4-(Tetrahydro-2-pyranoxy)-2,6-pyridinedimethyl Ditosylate | 111042-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(Tetrahydro-2-pyranoxy)-2,6-pyridinedimethyl Ditosylate
• 英文别名: [6-[(4-Methylphenyl)sulfonyloxymethyl]-4-(oxan-2-yloxy)pyridin-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 111042-48-9
• 化学式: C₂₆H₂₉NO₈S₂
• 分子量: 547.65
• InChiKey: IPXUEZSPRWSQGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(Tetrahydro-2-pyranoxy)-2,6-pyridinedimethyl Ditosylate 在 氢化钾 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 叔丁醇 为溶剂， 反应 73.67h， 生成 19-n-octoxy-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene
  参考文献：
  名称：

  Bradshaw, Jerald S.; Nakatsuji, Yohji; Huszthy, Peter, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 353 - 360

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氧代-1,4-二氢-2,6-吡啶二甲酸 在 sodium tetrahydroborate 、 氯化亚砜 、 4-甲基苯磺酸吡啶 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 43.0h， 生成 4-(Tetrahydro-2-pyranoxy)-2,6-pyridinedimethyl Ditosylate
  参考文献：
  名称：

  吲哚包含在针对神经退行性变分子特征的多战术金属结合 Tetra-Aza 大环设计中的影响

  摘要：

  许多小分子对抗氧化应激的能力已被研究，氧化应激是导致阿尔茨海默病等神经退行性疾病的关键因素。尽管做出了这些努力，但这些化合物的药理学特性和构效关系仍未得到充分了解，但它们在评估药物分子的治疗潜力方面至关重要。修饰的 tetra-aza 大环通过各种机制表现出强大的抗氧化活性;然而，其有限的渗透性为高级配方研究带来了挑战。为了提高渗透性，同时保持母体分子的有益反应性，探索了两种涉及吲哚官能团的合成修饰，并与单独使用甲基的修饰进行了比较。开发了新的合成策略来生产含吲哚的分子，这些分子通过 1D/2D NMR 技术进行表征。测定等电点、金属结合和自由基清除活性，以验证母体分子的反应性是否被保留。研究的所有分子的通透性均得到改善。通过测量处理后的 ROS 水平以及 HO-1 和 Nrf2 的 mRNA 水平，证明了在细胞模型中含有吲哚的分子通过激活 Nrf2 途径来防止氧化应激。相比之下，在 O 或

  DOI：

  10.1021/acschemneuro.4c00530

文献信息

• Facile Access to the 12-Membered Macrocyclic Ligand PCTA and Its Derivatives with Carboxylate, Amide, and Phosphinate Ligating Functionalities
  作者：Morgane Enel、Nadine Leygue、Nathalie Saffon、Chantal Galaup、Claude Picard

  DOI：10.1002/ejoc.201800066

  日期：2018.4.23

  convenient and efficient alternative to the classical Richman–Atkins methodology for obtaining PCTA and new derivatives is reported. The key macrocyclization step occurs in good yields as a result of a sodium template effect. The potentiality of lanthanide(III) complexes derived from these new PCTA ligands to act as paramagnetic contrastophores or luminophores is reported.

  据报道，它是传统的Richman-Atkins方法获得PCTA和新衍生物的一种便捷有效的替代方法。由于钠模板效应，关键的大环化步骤以高收率发生。据报道，衍生自这些新的PCTA配体的镧系元素（III）可能用作顺磁性造影剂或发光体。
• A new Efficient Method for the Preparation of 2,6-Pyridinedihiethyl Ditosylates from Dimethyl 2,60-Pyridinedicarboxylates
  作者：György Howáth、Cristian Rusa、Zoltán Köntös、János Gerencsér、Péter Huszthy

  DOI：10.1080/00397919908086011

  日期：1999.11

  report here an efficient method for the preparation of 2,6-pyridinedimethyl ditosylate and four of its 4-substituted derivatives, two of them have not been reported in the literature. We also describe here a modification of the reported synthesis for chelidonic and chelidamic acids with improved yields and higher purity.

