, and when the compound is reacted with N.sub.2 O.sub.4, oxidizing the O- or N-nitrate substituents or substituent in the product to O- or N-nitrate substituent or substituents. The remaining ring carbon atoms on the heterocyclic compound may be substituted or unsubstituted. Preferred substituent groups for the C and/or N ring atoms on the compound include alkyl, cyanoalkyl, haloalkyl, nitroalkyl, and substituted aryl. Several novel nitrate ester are also provided, including nitrated derivatives of polybutadiene, in which between 1% and 25% of the carbon atoms in the polymer are substituted by vicinal nitrate ester (--ONO.sub.2) groups.

  生产高能硝酸酯的过程涉及在惰性有机溶剂中，将来自环氧烷、环氧乙烷、N-取代环氧丙烷和N-取代环氧丁烷的杂环化合物与N.sub.2 O.sub.4或N.sub.2 O.sub.5反应，当该化合物与N.sub.2 O.sub.4反应时，将产物中的O-或N-硝酸酯取代基氧化为O-或N-硝酸酯取代基。杂环化合物上剩余的环碳原子可以是取代的或未取代的。化合物上的C和/或N环原子的首选取代基团包括烷基、氰基烷基、卤代烷基、硝基烷基和取代芳基。还提供了几种新型硝酸酯，包括聚丁二烯的硝化衍生物，其中聚合物中1%至25%的碳原子被邻位硝酸酯(--ONO.sub.2)基取代。
• Preparation of nitramine-nitrates by ring-opening nitration of azetidines by dinitrogen pentoxide (N2O5)
  作者：Peter Golding、Ross W. Millar、Norman C. Paul、David H. Richards

  DOI：10.1016/0040-4020(95)98704-l

  日期：1995.4

  of substituents on the ring nitrogen, were treated with N2O5 in chlorinated solvents at sub-ambient temperature and in certain cases formed 1,3-nitramine-nitrate products by a novel ring-opening nitration reaction analogous to that established for aziridines. Yields of the nitramine-nitrates, where ring-opening took place, were generally moderate to high (41–88%), but azetidines bearing N-acyl substituents

  在低于室温的温度下，在氯化溶剂中用N 2 O 5处理11个在环氮上带有各种取代基的氮杂环丁烷，在某些情况下，通过类似的新型开环硝化反应，形成1，3-硝胺-硝酸盐产物。到建立氮丙啶的水平。发生开环的硝酸硝胺硝酸盐的收率通常为中到高（41–88％），但带有N-酰基取代基（乙酰基，丁酰基或氨基甲酰基）的氮杂环丁烷则进行环外取代基的硝化反应以形成N -硝基氮杂环丁烷。同样，带有强吸电子基团（如苦味酚）的氮杂环丁烷对N 2 O 5呈惰性。与氮丙啶相比，氮杂环丁烷的不同反应性是根据四元环化合物的降低的环应变来合理化的。
• Nitration by oxides of nitrogen, part 2 : preparation of nitramines by reaction of strained-ring nitrogen heterocycles with dinitrogen pentoxide
  作者：P Golding、R W Millar、N C Paul、D H Richards (deceased)

  DOI：10.1016/0040-4039(88)85273-0

  日期：——

  Several aziridines and three azekidines have been found to yield nitramine-nitrates in good to excellent yield by ring opening with dinitrogen pentoxide.

  已经发现几种氮丙啶和三种氮杂环丁烷通过与五氧化二氮开环以良好或优异的产率产生硝酸硝胺。
• Amine compounds, resist compositions and patterning process
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20020115018A1

  公开（公告）日：2002-08-22

  Amine compounds having a cyano group are useful in resist compositions for preventing a resist film from thinning and also for enhancing the resolution and focus margin of resist.

  具有氰基的胺类化合物在抗蚀剂组成物中非常有用，可以防止抗蚀膜变薄，并增强抗蚀的分辨率和聚焦余量。
• A process for the production of high energy material
  申请人：Secretary of State for Defence in Her Britannic Majesty's Gov. of the United Kingdom of Great Britain and Northern Ireland

  公开号：EP0223440B1

  公开（公告）日：1991-03-06