1,3-dimesityl-4,5-naphthquino-imidazolylidene | 922519-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-dimesityl-4,5-naphthquino-imidazolylidene
• 英文别名: 1,3-dimesityl-4,5-naphthoquino-imidazolylidene；1,3-bis(2,4,6-trimethylphenyl)-2H-benzo[f]benzimidazol-3-ium-2-ide-4,9-dione
• CAS: 922519-61-7
• 化学式: C₂₉H₂₆N₂O₂
• 分子量: 434.538
• InChiKey: JLEMACLQNFGEBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimesityl-4,5-naphthquino-imidazolylidene 在 sodium 作用下， 生成
  参考文献：
  名称：

  Dynamic Tuning of the Bandgap of CdSe Quantum Dots through Redox-Active Exciton-Delocalizing N-Heterocyclic Carbene Ligands

  摘要：

  DOI：

  10.1021/jacs.1c12842
• 作为产物：
  描述：

  N,N'-bis(2,4,6-trimethylphenyl)formamidine 在 potassium tert-butylate 、 sodium hydride 、 sodium sulfate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 96.0h， 生成 1,3-dimesityl-4,5-naphthquino-imidazolylidene
  参考文献：
  名称：

  Quinone-Annulated N-Heterocyclic Carbene−Transition-Metal Complexes:  Observation of π-Backbonding Using FT-IR Spectroscopy and Cyclic Voltammetry

  摘要：

  A new N-heterocyclic carbene architecture comprising a 1,4-naphthoquinone annulated to 1,3-dimesitylimidazolylidene (NpQ-NHC) was synthesized in two high yielding steps from commercially available starting materials. The free NpQ-NHC was characterized (solution and solid-state) and was used to synthesize various Rh and Ag complexes that ranged in pi-electron density. Enabled by the quinone moiety, the pi-systems of these complexes were analyzed using infrared spectroscopy and cyclic voltammetry. In contrast to previous reports, pi-backbonding was found to be non-negligible and was directly influenced by the metal's electronic character.

  DOI：

  10.1021/ja067475w

文献信息

• A Ring‐Opening Metathesis Polymerization Catalyst That Exhibits Redox‐Switchable Monomer Selectivities
  作者：Dominika N. Lastovickova、Huiling Shao、Gang Lu、Peng Liu、Christopher W. Bielawski

  DOI：10.1002/chem.201605738

  日期：2017.5.2

  A ring‐opening metathesis polymerization catalyst supported by a redox‐active N‐heterocyclic carbene was synthesized and found to undergo reversible reduction. In its neutral form, the catalyst polymerized 1,5‐cis,cis‐cyclooctadiene at a higher rate than that of a norbornene derivative; however, upon reduction, the selectivity was found to reverse. Utilizing this oxidation state dependent selectivity

  合成了具有氧化还原活性的N-杂环卡宾负载的开环复分解聚合催化剂，发现该还原催化剂可逆还原。在中性形式下，该催化剂以比降冰片烯衍生物更高的速率聚合1,5-顺式，顺式-环辛二烯。然而，还原后，发现选择性相反。利用这种依赖于氧化态的选择性，通过在一系列聚合反应过程中对催化剂进行氧化还原转换，可制得一系列具有可控组成，微观结构和物理性能的共聚物。
• Synthesis, Crystal Structure Determination and Electrochemistry of Homoleptic Pd(0) Complexes Supported by Normal and Abnormal N-Heterocyclic Carbene Ligands
  作者：Nurul Amin SK、Bibaswan Sen、Sk Jahir Abbas、Sk Imran Ali

  DOI：10.1007/s10870-022-00962-0

  日期：——

  of the palladium centre from Pd(0) to Pd(I) and then Pd(II). Graphical Abstract Abnormal carbene complex of Pd(L1)2, where L1 = 1,3-Bis(2,6-diisopropylphenyl)-2,4-diphenylimidazole and normal carbene complex of Pd(L2)2, where L2 = 1,3-dimesityl-4,9-dioxonaphtho-2,3-diimidazole were prepared from a Pd(0) precursor of Pd(COD)(CH2TMS)2. The crystal structures were determined by single crystal X-ray diffraction

