γ-isopropyloxy-α,β,β',α'-tetrafluoropyridine

• 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: γ-isopropyloxy-α,β,β',α'-tetrafluoropyridine
• 英文别名: 4-isopropyloxy-2,3,5,6-tetrafluoropyridine；2,3,5,6-tetrafluoro-4-isopropoxypyridine；4-(CH3)2CHO-C5F4N；2,3,5,6-tetrafluoro-4-propan-2-yloxypyridine
• 化学式: C₈H₇F₄NO
• 分子量: 209.143
• InChiKey: OJOKSBSNRKYMFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  nonafluoro-2,3,4,5-tetrahydropyridine 在 steel wool 作用下， 以 异丙醇 为溶剂， 生成 γ-isopropyloxy-α,β,β',α'-tetrafluoropyridine
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.5, 4, page 115 - 148

  摘要：

  DOI：

文献信息

• Polynucleotides and Their Components in the Processes of Aromatic Nucleophilic Substitution: I. Chemistry and Dynamics of Nucleotide Arylation with Pentafluoropyridine; Obtaining of Synthons for Molecular Design of Nucleic Acid Analogues
  作者：V. V. Litvak、I. Ya. Mainagashev、O. G. Bukhanets

  DOI：10.1023/b:rubi.0000015773.37915.3b

  日期：2004.1

  the nucleoside secondary hydroxyls. The resulting ethers contain tetrafluoropyridyl moieties, which could be smoothly modified by nucleophilic substitution of fluorine atoms. The ethers are useful intermediate synthons (both isolated and in situ) for molecular design of oligonucleotide analogues. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 1; see also

  五氟吡啶与胸苷，腺苷和尿苷羟基反应，可定量得到相应的核苷二-和三芳基醚。亲核取代反应连续且平行地进行，最慢的步骤是核苷仲羟基的亲核取代。所得的醚包含四氟吡啶基部分，其可以通过氟原子的亲核取代而平滑地改性。醚是用于寡核苷酸类似物的分子设计的有用的中间合成子（分离的和原位的）。该论文的英文版：Russian Journal of Bioorganic Chemistry，2004年，第1卷。30号 1; 另请参见http://www.maik.ru。
• Polyfluoro-heterocyclic compounds. Part XI. Factors controlling the orientation of nucleophilic substitution in octafluoro-3,3′-bipyridyl and related compounds
  作者：R. D. Chambers、D. Lomas、W. K. R. Musgrave

  DOI：10.1039/j39680000625

  日期：——

  alkoxides in the corresponding alcohols to give 4- and 6-substituted compounds, the orientation being dependent both on the nucleophile and the solvent. Methyl-lithium and ammonia in ether lead exclusively to 6-substitution. From these results, and disubstitution with methoxide, it is concluded that the orientation of substitution is affected both by steric requirements of the nucleophile and the polarity

  八氟-3,3'-联吡啶基可以通过Ullmann合成获得，并与相应醇中的醇盐反应生成4-和6-取代的化合物，其取向同时取决于亲核试剂和溶剂。醚中的甲基锂和氨仅导致6取代。从这些结果以及与甲醇的分解作用，可以得出结论，取代的方向受亲核试剂的空间要求和介质极性的影响，这在过渡态的相对电荷离域化方面可能是合理的，并且可能通过试剂与环氮的相互作用。结果表明，醇盐离子的空间要求非常依赖于溶剂。
• Hetarenium salts from pentafluoropyridine. Syntheses, spectroscopic properties, and applications
  作者：Andreas Schmidt、Thorsten Mordhorst、Jan Christoph Namyslo、Werner Telle

  DOI：10.1002/jhet.5570440326

  日期：2007.5

  Reaction of pentafluoropyridine with nucleophilic heteroaromatics such as 4-(dimethylamino)pyridine, 4-(pyrrolidin-1-yl)pyridine, 4-(morpholin-4-yl)pyridine, 4-aminopyridine, and 3,4-diaminopyridine resulted in the formation of 4-hetarenium substituted tetrafluoropyridines. The 4-(dimethylamino)-pyridinium derivative underwent substitution reactions with isopropanolate, isopropanethiolate, and benzylthiolate

  五氟吡啶与亲核杂芳族化合物如4-（二甲基氨基）吡啶，4-（吡咯烷-1-基）吡啶，4-（吗啉-4-基）吡啶，4-氨基吡啶和3,4-二氨基吡啶的反应导致形成4- are取代的四氟吡啶。4-（二甲基氨基）-吡啶衍生物与异丙醇盐，异丙基硫醇盐和苄基硫醇盐进行取代反应，生成F 2，F 3，O 4，F 5，F 6以及O 2，F 3，O 4，F 5，F 6。 -五取代的吡啶及其硫类似物。ñ-丙胺，异丙胺和哌啶在酰胺钠为碱的情况下形成4-氨基-N 2，F 3，F 5，F 6-五取代的吡啶，而吗啉则生成4-氨基-2,6-双-吗啉代-取代的3，5-二氟吡啶。进行19 F，15 N，13 C和1 H nmr光谱分析以阐明取代产物的结构。
• Chemistry and Dynamics of Interaction of Nucleosides with Pentafluoropyridine
  作者：V. V. Litvak、I. Ya. Mainagashev、O. G. Bukhanets

  DOI：10.1080/15257770500230772

  日期：2005.8

  Interaction of pentafluoropyridine with hydroxyl groups of thymidine, uridine, adenosine, and deoxyadenosine at room temperature leads to the formation of aryl ethers of nucleosides with a high yield. Under severe conditions, one more tetrafluoropyridine residue is attached to pyrimidine fragments of T and U, while purine heterocycle in A remains intact. Nucleoside derivatives are formed with a quantitative yield and can be used in situ as intermediates for, as an example, molecular design of arene analogs of nucleic acids. The reaction with thymidine is a successive-parallel process, the limited stage being arylation of the secondary hydroxyl group. The presence of the vicinal hydroxyl group in pentose results in the opposite rate ratio of the formation of primary and secondary tetrafluoropyridyl ethers of adenine and uridine.