6,6'-diacetoxy-2,2'-bipyridine | 102451-14-9

• 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: 6,6'-diacetoxy-2,2'-bipyridine
• 英文别名: 6,6'-Diacetoxy-[2,2']bipyridyl；[6-(6-Acetyloxypyridin-2-yl)pyridin-2-yl] acetate
• CAS: 102451-14-9
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: WQLZAIYKIJKKTN-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C (decomp)
• 沸点：
  449.0±45.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,6'-diacetoxy-2,2'-bipyridine 在 盐酸 作用下， 生成 6,6’-二羟基-2,2’-联吡啶
  参考文献：
  名称：

  Murase, Nippon Kagaku Zasshi, 1956, vol. 77, p. 682,685

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-联吡啶 在 双氧水 、 溶剂黄146 作用下， 生成 6,6'-diacetoxy-2,2'-bipyridine
  参考文献：
  名称：

  Murase, Nippon Kagaku Zasshi, 1956, vol. 77, p. 682,685

  摘要：

  DOI：

文献信息

• Activation of a CH bond in polypyridine systems by acetyl hypofluorite made from F2
  作者：Julia Gatenyo、Youlia Hagooly、Inna Vints、Shlomo Rozen

  DOI：10.1039/c2ob06799d

  日期：——

  Activation of the relatively inactive polypyridine backbone with strong electrophilic fluorine, originating from acetyl hypofluorite (AcOF) enables attack of the acetoxy moiety at the α position to the heteroatom. Derivatives of bipyridine, phenanthroline and terpyridine systems have been acetoxylated or oxygenated within a few minutes usually in very good yields.

  相对惰性的聚吡啶骨架被强亲电氟激活，该氟源于 乙酰基次萤石（AcOF）能够使α位的乙酰氧基部分攻击杂原子。的导数联吡啶， 菲咯啉 和 特吡啶 通常在几分钟内就可以对系统进行乙酰氧基化或氧化，收率非常好。
• Synthesis, Properties, and Reactivity of <i>N,N</i>‘-Difluorobipyridinium and Related Salts and Their Applications as Reactive and Easy-To-Handle Electrophilic Fluorinating Agents with High Effective Fluorine Content¹
  作者：Teruo Umemoto、Masayuki Nagayoshi、Kenji Adachi、Ginjiro Tomizawa

  DOI：10.1021/jo972338q

  日期：1998.5.1

  N,N'-Difluoro-2,2'-, -2,4'-, -3,3'-, -4,4'-bipyridinium and substituted N,N'-difluoro-2,2'-bipyridinium bis(triflates), bis(tetrafluoroborates), bis(hexafluorophosphates), and bis(hexafluoroantimonates) 1-9 were synthesized in high yields by the direct fluorination of a mixture of a bipyridyl and a Lewis acid, a Bronsted acid, or the alkali metal salt of an acid. The higher homologues, trimer 10 and polymer II, were also synthesized. Unsubstituted or electron-donating group-substituted N,N'-difluorobipyridinium salts are stable nonhygroscopic crystals, while the electron-withdrawing group-substituted N,N'-diflurobipyridinium salts 3, 5, and 6 are moisture-sensitive crystals. Hydrolysis of Ib in boiling water gave 3,3'-dihydroxy-2,2'-bipyridyl. The reactivity determination indicated that the fluorinating capability decreased in the order 2,2'- much greater than 2,4' > 3,3'- approximate to 4,4'-isomer much greater than N-fluoropyridinium salt and that the two N-F moieties in a molecule mere effective for fluorination. This fluorination occurred in a step-by-step manner, and the reactivity difference between the first and second fluorinations was very small. N,N'-Difluoro-2,2'-bipyridinium bis(tetrafluoroborate) (Ib) is thus shown to be a highly reactive and easy-to-handle electrophilic fluorinating agent with the high effective fluorine content (103.3 g/kg) for preparing many fluoro organic compounds.