2,5-bis((piperidino)methylene)-1H-pyrrole | 99230-12-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-bis((piperidino)methylene)-1H-pyrrole
• 英文别名: 1-[[5-(piperidin-1-ylmethyl)-1H-pyrrol-2-yl]methyl]piperidine
• CAS: 99230-12-3
• 化学式: C₁₆H₂₇N₃
• 分子量: 261.41
• InChiKey: DJYVYHVSVYCEJR-UHFFFAOYSA-N

物化性质

• 熔点：
  96.5-97 °C
• 沸点：
  374.6±32.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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((piperidino)methylene)-1H-pyrrole 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 2-[5-(氰基甲基)-1H-吡咯-2-基]乙腈
  参考文献：
  名称：

  Flitsch, Wilhelm; Kneip, Heinz-Gerd, Liebigs Annalen der Chemie, 1985, # 9, p. 1895 - 1903

  摘要：

  DOI：
• 作为产物：
  描述：

  二哌啶甲烷 、 吡咯 以 氯仿 为溶剂， 反应 24.0h， 以70%的产率得到2,5-bis((piperidino)methylene)-1H-pyrrole
  参考文献：
  名称：

  Use of Methylene Chloride as a C1 Unit in N,N-Dialkylaminomethylation Reaction

  摘要：

  Mannich products have been isolated in good yields with methylene chloride as a C1 unit, instead of formaldehyde. It is evidenced that, contrary to previous understanding, a high pressure procedure is not necessary required and that the methylene bisamines function as intermediates.

  DOI：

  10.1080/00397919308009843

文献信息

• <i>N</i>-Aminomethylation vs. <i>C</i>-Aminomethylation of Indole and Pyrrole with an <i>N</i>,<i>O</i>-Acetal Controlled by the Hardness of a Counter Ion of an Iminium Compound
  作者：Norio Sakai、Hidetoshi Okano、Kazuyori Shimamura、Takeo Konakahara

  DOI：10.1246/cl.131116

  日期：2014.4.5

  Under relatively strong Lewis acidic conditions (a softer counter ion) using TMSOTf and TMSI, the aminomethylation of indole or pyrrole with a typical N,O-acetal preferentially produced the kinetically favored N-aminomethylated indole or pyrrole derivative. Use of a relatively weak Lewis acid (a harder counter ion), such as TMSCl and TMSBr, preferentially produced the thermodynamically favored C-aminomethylated indole and pyrrole derivative.

  在使用 TMSOTf 和 TMSI 的相对较强的路易斯酸条件下（较软的反离子），吲哚或吡咯与典型的 N,O-缩醛的氨基甲基化反应优先产生动力学上有利的 N-氨基甲基化吲哚或吡咯衍生物。使用相对较弱的路易斯酸（较硬的反离子），如 TMSCl 和 TMSBr，优先产生热力学上有利的 C-氨基甲基化吲哚和吡咯衍生物。
• 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
• Alkylation with Non-ketonic Mannich Bases. Aminothiazoles and Pyrrole
  作者：Noel F. Albertson

  DOI：10.1021/ja01182a069

  日期：1948.2
• The Condensation of Aldehydes and Amines with Nitrogenous Five-atom Ring Systems¹
  作者：G. Bryant Bachman、Lowell V. Heisey

  DOI：10.1021/ja01216a018

  日期：1946.12
• 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.