4,5-dicyano-2-methoxyimidazole | 51850-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dicyano-2-methoxyimidazole
• 英文别名: 2-methoxy-1H-imidazole-4,5-dicarbonitrile
• CAS: 51850-82-9
• 化学式: C₆H₄N₄O
• 分子量: 148.124
• InChiKey: QWZSTGNIUAJGCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-dicyano-2-methoxyimidazole 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 dimethyl 1-methyl-2-methoxyimidazole-4,5-dicarboxylate
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023
• 作为产物：
  描述：

  2-amino-3-(methoxymethylamino)butanedinitrile 以60%的产率得到
  参考文献：
  名称：

  ANDERSON, W. K.;BHATTACHARJEE, D.;HOUSTON, D. M., J. MED. CHEM., 32,(1989) N, C. 119-127

  摘要：

  DOI：

文献信息

• Bis(acyloxmethyl)imidazole compounds
  申请人：The Research Foundation of State University of New York

  公开号：US05329012A1

  公开（公告）日：1994-07-12

  This invention relates to new bis(acyloxymethyl)imidazole derivatives; to compositions comprising these derivatives; and to processes for their utility as fungicides, bactericides and as inhibitors of the growth of cancer, particularly solid tumor cancer, in warm blooded animals of the formula: ##STR1## wherein M is ##STR2## or R; each R, R' and R" are independently selected from hydrogen and Z substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl, aryl, and heterocyclic ring wherein said ring comprises at least one of oxygen, nitrogen, sulfur or silicon; provided that ##STR3## may form a Z substituted or unsubstituted heterocyclic, and R' and R" attached to the imidazole ring, may form a Z substituted or unsubstituted heterocyclic ring; X is selected from at least one of oxygen, sulfur, nitrogen and alkyl; provided further that silicon is not directly attached to oxygen, sulfur or nitrogen and R' is not hydrogen when X is oxygen or sulfur; and Z is selected from halogen, nitro, nitrile, alkyl, haloalkyl, alkenyl, carboxylic acid, carboxylic acid ester, carboxylic acid amide, ether, thioether, hydroxyl, acylated hydroxyl, sulfonylamide, sulfonylurea, sulfoxide, sulfone, substituted and unsubstituted amine or mixtures thereof.

  这项发明涉及新的双(酰氧甲基)咪唑衍生物；包括这些衍生物的组合物；以及作为杀菌剂、杀菌剂和抑制癌症生长的工具的过程，特别是固体肿瘤癌症，在温血动物中的公式：##STR1## 其中M是##STR2##或R；每个R、R'和R"独立地选自氢和Z取代或未取代的烷基、环烷基、环烯烃基、烯基、芳基和杂环戒指，其中所述环至少包括氧、氮、硫或硅中的一个；前提是##STR3##可以形成Z取代或未取代的杂环，并且连接到咪唑环的R'和R"可以形成Z取代或未取代的杂环；X选自氧、硫、氮和烷基中的至少一个；进一步提供的是硅不直接连接到氧、硫或氮，当X为氧或硫时，R'不是氢；Z选自卤素、硝基、腈基、烷基、卤代烷基、烯基、羧酸、羧酸酯、羧酸酰胺、醚、硫醚、羟基、酰化羟基、磺酰胺、磺酰脲、亚砜、砜、取代和未取代胺或其混合物。
• Imidazolium 2-Substituted 4,5-Dicyanoimidazolate Ionic Liquids: Synthesis, Crystal Structures and Structure-Thermal Property Relationships
  作者：Suvendu Sekhar Mondal、Holger Müller、Matthias Junginger、Alexandra Kelling、Uwe Schilde、Veronika Strehmel、Hans-Jürgen Holdt

  DOI：10.1002/chem.201304934

  日期：2014.6.23

  Thirty six novel ionic liquids (ILs) with 1‐butyl‐3‐methylimidazolium and 3‐methyl‐1‐octylimidazolium cations paired with 2‐substitited 4,5‐dicyanoimidazolate anions (substituent at C2=chloro, bromo, methoxy, vinyl, amino, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and phenyl) have been synthesized and characterized by using differential scanning calorimetry

  与1-丁基-3-甲基咪唑鎓和3-甲基-1-辛基咪唑鎓阳离子与2-取代的4,5-二氰基咪唑鎓阴离子配对的36种新型离子液体（IL）（在C2处取代基为氯，溴，甲氧基，乙烯基，氨基，甲基，乙基，丙基，异丙基，丁基，戊基，己基，庚基，辛基，壬基，癸基，十一烷基和苯基）已合成并通过差示扫描量热法（DSC），热重分析（TGA）和单晶进行了表征X射线晶体学。研究和讨论了阳离子和阴离子的类型和结构对所得离子液体（包括几种室温离子液体（RTIL））的热性能的影响。IL显示出大的液体和结晶范围，并且在冷却时以-22至-68℃的玻璃化转变温度形成玻璃。咪唑基阴离子的烷基取代基的作用反映了IL的结晶，熔点和热分解。可以考虑库仑堆积力，范德华力和阴离子的大小来改变热转变。确定了离子液体的三个晶体结构，并研究了阳离子和阴离子的变化对结构堆积的影响。
• Insights into the pores of microwave-assisted metal–imidazolate frameworks showing enhanced gas sorption
  作者：Suvendu Sekhar Mondal、Subarna Dey、Ahmed G. Attallah、Reinhard Krause-Rehberg、Christoph Janiak、Hans-Jürgen Holdt

