1,3-dimethylperimidinium iodide | 37471-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,3-dimethylperimidinium iodide
• 英文别名: 1,3-dimethylperimidin-3-ium;iodide
• CAS: 37471-37-7
• 化学式: C₁₃H₁₃N₂*I
• 分子量: 324.164
• InChiKey: XTUWHPOGXDAMOY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dimethylperimidinium iodide 在 ammonium hexafluorophosphate 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 chloro(dicarbonyl)(1,3-dimethylperimidin-2-ylidene)iridium(I)
  参考文献：
  名称：

  Converting a perimidine derivative to a cationic N-heterocyclic carbene

  摘要：

  The synthesis and reactivity of the new cationic N-heterocyclic carbene 6 comprising a Cp*Ru+ fragment attached to the aromatic backbone of 1,3-dimethylperimidin-2-ylidene is reported. Carbene 6 forms Rh and Ir complexes of the type [(cod)ClM(6)](+) and [(CO)(2)ClM(6)](+). The analogous complexes of the neutral perimidin-2-ylidene 9 were prepared for comparison purposes. TEP values for both NHCs were calculated from the IR spectra of the carbonyl complexes. The TEP of the cationic carbene 6 (2062 cm(-1)) is shifted to higher wavenumbers compared to the neutral derivative 9 (2057 cm(-1)) indicating that the former ligand is a poorer overall donor. In addition, DFT calculations revealed a reduced HOMO-LUMO gap for the cationic system suggesting an increased pi-acceptor character. Crystal structures of the related complexes [IrCl(cod)NHC(L)] with L = 6 and 9 were determined by X-ray diffraction and show only marginal differences in the geometrical parameters. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.10.047
• 作为产物：
  描述：

  1,3-dimethyl-2,3-dihydro-1H-perimidine 在 2-碘代丙烷 作用下， 反应 1680.0h， 以93%的产率得到1,3-dimethylperimidinium iodide
  参考文献：
  名称：

  摘要：

  Alkylation of N,N'-dimethyl-1,8-diaminonaphthalene with 2-iodopropane in a KOH-DMSO system afforded a new "proton sponge," viz., N,N'-diisopropyl-N,N'-dimethyl-1,8-diaminonaphthalene; the rotation barrier of the Pr-i groups about the N-C bond is 68.4 +/- 0.4 kJ mol(-1) (DMSO).

  DOI：

  10.1023/a:1022449827004

文献信息

• A Chemical-Biological Evaluation of Rhodium(I)<i>N</i>-Heterocyclic Carbene Complexes as Prospective Anticancer Drugs
  作者：Luciano Oehninger、Laura Nadine Küster、Claudia Schmidt、Alvaro Muñoz-Castro、Aram Prokop、Ingo Ott

  DOI：10.1002/chem.201302819

  日期：2013.12.23

  organometallics. A series of RhI‐NHC derivatives with 1,5‐cyclooctadiene and CO as secondary ligands were synthesized, characterized, and biologically investigated as prospective antitumor drug candidates. Pronounced antiproliferative effects were noted for all complexes, along with moderate inhibitory activity of thioredoxin reductase (TrxR) and efficient binding to biomolecules (DNA, albumin). Biodistribution

  带有N杂环卡宾（NHC）配体的铑（I）配合物已广泛用于催化化学中，但很少有关于这些有机金属的生物学性质的报道。一系列的Rh I以1,5-环辛二烯和CO为二级配体的-NHC衍生物进行了合成，表征和生物学研究，作为潜在的抗肿瘤药物候选物。注意到所有复合物均具有明显的抗增殖作用，同时还具有中等程度的硫氧还蛋白还原酶（TrxR）抑制活性和与生物分子的有效结合（DNA，白蛋白）。生物分布研究表明，白蛋白的存在降低了细胞的吸收并证实了铑向核内的转运。在野生型和柔红霉素或长春新碱耐药的Nalm-6白血病细胞中，观察到线粒体膜电位（MMP）的变化以及DNA片段化。总体而言，这些研究表明Rh I‐NHC片段可以用作新抗肿瘤药物的部分结构，尤其是在那些设计用于治疗耐药性恶性组织的药物中。
• Sterically Hindered <i>N</i> -Heterocyclic Salts Utilized as Antimicrobial Agents
  作者：Slindile N. P. Ndlovu、Halliru Ibrahim、Muhammad D. Bala

  DOI：10.1002/jhet.2992

  日期：2017.11

  By the adoption of annulated ring systems for their steric bulkiness, a new series of symmetric N‐heterocyclic imidazolium and perimidium salts were synthesized. Also, corresponding asymmetric ferrocenyl N‐functionalized series were prepared as salts. All the reported salts were fully characterized. The reported X‐ray structure of 4,5‐diphenyl‐1,3‐dimethyl‐1H‐imidazol‐3‐ium iodide (2a) shows that it

  通过采用环状环系统的空间体积，合成了一系列新的对称N杂环咪唑鎓和per鎓盐。此外，相应的不对称二茂铁基N-官能化系列也被制备为盐。所有报道的盐均已充分表征。报道的4,5-二苯基-1,3-二甲基-1 H-咪唑-3-碘化碘（2a）的X射线结构表明它在正交空间群P 2 1 2 1 2 1中结晶。两组盐对金黄色葡萄球菌的重要临床分离株均观察到低至中等的抗菌活性，枯草芽孢杆菌，粪肠球菌和大肠杆菌，铜绿假单胞菌和肠沙门氏菌。结果以美罗培南为基准。1,3-丙基-1H-菲[9,10 - d ]咪唑-3-碘化钾（3b）和1-二茂铁基-3-丙基-1 H -perimidin-3-碘化碘（9b）对所有测试的革兰氏阳性细菌菌株均显示出较高的抗菌活性，最低抑菌浓度范围为8至4μg/ mL（美洛培南= 0.5-0.125μg/ mL），而所有盐对革兰氏阳性菌几乎没有或没有活性。阴性细菌菌株。通常，不对称含二茂铁基的盐比对称盐具有更高的活性。
• <i>N</i>-Heterocyclic Carbenes:  Synthesis, Structures, and Electronic Ligand Properties^,
  作者：Wolfgang A. Herrmann、Jan Schütz、Guido D. Frey、Eberhardt Herdtweck

  DOI：10.1021/om0600801

  日期：2006.5.1

  N-Heterocyclic carbene (NHC) rhodium(l) complexes of general formula Rh(COD)X(NHC) are synthesized and structurally characterized (spectroscopy, X-ray diffraction). The relative sigma-donor/pi-acceptor quality of various NHC ligands was examined and classified by means of IR spectroscopy at the corresponding Rh(CO)(2)I(NHC) complexes. The first single-crystal X-ray diffraction studies of rhodium pyrazolin- and tetrazolinylidene complexes are reported. A wide variety of different azolium salts was applied to obtain rhodium and iridium complexes with two and four carbene ligands.
• Free radicals in the perimidine series. 2-Tert-butylperimidyl radicals
  作者：V. Kh. Sabanov、E. S. Klimov、I. V. Bogdanova、E. P. Trub、N. T. Berberova、O. Yu. Okhlobistin

  DOI：10.1007/bf00522741

  日期：1986.7
• POZHARSKIJ A. F.; KURASOV L. A.; KUZMENKO V. V.; POPOVA L. L., ZH. ORGAN. XIMII, 1981, 17, HO 5, 1005-1013
  作者：POZHARSKIJ A. F.、 KURASOV L. A.、 KUZMENKO V. V.、 POPOVA L. L.

  DOI：——

  日期：——