  摘要 我们在此报告了一种制备 2,6-吡啶二甲基二甲苯磺酸酯及其四种 4-取代衍生物的有效方法，其中两种尚未在文献中报道。我们还在这里描述了对已报道的螯合酸和螯合酸合成的改进，具有更高的产率和更高的纯度。
• Synthesis of New Pyridinoazacrown Ethers Containing Aromatic and Heteroaromatic Proton Ionizable Substituents
  作者：Andrei V. Bordunov、Paul C. Hellier、Jerald S. Bradshaw、N. Kent Dalley、Xiaolan Kou、Xian Xin Zhang、Reed M. Izatt

  DOI：10.1021/jo00124a022

  日期：1995.9

  Methods for the synthesis of pyridinocrowns functionalized with various proton ionizable groups have been elaborated. Sixteen new ligands containing pyridine rings as part of the macrocycle or as a side arm have been prepared. Different interactive abilities of the OH and NH functions of 3,9-dioxa-6-azaundecane-1,11-diol (3) in strong base allowed the synthesis of pyridinoazacrowns 1 and 2 by cyclization with 2,6-bis((tosyloxy)methyl)pyridine (4) and THP-protected 4-hydroxy-2,6-bis(tosyloxy)methyl)pyridine (5). Pyridinoazacrown 1 was functionalized with different proton ionizable side arms by treatment first with formaldehyde in methanol to form the N-methoxymethyl derivative 6 and then treating 6 with 5-chloro-8-hydroxyquinoline or the appropriate substituted phenol. Pyridinoaza-18-crown-6 ligands containing p-methylphenol (7), p-methoxyphenol (8), p-chlorophenol (9),p-fluorophenol (10),p-cyanophenol (11), 2-formyl-4-bromophenol (12), or 5-chloro-8-hydroxyquinoline (13) groups were prepared by this process. Pyridinoazacrowns 1 and 2 were alkylated with 2-hydroxy-5-nitrobenzyl chloride or 5-chloro-8-methoxy-2-(bromomethyl)quinol followed by removal of the protecting groups to form p-nitrophenol- and 5-chloro-8-hydroxy-2-quinolinyl-substituted ligands (16, 18, and 21). Macrocycles 22 and 23 containing proton ionizable triazole and phenol functions inside the macrocyclic cavity and a pyridine side arm were prepared by cyclization of the appropriate dihalide with 6-(2'-pyridylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol followed by cleavage of the THP or methoxy protecting groups. Preliminary complexation data show that the phenol-substituted pyridinoaza-18-crown-6 ligands form strong complexes with various metal cations and exhibit high selectivity toward Ag+. Macrocycle 16 containing a p-nitrophenol substituent formed a complex with benzylamine. The crystal structures for 16 and its benzylamine complex are also given here.
• Bradshaw, Jerald S.; Krakowiak, Krzysztof E.; Huszthy, Peter, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 3, p. 773 - 775
  作者：Bradshaw, Jerald S.、Krakowiak, Krzysztof E.、Huszthy, Peter、Izatt, R. M.

  DOI：——

  日期：——
• Chromatographic enantioseparation of racemic α-(1-naphthyl)ethylammonium perchlorate by a Merrifield resin-bound enantiomerically pure chiral dimethylpyridino-18-crown-6 ligand
  作者：György Horváth、Péter Huszthy

  DOI：10.1016/s0957-4166(99)00515-7

  日期：1999.12

  Three novel chiral pyridino-18-crown-6 ligands (S,S)-1, (S,S)-2 and (S,S)-3 were prepared and (S,S)-1 was attached to a Merrifield resin. The resulting adsorbent (S,S)-5 was used as a chiral stationary phase in the chromatographic enantioseparation of racemic alpha-(1 -naphthyl)ethylammonium perchlorate. Also, a new chiral pyridono-18-crown-6 ligand (S,S)-6, used for the synthesis of (S,S)-1 and (S,S)-2, was prepared in two different ways. (C) 1999 Elsevier Science Ltd. All rights reserved.