  DOI：10.1039/c7dt00350a

  日期：——

  Microwave heating (MW)-assisted synthesis has been widely applied as an alternative method for the chemical synthesis of organic and inorganic materials. In this work, we report MW-assisted synthesis of three isostructural 3D frameworks with a flexible linker arm of the chelating linker 2-substituted imidazolate-4-amide-5-imidate, named IFP-7-MW (M = Zn, R = OMe), IFP-8-MW (M = Co; R = OMe) and IFP-10-MW

  微波加热（MW）辅助合成已被广泛用作有机和无机材料化学合成的替代方法。在这项工作中，我们报告了MW辅助合成的三个同构3D骨架，该骨架具有螯合接头2-取代的咪唑酸酯-4-酰胺-5-亚氨酸酯的挠性接头臂，命名为IFP-7-MW（M = Zn，R = OMe），IFP-8-MW（M = Co； R = OMe）和IFP-10-MW（M = Co； R = OEt）（IFP =咪唑酯骨架波茨坦）。这些螯合配体是原位产生的通过在MF-和传统的电加热（CE）辅助条件下在DMF中2-取代的4,5-二氰基咪唑部分水解。通过红外光谱和粉末X射线衍射（PXRD）确定这些材料的结构，并确定了在CE条件下合成的材料的身份。MW加热获得的材料显示出CO 2和H 2的许多倍增强与类似的基于CE加热方法的材料相比，其吸收能力更高。为了了解IFP结构的内部孔径和气体吸附的变化，我们进行了正电子an没寿命谱（PALS），表
• Gate effects in a hexagonal zinc-imidazolate-4-amide-5-imidate framework with flexible methoxy substituents and CO2 selectivity
  作者：Suvendu Sekhar Mondal、Asamanjoy Bhunia、Igor A. Baburin、Christian Jäger、Alexandra Kelling、Uwe Schilde、Gotthard Seifert、Christoph Janiak、Hans-Jürgen Holdt

  DOI：10.1039/c3cc42156b

  日期：——

  A new imidazolate-4-amide-5-imidate based MOF, IFP-7, is generated, having flexible methoxy groups, which act as molecular gates for guest molecules. This allows highly selective CO2 sorption over N2 and CH4 gases.

  我们生成了一种新型咪唑-4-酰胺-5-亚胺基 MOF IFP-7，它具有灵活的甲氧基，可作为客体分子的分子门。这样就可以高度选择性地吸附二氧化碳，而不吸附N2和CH4气体。
• Hydrogen-bonded supramolecular metal-imidazolate frameworks: gas sorption, magnetic and UV/Vis spectroscopic properties
  作者：Anas Alrefai、Suvendu Sekhar Mondal、Alexander Wruck、Alexandra Kelling、Uwe Schilde、Philipp Brandt、Christoph Janiak、Sophie Schönfeld、Birgit Weber、Lawrence Rybakowski、Carmen Herrman、Katlen Brennenstuhl、Sascha Eidner、Michael U. Kumke、Karsten Behrens、Christina Günter、Holger Müller、Hans-Jürgen Holdt

  DOI：10.1007/s10847-019-00926-6

  日期：2019.8.15

  reaction parameters for the syntheses of the hydrogen-bonded metal-imidazolate frameworks (HIF) HIF-1 and HIF-2 (featuring 14 Zn and 14 Co atoms, respectively) to increase their yields and crystallinity, we found that HIF-1 is generated in two different frameworks, named as HIF-1a and HIF-1b. HIF-1b is isostructural to HIF-2. We determined the gas sorption and magnetic properties of HIF-2. In comparison

  通过改变氢键金属咪唑骨架 (HIF) HIF-1 和 HIF-2（分别具有 14 个 Zn 和 14 个 Co 原子）的合成反应参数以提高它们的产率和结晶度，我们发现 HIF-1在两个不同的框架中生成，命名为 HIF-1a 和 HIF-1b。HIF-1b 与 HIF-2 具有同构性。我们确定了 HIF-2 的气体吸附和磁性。与 HIF-1a（Brunauer-Emmett-Teller (BET) 表面积为 471 m2 g-1）相比，HIF-2 具有整体非常低的气体吸附吸收能力 [BET(CO2) 表面积 = 85 m2 g-1] . HIF-2 的变温磁化率测量表明在较低温度下钴 (II) 高自旋中心之间的反铁磁交换相互作用。密度泛函理论的理论分析证实了这一发现。