4-tert-butyl-2,6-di(1,8-naphthyrid-2-yl)pyridine | 866403-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-tert-butyl-2,6-di(1,8-naphthyrid-2-yl)pyridine
• 英文别名: 2,2’-(4-(tert-butyl)pyridine-2,6-diyl)bis(1,8-naphthyridine)；2,2'-(4-(tert-butyl)pyridine-2,6-diyl)bis(1,8-naphthyridine)；4-tert-butyl-2,6-di-1’,8’-(naphthyrid-2’-yl)-pyridine；2-[4-Tert-butyl-6-(1,8-naphthyridin-2-yl)pyridin-2-yl]-1,8-naphthyridine；2-[4-tert-butyl-6-(1,8-naphthyridin-2-yl)pyridin-2-yl]-1,8-naphthyridine
• CAS: 866403-80-7
• 化学式: C₂₅H₂₁N₅
• 分子量: 391.475
• InChiKey: JFOMKILHVAFGLF-UHFFFAOYSA-N

物化性质

• 沸点：
  596.0±50.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-2,6-di(1,8-naphthyrid-2-yl)pyridine 、 ruthenium(III) chloride trihydrate 生成
  参考文献：
  名称：

  近红外吸收钌 (II) 复合物作为免疫保护光动力疗法 (PDT) 药剂对抗侵袭性黑色素瘤

  摘要：

  过去 20 年来越来越多的证据表明，光动力疗法 (PDT) 是一种主要被称为局部治疗的抗癌方式，它能够引发全身性抗肿瘤免疫反应，从而防止肿瘤复发。对于黑色素瘤等侵袭性癌症，化疗和放疗无效，免疫调节 PDT 作为手术的辅助手段是令人感兴趣的。为了开发用于治疗色素性黑色素瘤的专用光敏剂 (PSs)，九种基于 Ru( II ) 三异配支架 [Ru(NNN)(NN)(L)]Cl n的新型近红外 (NIR) 吸收 PSs ，进行了探索。化合物2、6和9对黑色素瘤细胞表现出高效力，具有可见的 EC50 个值低至 0.292–0.602 μM，PI 高达 156–360。使用近红外光 (733 nm) 获得单微摩尔光毒性，PI 高达 71。这些先导近红外 PS 的共同特征是高单线态氧( 1 O 2 ) 量子产率 (69–93%)，只有当光敏3 IL 态的能量低于通常控制 Ru( II ) 多吡啶基光物理学的最低三重态金属到配体电荷转移

  DOI：

  10.1039/d0sc03875j
• 作为产物：
  描述：

  2-氨基-3-吡啶甲醛 、 4-tert-butyl-2,6-diacetylpyridine 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以87%的产率得到4-tert-butyl-2,6-di(1,8-naphthyrid-2-yl)pyridine
  参考文献：
  名称：

  A New Family of Ru Complexes for Water Oxidation

  摘要：

  Reaction of the bridging ligand 3,6-bis-[6'-(1' ',8' '-naphthyrid-2' '-yl)-pyrid-2'-yl]pyridazine (1) with [Ru(DMSO)4Cl2] in aqueous ethanol followed by excess 4-substituted pyridine (4-R-py) in the presence of triethylamine provides a series of three well-organized dinuclear complexes characterized by 1H NMR, MS, and X-ray. Mononuclear analogues are prepared from 4-tert-butyl-2,6-di(1',8'-naphthyrid-2'-yl)pyridine (5) and characterized in a similar fashion. All six complexes show electronic absorption and redox properties consistent with the electron donor/acceptor ability of the axial 4-R-py ligand. When an acetonitrile solution of the catalyst is added to an aqueous Ce(IV)-CF3SO3H solution (pH = 1.0) at 24 degrees C, oxygen evolution is observed for both mono and dinuclear systems. Turnover numbers range from 50 to 3200 with the best results being found when the axial ligand is 4-methylpyridine (mononuclear TN = 580 and dinuclear TN = 3200).

  DOI：

  10.1021/ja054791m

文献信息

• NIR‐Absorbing Ru ^II Complexes Containing α‐Oligothiophenes for Applications in Photodynamic Therapy
  作者：Liubov M. Lifshits、John A. Roque、Houston D. Cole、Randolph P. Thummel、Colin G. Cameron、Sherri A. McFarland

  DOI：10.1002/cbic.202000419

  日期：2020.12.11

  report the first NIR‐RuII photosensitizers found to be phototoxic to cancer cells, including highly pigmented melanoma cells. They incorporate a bis(1,8‐naphthyridine)‐based ligand, a bidentate thiophene‐based ligand, and a monodentate 4‐picoline ligand. Transient absorption measurements indicate that four thiophenes are required to access the 3ILCT state for eliciting photodynamic therapy effects.

  围绕癌症运行的环：我们报告了第一个被发现对癌细胞（包括高度色素化的黑色素瘤细胞）具有光毒性的 NIR-Ru II光敏剂。它们包含双（1,8-萘啶）基配体、二齿噻吩基配体和单齿4-甲基吡啶配体。瞬时吸收测量表明需要四个噻吩才能进入3 ILCT 状态以引发光动力治疗效果。
• A Ru(II) Bis-terpyridine-like Complex that Catalyzes Water Oxidation: The Influence of Steric Strain
  作者：Nattawut Kaveevivitchai、Lars Kohler、Ruifa Zong、Maya El Ojaimi、Nirja Mehta、Randolph P. Thummel

  DOI：10.1021/ic4016383

  日期：2013.9.16

  The complexation of 2,9-dicarboxy-1,10-phenanthroline (DPA) with [Ru(tpy)Cl-3] (tpy = 2,2';6,2 ''-terpyridine) provides a six-coordinate species in which one carboxyl group of DPA is not bound to the Ru(II) center. A more soluble tri-t-butyl tpy analogue is also prepared. Upon oxidation, neither species shows evidence for intramolecular trapping of a seven-coordinate intermediate. The role of the tpy ligand is revealed by the preparation of [Ru(tpy)(phenq)](2+) (phenq = 2-(quinol-8'-yl)-1,10-phenanthroline) that behaves as an active water oxidation catalyst (TON = 334). This activity is explained by the expanded coordination geometry of the phenq ligand that can form a six-membered chelate ring that better accommodates the linear arrangement of axial ligands required for optimal pentagonal bipyramid geometry. When a 1,8-naphthyidine ring is substituted for each of the two peripheral pyridine rings on tpy, increased crowding in the vicinity of the metal center impedes acquisition of the prerequisite reaction geometry.