2,5-bis(pyrrolidinomethyl)pyrrole

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-bis(pyrrolidinomethyl)pyrrole
• 英文别名: 2,5-bis((pyrrolidin-1-yl)methylene)-1H-pyrrole；2,5-bis(pyrrolidin-1-ylmethyl)-1H-pyrrole
• 化学式: C₁₄H₂₃N₃
• 分子量: 233.357
• InChiKey: PJESCZJYLCJZDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  22.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis(pyrrolidinomethyl)pyrrole 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 lithium 2,5-bis(pyrrolidinomethyl)pyrrolide
  参考文献：
  名称：

  Antimony(iii) and bismuth(iii) amides containing pendant N-donor groups – a combined experimental and theoretical study

  摘要：

  本文介绍了关于含有吡咯核心和挂有氮官能团的锑（III）和铋（III）酰胺衍生物的合成和结构研究。

  DOI：

  10.1039/c4dt02692f
• 作为产物：
  描述：

  1-(吡咯烷-1-基甲基)吡咯烷 、 吡咯 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 118.0h， 以22%的产率得到N,N-二甲基-1-(1H-吡咯-2-基)甲胺
  参考文献：
  名称：

  涉及氨基化合物和被氯硅烷衍生物活化的α-氨基醚的亲核芳香族化合物的曼尼希反应；氯三甲基硅烷催化

  摘要：

  缩醛和α-氨基醚通过与二氯（二甲基）-和三氯（甲基）-硅烷反应生成N，N-二烷基亚甲基铵盐，但氯三甲基硅烷与α-氨基醚相互作用生成亚胺盐，后者的硅烷与缩醛胺不能：使用这些系统可以进行原位曼尼希反应，在使用三甲基氯硅烷和缩醛胺进行反应的情况下，该反应对于硅烷而言可以是催化的。

  DOI：

  10.1039/c39880001161

文献信息

• NNN-Tridentate Pyrrolyl Rare-Earth Metal Complexes: Structure and Catalysis on Specific Selective Living Polymerization of Isoprene
  作者：Lingfang Wang、Dongtao Liu、Dongmei Cui

  DOI：10.1021/om300049h

  日期：2012.9.10

  The acid–base reactions of NNN-tridentate pyrrolyl ligands (HL1: 2,5-bis((pyrrolidin-1-yl)methylene)-1H-pyrrole; HL2: 2,5-bis((piperidino)methylene)-1H-pyrrole) with rare-earth metal tris(alkyl)s, Ln(CH2SiMe3)3(THF)2, afforded the corresponding bis(alkyl) complexes L1Ln(CH2SiMe3)2(THF)x (Ln = Sc, x = 0 (1a); Ln = Y, x = 1 (1b); Ln = Lu, x = 1 (1c)), L2Sc(CH2SiMe3)2 (2a), and L22Ln2(CH2SiMe3)4 (Ln =

  NNN-三齿吡咯基配体的酸碱反应（HL 1：2,5-双（（吡咯烷-1-基）亚甲基）-1 H-吡咯; HL 2：2,5-双（（哌啶子基）亚甲基） -1 H-吡咯）与稀土金属三（烷基）s Ln（CH 2 SiMe 3）3（THF）2，得到相应的双（烷基）配合物L 1 Ln（CH 2 SiMe 3）2（THF） ）x（Ln = Sc，x = 0（1a）; Ln = Y，x = 1（1b）; Ln = Lu，x = 1（1c）），L2 Sc（CH 2 SiMe 3）2（2a）和L 2 2 Ln 2（CH 2 SiMe 3）4（Ln = Y（2b）; Lu（2c）），产量中等至高。X射线衍射分析表明，该配合物钪1A和2A是THF无溶剂的单体，其中的配位体配位到钪3+在κ离子1：κ 2模式中，当钇和镥络合物1B和1C具有与the络合物相同的配体配位几何形状，但为一THF溶剂化物；复杂的图2b，但是，是
• Lithium, magnesium, zinc complexes supported by tridentate pincer type pyrrolyl ligands: Synthesis, crystal structures and catalytic activities for the cyclotrimerization of isocyanates
  作者：Qiao Liu、Zhiqiang Guo、Hongfei Han、Hongbo Tong、Xuehong Wei

