tert-butylimino-2-pyrrolidine | 1255658-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: tert-butylimino-2-pyrrolidine
• 英文别名: tert-butyl-iminopyrrolidine；N-tert-butyl-3,4-dihydro-2H-pyrrol-5-amine
• CAS: 1255658-68-4
• 化学式: C₈H₁₆N₂
• mdl: MFCD21641048
• 分子量: 140.228
• InChiKey: MPCNIKBILMEHEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butylimino-2-pyrrolidine 、 copper(l) chloride 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以63.9%的产率得到copper(I) tert-butyl-imino-2-pyrrolidinate
  参考文献：
  名称：

  Copper Iminopyrrolidinates: A Study of Thermal and Surface Chemistry

  摘要：

  Several copper(I) iminopyrrolidinates have been evaluated by thermogravimetric analysis (TGA) and solution based H-1 NMR studies to determine their thermal stability and decomposition mechanisms. Iminopyrrolidinates were used as a ligand for copper(I) to block previously identified decomposition routes of carbodiimide deinsertion and beta-hydrogen abstraction. The compounds copper(I) isopropyl-iminopyrrolidinate (1) and copper(I) tert-butyl-iminopyrrolidinate (2) were synthesized for this study, and compared to the previously reported copper(I) tert-butyl-imino-2,2-dimethylpyrrolidinate (3) and the copper(I) guanidinate [Me2NC((PrN)-Pr-1)(2)Cu](2) (4). Compounds 1 and 2 were found to be volatile yet susceptible to decomposition during TGA. At 165 degrees C in C6D6, they had half-lives of 181.7 h and 23.7 h, respectively. The main thermolysis product of 1 and 2 was their respective protonated iminopyrrolidine ligand. beta-Hydrogen abstraction was proposed for the mechanism of thermal decomposition. Since compound 3 showed no thermolysis at 165 degrees C, it was further studied by chemisorption on high surface area silica. It was found to eliminate an isobutene upon chemisoption at 275 degrees C. Annealing the sample at 350 degrees C showed further evidence of the decomposition of the surface species, likely eliminating ethene, and producing a surface bound methylene diamine.

  DOI：

  10.1021/ic3021035
• 作为产物：
  描述：

  2-吡咯烷酮 、 叔丁胺 在 四磷十氧化物 、 sodium hydroxide 作用下， 以 水 为溶剂， 以30%的产率得到tert-butylimino-2-pyrrolidine
  参考文献：
  名称：

  铝的异亚氨基吡咯烷酸盐†

  摘要：

  一系列 亚氨基吡咯烷（ip）化合物以极高的收率合成，作为用于原子层沉积的新型有机金属前体的潜在配体。这些配体背后的想法是碳二亚胺 （CDI）不会出现四元解插 碳被束缚于一种螯合氮。对我们有利的是，ip配体中的熔点趋势很明显，并且在ip配体与TMA 或者 茶。烷烃消除反应在室温下发生，以高收率得到清洁的产物。收集化合物7 [ipipAlMe 2 ]，12 [tbipAlMe 2 ]和14 [sbipAlEt 2 ]的晶体结构，表明杂多铝物种为二聚体。在每种化合物收集的质谱图中也很明显，因为母峰是二聚体峰减去甲基峰。对所有ipAlMe 2进行了热解研究种观察几天内在等温线下的分解。监测甲基峰的衰减，以其相对于溶液中TMS的比率进行监测，并显示为一级分解。从这些研究中可以明显看出，nbip（9），iso-bip（10）和tbip（12）是最稳定的复合物，半衰期分别为24.8、9.00和10.3天。

  DOI：

  10.1039/c0dt00267d

文献信息

• 2H-PYRROL-5-AMINE DERIVATIVES AS ALPHA ADRENERGIC RECEPTOR MODULATORS
  申请人：ALLERGAN, INC.

  公开号：EP2486009B1

  公开（公告）日：2019-08-21
• KR2023/158682
  申请人：——

  公开号：——

  公开（公告）日：——
• Heteroleptic iminopyrrolidinates of aluminium
  作者：Yamile A. Wasslen、Agnieszka Kurek、Paul A. Johnson、Taylor C. Pigeon、Wesley H. Monillas、Glenn P. A. Yap、Seán T. Barry

  DOI：10.1039/c0dt00267d

  日期：——

  products with high yields. Crystal structures were collected for compounds 7 [ipipAlMe2], 12 [tbipAlMe2], and 14 [sbipAlEt2] demonstrating that the heteroleptic aluminium species were dimers. This was also evident in the mass spectra collected for each compound as the parent peak was that of the dimer minus a methyl. Thermolysis studies were carried out on all the ipAlMe2 species to observe the decomposition

  一系列 亚氨基吡咯烷（ip）化合物以极高的收率合成，作为用于原子层沉积的新型有机金属前体的潜在配体。这些配体背后的想法是碳二亚胺 （CDI）不会出现四元解插 碳被束缚于一种螯合氮。对我们有利的是，ip配体中的熔点趋势很明显，并且在ip配体与TMA 或者 茶。烷烃消除反应在室温下发生，以高收率得到清洁的产物。收集化合物7 [ipipAlMe 2 ]，12 [tbipAlMe 2 ]和14 [sbipAlEt 2 ]的晶体结构，表明杂多铝物种为二聚体。在每种化合物收集的质谱图中也很明显，因为母峰是二聚体峰减去甲基峰。对所有ipAlMe 2进行了热解研究种观察几天内在等温线下的分解。监测甲基峰的衰减，以其相对于溶液中TMS的比率进行监测，并显示为一级分解。从这些研究中可以明显看出，nbip（9），iso-bip（10）和tbip（12）是最稳定的复合物，半衰期分别为24.8、9.00和10.3天。
• Copper Iminopyrrolidinates: A Study of Thermal and Surface Chemistry
  作者：Jason P. Coyle、Peter J. Pallister、Agnieszka Kurek、Eric R. Sirianni、Glenn P. A. Yap、Seán T. Barry

  DOI：10.1021/ic3021035

  日期：2013.1.18

  Several copper(I) iminopyrrolidinates have been evaluated by thermogravimetric analysis (TGA) and solution based H-1 NMR studies to determine their thermal stability and decomposition mechanisms. Iminopyrrolidinates were used as a ligand for copper(I) to block previously identified decomposition routes of carbodiimide deinsertion and beta-hydrogen abstraction. The compounds copper(I) isopropyl-iminopyrrolidinate (1) and copper(I) tert-butyl-iminopyrrolidinate (2) were synthesized for this study, and compared to the previously reported copper(I) tert-butyl-imino-2,2-dimethylpyrrolidinate (3) and the copper(I) guanidinate [Me2NC((PrN)-Pr-1)(2)Cu](2) (4). Compounds 1 and 2 were found to be volatile yet susceptible to decomposition during TGA. At 165 degrees C in C6D6, they had half-lives of 181.7 h and 23.7 h, respectively. The main thermolysis product of 1 and 2 was their respective protonated iminopyrrolidine ligand. beta-Hydrogen abstraction was proposed for the mechanism of thermal decomposition. Since compound 3 showed no thermolysis at 165 degrees C, it was further studied by chemisorption on high surface area silica. It was found to eliminate an isobutene upon chemisoption at 275 degrees C. Annealing the sample at 350 degrees C showed further evidence of the decomposition of the surface species, likely eliminating ethene, and producing a surface bound methylene diamine.