1-[2-(isopropylamino)ethyl]-3,3,5,5-tetramethylpiperazin-2-one | 116481-87-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[2-(isopropylamino)ethyl]-3,3,5,5-tetramethylpiperazin-2-one
• 英文别名: 1-[2-(isopropylamino)ethyl]-3,3,5,5-tetramethyl-2-piperazinone；3,3,5,5-Tetramethyl-1-{2-[(propan-2-yl)amino]ethyl}piperazin-2-one；3,3,5,5-tetramethyl-1-[2-(propan-2-ylamino)ethyl]piperazin-2-one
• CAS: 116481-87-9
• 化学式: C₁₃H₂₇N₃O
• 分子量: 241.377
• InChiKey: HNIRDWBMHTXTHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二叔丁基苯酚 、 丙酮 、 氯仿 、 1-[2-(isopropylamino)ethyl]-3,3,5,5-tetramethylpiperazin-2-one 生成 N-isopropyl-N-[2-(2-keto-3,3,5,5-tetramethyl-1-piperazinyl)ethyl]-2-(3,5-di-t-butyl-4-hydroxyphenyl)-2-methyl-propanamide
  参考文献：
  名称：

  LAI, JOHN T.;SON, PYONG N.

  摘要：

  DOI：

文献信息

• Process for methylating a hindered nitrogen atom in an inert non aqueous-solvent
  申请人：THE B.F. GOODRICH COMPANY

  公开号：EP0429996A2

  公开（公告）日：1991-06-05

  A process for methylating the N4 atom of a polysubstituted piperazine or piperazin-2-one ("PSP") is effective despite using a much smaller molar excess of formaldehyde and formic acid than dictated by a conventional Eschweiler-Clarke reaction. Particularly in a complex amine in which the PSP substituent is connected to a triazine ring which in turn may be connected to a N atom of an acyclic polyamine, the molar ratio of NH groups : HCHO : HCOOH is in the range from about 1:1:1 to 1:1.5:1.5, the amount of HCHO and HCOOH being sufficient to methylate at least the groups of said PSP substituent if the complex amine contains terminal -NH groups. The same range of molar ratio is maintained when the total number of NH groups to be methylated includes the terminal -NH groups. The effectiveness of the process is attributed to use of an alkylbenzene solvent in which reaction with only a slight excess of HCHO and HCOOH proceeds apace, and in which solvent the methylated product remains dissolved. The excess HCOOH is neutralized with aqueous alkali. When the solution of methylated product is washed with water, the partition coefficient is at least 0.90 and typically 0.99, so that less than 1% of methylated product is lost in the aqueous wash. More than 90% yield is obtained by harvesting the methylated product from the solvent phase alone. The methylated product is precipitated from the alkylbenzene solution by addition of a precipitating agent, such as heptane. The reaction may be carried out under essentially dry conditions with less than 3% water present; or, it may be carried out under wet conditons (less than 30% water).

  一种将多取代哌嗪或哌嗪-2-酮（"PSP"）的 N4 原子甲基化的工艺，尽管使用的甲醛和甲酸的摩尔过量比传统的埃施韦勒-克拉克反应小得多，但却很有效。特别是在 PSP 取代基与三嗪环相连的复合胺中，该三嗪环又可与无环多胺的 N 原子相连，NH 基团 : HCHO : HCOOH 的摩尔比范围约为 1:1:1 至 1:1.5:1.5，HCHO 和 HCOOH 的用量足以至少将所述 PSP 取代基的基团甲基化。 如果复合胺含有末端 -NH 基团，则 HCHO 和 HCOOH 的用量至少足以将所述 PSP 取代基的基团甲基化。当待甲基化的 NH 基团总数包括末端 -NH 基团时，摩尔比的范围保持不变。该工艺之所以有效，是因为使用了一种烷基苯溶剂，在这种溶剂中，只需少量过量的 HCHO 和 HCOOH 即可迅速发生反应，而甲基化产物仍溶解在溶剂中。过量的 HCOOH 用碱水溶液中和。用水洗甲基化产品溶液时，分配系数至少为 0.90，通常为 0.99，因此在水洗过程中损失的甲基化产品不到 1%。仅从溶剂相中提取甲基化产品，可获得 90% 以上的产量。通过加入沉淀剂（如庚烷），可从烷基苯溶液中析出甲基化产物。反应可在基本干燥的条件下进行，水含量低于 3%；也可在湿润的条件下进行（水含量低于 30%）。
• Hybrid process for preparing a tri-substituted triazine
  申请人：THE B.F. GOODRICH COMPANY

  公开号：EP0508181A1

  公开（公告）日：1992-10-14

  The prior art solvent process for the manufacture of an oxo-piperazinyl triazine (PIP-T) compound required carrying out the reaction between an appropriately hindered cyclic amine and cyanuric chloride in the presence of caustic catalyst, in alkylbenzene solution, typically toluene. The chloride ions generated during the reaction, in presence of water present in the reaction zone, produced serious corrosion and resulted in off-color product which had a melt absorptivity greater than 3.5 mL/gm.cm. This "color" in the product made the product generally unmarketable. Another process to make a PIP-T termed "the solventless" process used no toluene solvent, and no caustic but required such a very large excess of amine that the catalytic function of the amine.HCl salt went unnoticed. In the novel process, referred to as the "hybrid" process, this catalytic function allows the use of only as much toluene in the reactor as is needed to keep the product formed and the excess amine in solution, and the use of less than a two-fold molar excess over the molar amount to displace each chlorine atom of the cyanuric chloride. The result is exceptionally high purity and yield with color no greater than that which the marketplace accepts.