  DOI：10.1016/j.poly.2014.08.009

  日期：2015.1

  Lithium, magnesium, zinc complexes incorporating substituted symmetrical tridentate pyrrolyl ligands were synthesized conveniently and their application for the cyclotrimerization of isocyanate to corresponding isocyanurate has been investigated. The reaction of 1 equivalent of 2,5-bis(pyrrolidinomethyl)pyrrole C4H2NH(2,5-CH2NC4H8)(2)} with n-BuLi generated [LiC4H2N(2,5-CH2NC4H8)(2)}](2) (1) in diethyl ether. Treatment of 2 equivalents of C4H2NH(2,5-CH2NC4H8)(2) with MgBu2 or ZnEt2 in THF afforded [Mg(THF)(C4H2N(2,5-CH2NC4H8)(2)}(2)] (2) or [Zn(C4H2N(2,5-CH2NC4H8)(2)}(2)] (3) in high yield, respectively. Compounds 1, 2 and 3 were characterized by H-1 and C-13 NMR spectra and their molecular structures were determined by single crystal X-ray diffraction. Furthermore, compounds 1, 2 and 3 were proved to be moderate to good initiators for cyclotrimerization of isocyanate to the corresponding isocyanurate in diethyl ether. (C) 2014 Elsevier Ltd. All rights reserved.
• Tridentate pyrrolylzinc compounds: Synthesis, structures, reactivities and catalytic cyclotrimerization reaction of isocyanate
  作者：Zhiqiang Guo、Xuehong Wei、Hongbo Tong、Diansheng Liu

  DOI：10.1016/j.jorganchem.2014.11.009

  日期：2015.1

  The reactions of ZnEt2 with NNN-tridentate pincer type pyrrolyl ligands, 2,5-bis((dimethylamino) methylene)- 1H-pyrrole (HL1), 2,5-bis((pyrrolidin-1-yl)methylene)-1H-pyrrole (HL2) and 2,5-bis((piperidino) methylene)-1H-pyrrole (HL3), afford zinc ethyl compounds [C4H2N(2,5-CH2NMe2)(2)]ZnC2H5 (1), [C4H2N(2,5-CH2N(CH2)(4))(2)]ZnC2H5 (2), and [C4H2N(2,5-CH2N(CH2)(5))(2)]ZnC2H5 (3) in highyield. Subjecting 1, 2, 3 with one equivalent of tert-butylphenol in THF generated [C4H2N(2,5-CH2NMe2)(2)]Zn(O-C6H4-4-Bu-t)}(2) (4), [C4H2N(2,5-CH2N(CH2)(4))(2)]Zn(O-C6H4-4-Bu-t)}(2) (5), [C4H2N(2,5-CH2N(CH2)(5))(2)]Zn(O-C6H4-4-Bu-t)}(2) (6), respectively. Each has been characterized by satisfactory C, H and N microanalysis, NMR spectroscopy at ambient temperature, and single crystal X-ray structural analysis. The compounds Et(6)Z-n(6)O(2)[C4H2N(2,5-CH2N(CH2)(4))(2)](2) (7) and Et6Zn6O2[C4H2N(2,5-CH2N(CH2)(5))(2)](2) (8) obtained accidentally from zinc ethyl compounds with traces of water. Each of compound 1-6 has been used as initiator for cyclotrimerization of isocyanate, and the organozinc compound 3 shows moderate reactivity toward the cyclotrimerization of isocyanate in Et2O solvent under mild conditions. (C) 2014 Elsevier B.V. All rights reserved.
• Effects of Metal Coordination on the π-System of the 2,5-Bis-{(pyrrolidino)-methyl}-pyrrole Pincer Ligand
  作者：Christian Maaß、Diego M. Andrada、Ricardo A. Mata、Regine Herbst-Irmer、Dietmar Stalke

  DOI：10.1021/ic401192x

  日期：2013.8.19

  Pincer complexes of 2,5-bis(pyrrolidino)-methyl}-pyrrole with group 14 elements such as germanium, tin, and lead were prepared and fully characterized by X-ray single-crystal analysis, NMR spectroscopy, and mass spectrometry. The structures of the complexes were analyzed and compared to the free and the lithiated ligand to gain insight into the effects of metal coordination on the aromatic system. A further aspect was to elaborate the capability of group 14 metals to interact with the pyrrole it-system. Therefore, electronic structure calculations were carried out with group 14 complexes to better understand the bonding situation and the trends among the group. The changes in the aromaticity of the pyrrole ring upon coordination have been rationalized according to the interaction of the it-system with the metal. The unusual short bond distance observed between germanium and the coordinated pyrrole nitrogen was also assessed.
• Mannich reactions of nucleophilic aromatic compounds involving aminals and α-amino ethers activated by chlorosilane derivatives; catalysis by chlorotrimethylsilane
  作者：Harry Heaney、George Papageorgiou、Robert F. Wilkins

  DOI：10.1039/c39880001161

  日期：——

  with dichloro(dimethyl)- and trichloro(methyl)-silanes, but whereas chlorotrimethylsilane interacts with α-amino ethers to yield iminium salts, the reaction of the latter silane with aminals does not: in situ Mannich reactions may be carried out using these systems, and in the case of the reactions using chlorotrimethylsilane and aminals the reactions can be catalytic with respect to the silane.

  缩醛和α-氨基醚通过与二氯（二甲基）-和三氯（甲基）-硅烷反应生成N，N-二烷基亚甲基铵盐，但氯三甲基硅烷与α-氨基醚相互作用生成亚胺盐，后者的硅烷与缩醛胺不能：使用这些系统可以进行原位曼尼希反应，在使用三甲基氯硅烷和缩醛胺进行反应的情况下，该反应对于硅烷而言可以是催化的。