  Pd(L1) 2的异常卡宾络合物，其中 L1 = 1,3-双(2,6-二异丙基苯基)-2,4-二苯基咪唑和 Pd(L2) 2的正常卡宾络合物，其中 L2 = 1,3-二苯甲基-4,9-dioxonaphtho-2,3-diimidazole 由 Pd(0) 前体 Pd(COD)(CH 2 TMS) 2制备。两种配合物均在三斜空间群P -1 中结晶，Pd(L1) 2和 Pd(L2) 2的晶胞参数为a  = 12.0477 Å, b  = 17.5269 Å, c  = 18.9786 Å, α  = 114.4855°, β  = 92.5295°，γ  = 107.9472°，a  = 11.5007 Å，b  = 15.2316 Å，c  = 17.9007 Å，α  = 67.061°，β  = 72.143°，γ  = 72.183°。在这两种情况下，N-杂环配体都向钯方向扭曲。此外，晶体结构表明钯原子分别与两个
• NQNHC Ligand-Enabled Cu(I)-Catalyzed Double Hydroamination: A Regio- and Chemoselective Bicyclization of o-Amino 1,6-Diyne
  作者：Shyam Kumar Banjare、Saista Afreen、Kumar Gaurav、Amiya Kumar Sahoo、Bhagyashree Das、Subhra Jyoti Panda、Chandra Shekhar Purohit、Adinarayana Doddi、Ponneri C. Ravikumar

  DOI：10.1021/acs.joc.4c00199

  日期：2024.7.5

  method for the intramolecular double hydroamination of aniline by employing o-amino 1,6-diyne as a potential starting material. This protocol enables easy access to bioactive motif 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole through an intramolecular cascade bicyclization and concomitant isomerization pathway in one pot. This transformation has been effectively achieved by utilizing a stereoelectronically

  在这项工作中，我们采用邻氨基1,6-二炔作为潜在的起始原料，开发了一种有效的苯胺分子内双氢胺化方法。该方案可以在一锅中通过分子内级联双环化和伴随的异构化途径轻松获得生物活性基序 3,4-二氢-1 H -[1,4]恶嗪基[4,3- a ]吲哚。通过利用立体电子调谐、接受 π 的 NHC 支持的铜 (I) 系统，可以有效地实现这种转变。在配体优化试验中，萘醌环化的N-杂环卡宾，Nq(IDipp)[1,3-双(2,6-二异丙基苯基)-4,5-萘醌-咪唑基]负载的Nq型铜(I)配合物使用各种光谱技术合成并充分表征了 (IDipp)CuX（X = Cl 或 I）。对于这种转换，NHC 在提供金属中心周围的最佳电子密度方面发挥着至关重要的作用。它是一种高度区域和化学选择性转化，具有高原子经济性，并使用廉价、环境友好的铜基催化剂。此外，基于实验观察和文献支持，提出了一种合理的机制。
• Synthesis and Study of Redox-Active Acyclic Triazenes: Toward Electrochromic Applications
  作者：Robert J. Ono、Yasuo Suzuki、Dimitri M. Khramov、Mitsuru Ueda、Jonathan L. Sessler、Christopher W. Bielawski

  DOI：10.1021/jo200139f

  日期：2011.5.6

  Coupling of various 4-substituted phenyl azides with two distinct quinone-containing N-heterocyclic carbenes (NHCs) afforded the respective mono- and ditopic 1,3-disubstituted acyclic triazenes in moderate to excellent yields (38-92%). Depending on their pendant substituents (derived from the azides), the acyclic triazenes exhibited intense absorptions in the visible spectrum (359-428 nm), which were bathochromically shifted by up to Delta lambda = 68 nm upon reduction of the quinone moiety on the component derived from the NHC. Cyclic voltammetry confirmed that the aforementioned redox processes were reversible, and a related set of UV-vis spectroelectrochemical experiments revealed that bulk electrolysis may also be used to switch reversibly the colors exhibited by these triazenes.