pyrrole-2,5-biscarbonitrile | 59215-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: pyrrole-2,5-biscarbonitrile
• 英文别名: pyrrole-2,5-dicarbonitrile；2,5-dicyanopyrrole；1H-Pyrrole-2,5-dicarbonitrile
• CAS: 59215-66-6
• 化学式: C₆H₃N₃
• 分子量: 117.11
• InChiKey: AXTFVVDDOGBXBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pyrrole-2,5-biscarbonitrile 在 硫化氢 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 5-<5-(4-formylpyrrol-2-yl)pyrrol-2-yl>pyrrole-3-carbaldehyde
  参考文献：
  名称：

  Photoreaction of Arenecarbothioamides with Furan. Facile Synthesis of Pentagonal Di- and Tri-heterocyclic Compounds

  摘要：

  Irradiation of arenecarbothioamides with furan in methanol gave 2-arylpyrrole derivatives in moderate yields. This reaction was applied to the synthesis of pentagonal di- and tri-heterocyclic compounds.

  DOI：

  10.3987/com-98-s(h)39
• 作为产物：
  描述：

  1H-吡咯-2,5-二甲醛 在 苯酐 、 盐酸羟胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 pyrrole-2,5-biscarbonitrile
  参考文献：
  名称：

  Charging and Deforming the Pybox Ligand: Enantiomerically Pure Double Helices and Their Interconversion

  摘要：

  Reaction of pyrrole-2,5-biscarbonitrile (1) with an excess of (S)or (R)-valinol in boiling chlorobenzene selectively yielded the two enantiomeric bis(oxazolinyl)pyrroles (S,S)-bis[2-(4,4'diisopropyl-4,5-dihydrooxazolyl)]pyrrole ("S,S-iproxpH", 2a) and (R,R)-bis[2(4,4'-diisopropyl-4,5-dihydrooxazolyl)]- pyrrole ("RR-iproxpH", 2b), respectively. Lithiation of 2a and 2b at -78degreesC and reaction with an equimolar amount of [PdCl2(cod)] (cod=1,5-cyclooctadiene) gave the helical dinuclear palladium complexes (M)-[PdCl(S,S-iproxp)](2) (3a) and (P)-[PdCl(S,S-iproxp)](2) (3b) as well as (P)-[PdCl(R,R-iproxp)](2) (4a) and (M)-[PdCl(R,Riproxp)](2) (4b). Reaction of a 1:1 mixture of lithiated 2 a and 2 b with an equimolar amount of [PdCl,(cod)] gave a mixture of the homochiral complexes 3a,b and 4a,b along with the racemic mixture of the heterochiral complex [Pd2Cl2(S,S-iproxp)(R,R-iproxp)] (5). The double helical structure as well as the absolute configuration of these neutral dinuclear palladium complexes was confirmed by X-ray diffraction studies of all five complexes. One of the oxazolyl units and the anionic pyrrolide occupy two coordination sites in an approximately square-planar ligand arrangement at the Pd centers whereas the second oxazolyl ring is twisted out of this plane and binds to the second metal center. The heterochiral complex 5 does not possess any element of molecular symmetry. The P-helical complexes 3b and 4a display a positive CD at 3 10 nm and a weaker negative CD at 350 nm, while the compounds possessing M-helicity have the corresponding mirror image CD spectra. Complexes 3 a and 4 a have an additional weak long wavelength CD feature between 380 and 420 nm which is absent in the spectra of 3 b and 4 b. Upon heating a solution of 3b, interconversion to the diastereomer of opposite helicity 3a sets in, for which a first-order rate law with respect to the concentration of the complex was established; activation parameters: DeltaHdouble dagger=68kJmol(-1), DeltaSdouble dagger= -99 J mol(-1) K-1. A cross-over experiment monitored by H-1 NMR spectroscopy also gave the racemate of the mixed-ligand complex 5: (P)-[Pd2Cl2(S,S-iproxp)(R,R-iproxp)] and (M)[Pd2Cl2(S,S-iproxp)(R,R-iproxp)] indicating an intermolecular exchange involving mononuclear [PdCl(iproxp)) complex fragments.