  制造氧代哌嗪基三嗪（PIP-T）化合物的现有技术溶剂工艺要求在苛性催化剂存在下，在烷基苯溶液（通常是甲苯）中进行适当受阻环胺和三聚氯氰之间的反应。反应过程中产生的氯离子，在反应区存在水的情况下，产生了严重的腐蚀，导致产品颜色变淡，熔融吸收率大于 3.5 mL/gm.cm。产品中的这种 "颜色 "使产品普遍滞销。另一种制造 PIP-T 的工艺被称为 "无溶剂 "工艺，它不使用甲苯溶剂，也不使用苛性碱，但需要过量的胺，以至于胺盐的催化功能没有被注意到。在被称为 "混合 "工艺的新工艺中，这种催化功能使得反应器中甲苯的用量仅为保持所形成的产品和过量胺在溶液中的用量，而用于置换三聚氯氰的每个氯原子的摩尔过量则不到摩尔过量的两倍。其结果是纯度和产量极高，颜色不超过市场接受的范围。
• [EN] ALKYLATED POLYALKYLENEPOLYAMINES, SUBSTITUTED OXO-PIPERAZINYL-TRIAZINES AND UV LIGHT STABILIZED COMPOSITIONS
  申请人：THE B.F. GOODRICH COMPANY

  公开号：WO1983002943A1

  公开（公告）日：1983-09-01

  (EN) A branched chain polyalkylenepolyamine ("PAPA") amine having plural amine groups including a secondary amine group intermediate terminal primary amine groups and having at least two carbon atoms between each amine group, is reductively alkylated with a ketone to provide a PAPA alkylated only at an unhindered primary amine group. A preselected degree of steric hindrance at amine groups near each end of the chain enables cyclization by the "ketofrom synthesis" by reaction with a ketone in such a manner as to form a polysubstituted piperazinone ("PSP") ring which includes N atoms of proximate primary and secondary amine groups of the alkylated PAPA. The PSP so formed may then be reacted with a reactive triazine ring so that a PSP substituent is linked to the triazine ring through a single N atom and at least two C atoms, to form a 2-oxo-piperazinyl-triazine ("PIP-T"). Oligomers of the PIP-T may be prepared. The PIP-T compounds are excellent stabilizers against ultraviolet (uv) light degradation in light-sensitive synthetic resinous materials. (FR) Une amine polyalkylènepolyamine ("PAPA") à chaîne ramifiée ayant une pluralité de groupes amines, dont un groupe amine secondaire entre des groupes amines primaires terminaux, et ayant au moins deux atomes de carbone entre chaque groupe amine, est alkylée par réduction avec une cétone pour obtenir une PAPA alkylée uniquement au niveau d'un groupe amine primaire non empêché. Un degré présélectionné d'empêchement stérique des groupes amines proches de chaque extrémité de la chaîne rend possible la cyclisation par "synthèse cétoforme" par réaction avec une cétone de façon à former un anneau de pipérazinone polysubstituée ("PSP") qui comprend des atomes N des groupes amines primaires et secondaires proches appartenant à la PAPA alkylée. La PSP ainsi formée peut alors réagir avec un anneau réactif de triazine de sorte qu'un substituant de PSP est lié à l'anneau de triazine par un seul atome N et au moins deux atomes C, formant ainsi une 2-oxo-pipérazynile-triazine ("PIP-T"). Des oligomères de PIP-T peuvent être préparés. Les composés de PIP-T sont des excellents stabilisateurs contre la dégradation provoquée par la lumière ultra-violette (uv) dans des matériaux résineux synthétiques sensibles à la lumière.

  一种分枝链多聚合体胺基("PAPA")，具有多个胺基，其中包括一个次级胺基和多个一级胺基，各胺基之间至少间隔两个碳原子，在与酮发生还原性甲基化后只能在 unhindered 的一级胺基上进行己基化，使得 PAPA 较为稳定。一种在胺基端部附近调整的适当的立体 hindrance，通过与酮反应实现合成水溶性“_polyrimidinone”(PRP) 环的一种反应，称为“酮的合成”，从而形成一种被多次取代的 PIperazineone (PSP)，该结构中含有近邻一级胺基和二级胺基的 N 原子。所形成的 PSP 还可以与与三元环发生反应，使得PSP 基团可以通过单个 N 原子和至少两个 C 原子与三元环连接，从而形成一种具有 2-oxo-PIperazinyl 的三元环(PIp-T，简称为 PIP-T)。可以选择制备 PIP-T 的多聚物。这些 PIP-T 合成物在光敏感聚合物Resin 中对紫外(UV) 灰色化有极好的稳定性。
• N-(substituted cyclic alkyleneimine)-alpha-(3,5-di-alkyl-4-hydroxy-phenyl)-alpha, alpha-dialkyl acetamides
  申请人：The B.F. GOODRICH Company

  公开号：EP0253010B1

  公开（公告）日：1992-12-02
• SUBSTITUTED OXO-PIPERAZINYL-TRIAZINES AND UV LIGHT STABILIZED COMPOSITIONS
  申请人：The B.F. GOODRICH Company

  公开号：EP0101735B1

  公开（公告）日：1986-10-29