3-(4-{2-[bis-(2-cyanoethyl)amino]ethyl}piperazin-1-yl)propionitrile | 96680-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-{2-[bis-(2-cyanoethyl)amino]ethyl}piperazin-1-yl)propionitrile
• 英文别名: 3-[4-[2-[Bis(2-cyanoethyl)amino]ethyl]piperazin-1-yl]propanenitrile
• CAS: 96680-92-1
• 化学式: C₁₅H₂₄N₆
• 分子量: 288.396
• InChiKey: XZDAPIPMBNXWTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-氨乙基哌嗪 、 丙烯腈 以 甲醇 为溶剂， 以94%的产率得到3-(4-{2-[bis-(2-cyanoethyl)amino]ethyl}piperazin-1-yl)propionitrile
  参考文献：
  名称：

  Synthesis of polyamino nitriles, en route to acylpolyamine neurotoxins, via the regioselective michael cyanoethylation of unprotected polyamines. Unusual behaviour of 1-(2-aminoethyl)piperazine

  摘要：

  The Michael cyanoethylation of 1-(2-aminoethyl)piperazine, 4,4'-methylenebis(cyclohexylamine) and bis(3-aminopropylamine)amine, leading to acrylonitrile free (<100 ppm) polyamino nitriles, as a key step in the synthesis of higher polyamines useful in the synthesis of acylpolyamine neurotoxins, was carried out regioselectively on a multigram scale by careful toning of reaction conditions, without a necessity to protect nitrogen atoms. The higher reactivity of primary amino groups in aliphatic diamines and triamines [as in bis(3-aminopropylamine)amine] was also observed in the cyclic amine, 4,4'-methylenebis(cyclohexylamine), but reversed in 1-(2-aminoethyl)piperazine. The compounds with a dicyanoethylated nitrogen atom were thermally less stable than the monocyanoethylated ones. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.034

文献信息

• Reactions of N-(?-aminoethyl)piperazine and its derivatives
  作者：R. N. Zagidullin

  DOI：10.1007/bf00474237

  日期：1991.3
• [EN] COMPOSITION FOR REMOVAL OF RESIST COMPRISING POLY(CYANOALKYL)ETHYLENEAMINE AND METHOD FOR REMOVAL OF RESIST USING THE COMPOSITION<br/>[FR] COMPOSITION COMPRENANT UNE POLY(CYANOALKYL)ÉTHYLÈNEAMINE SERVANT À ENLEVER UNE RÉSERVE ET PROCÉDÉ SERVANT À ENLEVER UNE RÉSERVE UTILISANT LA COMPOSITION
  申请人：TOSOH CORP

  公开号：WO2008023614A1

  公开（公告）日：2008-02-28

  [EN] Disclosed are: a composition for removing a resist, which has an excellent resist stripping property and causes less damage to a semiconductor or a flat panel display material; and a method for stripping a resist by using the composition. Specifically disclosed is a resist stripping agent comprising a poly(cyanoalkyl)ethyleneamine, wherein the poly(cyanoalkyl)ethyleneamine is preferably at least one member selected from N,N'-bis(2-cyanoethyl)-ethylenediamine, N,N,N'-tris(2-cyanoethyl)ethylenediamine, N,N,N',N'-tetrakis(2-cyanoethyl)ethylenediamine, N,N'-bis(2-cyanoethyl)piperazine, N,N'-bis(2-cyanoethyl)-N''-(2-aminoethyl)piperazine, N,N',N'-tris(2-cyanoethyl)-N''-(2-aminoethyl)piperazine and the like.
  [FR] L'invention concerne : une composition servant à enlever une réserve, et qui a une excellente propriété de décapage de réserve et provoque moins d'endommagement à un semi-conducteur ou une matière d'écran plat ; et un procédé servant à décaper une réserve en utilisant la composition. L'invention concerne précisément un agent de décapage de réserve comprenant une poly(cyanoalkyl)éthylèneamine, ladite poly(cyanoalkyl)éthylèneamine étant de préférence au moins un élément sélectionné parmi la N,N'-bis(2-cyanoéthyl)éthylènediamine, la N,N,N'-tris(2-cyanoéthyl)éthylènediamine, la N,N,N',N'-tétrakis(2-cyanoéthyl)éthylènediamine, la N,N'-bis(2-cyanoéthyl)pipérazine, la N,N'-bis(2-cyanoéthyl)-N"-(2-aminoéthyl)pipérazine, la N,N',N'-tris(2-cyanoéthyl)-N"-(2-aminoéthyl)pipérazine et similaires.
• Synthesis of polyamino nitriles, en route to acylpolyamine neurotoxins, via the regioselective michael cyanoethylation of unprotected polyamines. Unusual behaviour of 1-(2-aminoethyl)piperazine
  作者：Piotr Bałczewski、Remigiusz Żurawiński、Maciej Mikina、Bogdan Dudziński

  DOI：10.1016/j.tet.2009.08.034

  日期：2009.10

  The Michael cyanoethylation of 1-(2-aminoethyl)piperazine, 4,4'-methylenebis(cyclohexylamine) and bis(3-aminopropylamine)amine, leading to acrylonitrile free (<100 ppm) polyamino nitriles, as a key step in the synthesis of higher polyamines useful in the synthesis of acylpolyamine neurotoxins, was carried out regioselectively on a multigram scale by careful toning of reaction conditions, without a necessity to protect nitrogen atoms. The higher reactivity of primary amino groups in aliphatic diamines and triamines [as in bis(3-aminopropylamine)amine] was also observed in the cyclic amine, 4,4'-methylenebis(cyclohexylamine), but reversed in 1-(2-aminoethyl)piperazine. The compounds with a dicyanoethylated nitrogen atom were thermally less stable than the monocyanoethylated ones. (C) 2009 Elsevier Ltd. All rights reserved.