  DOI：

  10.1002/1521-3765(20020916)8:18<4308::aid-chem4308>3.0.co;2-t

文献信息

• [Bis(oxazolinyl)pyrrole]palladium Complexes as Catalysts in Heck‐ and Suzuki‐Type C−C Coupling Reactions
  作者：Clément Mazet、Lutz H. Gade

  DOI：10.1002/ejic.200390148

  日期：2003.3

  The two bis(oxazoline)pyrrole ligand precursors 2,5-bis(4,4'-dimethyl-4,5-dihydrooxazol-2-yl)pyrrole (dmoxpH, 2) and 2,5-bis(4,4'-dimethyl-4,5-dihydrooxazol-2-yl)-3,4-diethylpyrrole (Et2dmoxpH, 5) have been synthesised and metallated by treatment with n-butyllithium at -78 °C in diethyl ether. Treatment of the lithium pyrrolide with 1.1 mol-equiv. of [PdCl2(COD)] gave the corresponding helical dinuclear

  两种双(恶唑啉)吡咯配体前体2,5-双(4,4'-二甲基-4,5-二氢恶唑-2-基)吡咯(dmoxpH, 2)和2,5-双(4,4'-二甲基-4,5-二氢恶唑-2-基)-3,4-二乙基吡咯 (Et2dmoxpH, 5) 已合成，并通过在 -78 °C 的乙醚中用正丁基锂处理进行金属化。用 1.1 摩尔当量处理吡咯酸锂。[PdCl2(COD)] 生成相应的螺旋双核钯配合物 [Pd2Cl2(dmoxp)2] (6) 和 [Pd2Cl2(Et2dmoxp)2] (7)。在这两种配合物中，三齿双（恶唑啉基）吡咯化物配体桥接两个金属中心，其中一个恶唑啉环和带电的吡咯化物与一个 Pd 中心配位，而第二个恶唑啉环相对于吡咯化物单元扭曲并配位到第二个钯原子。发现配合物 6 和 7 是苯乙烯和丙烯酸乙酯 Heck 偶联反应的活性催化剂的前体，前者的转化率超过 9000，以及二取代的烯烃，如巴豆酸甲酯和肉桂酸甲酯。发现配合物
• Just add tetrazole: 5-(2-Pyrrolo)tetrazoles are simple, highly potent anion recognition elements
  作者：Rebecca J. M. Courtemanche、Thomas Pinter、Fraser Hof

  DOI：10.1039/c1cc15875a

  日期：——

  We report a novel pyrrolo-tetrazole motif that encodes anion binding orders of magnitude stronger than closely related systems and suggests the general utility of amide-tetrazole exchanges for creating simple, high-affinity anion binders.

  我们报告了一种新型吡咯四氮唑基团，它编码的阴离子结合力比密切相关的系统要强几个数量级，并表明酰胺-四氮唑交换在创建简单、高亲和力阴离子结合剂方面具有普遍用途。
• METHOD OF PREPARING ORGANIC POROUS SOLIDS AND SOLIDS OBTAINABLE BY THIS METHOD
  申请人：Antonietti Markus

  公开号：US20100280216A1

  公开（公告）日：2010-11-04

  The present invention relates to a method of preparing porous solids, which method comprises polymerizing, in a salt melt or a eutectic mixture of salt melt containing at least one Lewis acidic salt, cyano monomers having at least one or at least two cyano groups in their molecule, wherein the at least one or at least two cyano groups are bonded to a rigid linking group in the cyano monomer, as well as to the porous solids obtainable by that method. Owing to their porosity and the associated extremely high specific surface area, the porous solids are useful as sorbents, filtering and insulating materials, as well as catalyst carriers.

  本发明涉及一种制备多孔固体的方法，该方法包括在含有至少一种Lewis酸性盐的盐熔体或盐熔体共晶混合物中聚合至少含有一个或至少两个氰基团的氰基单体，其中至少一个或至少两个氰基团与氰基单体中的刚性连接基结合，以及由该方法获得的多孔固体。由于其多孔性和相关的极高比表面积，多孔固体可用作吸附剂、过滤和绝缘材料以及催化剂载体。
• Barnett, Graham H.; Anderson, Hugh J.; Loader, Charles, E., Canadian Journal of Chemistry, 1980, vol. 58, p. 409 - 411
  作者：Barnett, Graham H.、Anderson, Hugh J.、Loader, Charles, E.

  DOI：——

  日期：——
• BARNETT G. H.; ANDERSON H. J.; LOADES C. E., CAN. J. CHEM., 1980, 58, NO 4, 409-411
  作者：BARNETT G. H.、 ANDERSON H. J.、 LOADES C. E.

  DOI：——

  日期：——