4-acetyl[2.2]paracyclophane oxime | 741707-36-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4-acetyl[2.2]paracyclophane oxime
• 英文别名: 5-acetyl[2,2]paracyclophane oxime；N-[1-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)ethylidene]hydroxylamine
• CAS: 741707-36-8
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: UVNNRGDNWAZUMD-UHFFFAOYSA-N

物化性质

• 熔点：
  180-183 °C(Solv: ethanol (64-17-5))
• 沸点：
  438.7±34.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-acetyl[2.2]paracyclophane oxime 在 氢氧化钾 、 苄基三甲基氢氧化铵 、 三氯氧磷 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 7.5h， 生成 2-formyl-5-([2,2]-5-paracyclophanyl)-3H-pyrrolizine
  参考文献：
  名称：

  2-（[[2,2] -5-Paracyclophanylyl）pyrrole的合成及某些化学转化

  摘要：

  DOI：

  10.1023/b:cohc.0000027887.37811.27
• 作为产物：
  描述：

  1-三环[8.2.2.24,7]十六-4,6,10,12,13,15-六烯-5-基-乙酮 在 盐酸羟胺 作用下， 以97%的产率得到4-acetyl[2.2]paracyclophane oxime
  参考文献：
  名称：

  Novel BODIPY preparations from sterically hindered pyrroles. Synthesis and photophysical behavior in solution, polystyrene nanoparticles, and solid phase

  摘要：

  Trimesityl-BODIPY (TMB), a new derivative of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene belonging to fluores-cent nanostructures series, was synthesized from the corresponding pyrrole by the Trofimov reaction. This reaction was also employed to obtain 2-[2.2]paracyclophanylpyrrole from 5-acetyl[2.2]-paracyclophane. The spectral properties of TMB have been investigated in dichloromethane, nanolatex (polystyrene) films prepared by rapid solvent evaporation, and microcrystals. Comparative analysis of TMB properties with those of mesityl-BODIPY (MB) was performed. TMB was prepared to minimize pi-pi interactions in order to preserve luminescence in the aggregate state. Both fluorophores were shown to form fluorescing aggregates in the amorphous state (film). Fluorescence spectra (extinction and lifetime) were also studied. In crystal, MB shows a weaker fluorescence, while TMB behaves as a single fluorescing aggregate with a lifetime of 9.5 ns.

  DOI：

  10.1134/s1070363208110467

文献信息

• Palladium-Catalyzed CH Bond Acetoxylation: An Approach to<i>ortho</i>-Substituted Hydroxy[2.2]paracyclophane Derivatives
  作者：Petra Lennartz、Gerhard Raabe、Carsten Bolm

  DOI：10.1002/adsc.201200625

  日期：2012.11.26

  The palladium-catalyzed direct CH bond acetoxylation of [2.2]paracyclophanes has been investigated. Various mono- and disubstituted [2.2]paracyclophanes were subjected to typical Sanford acetoxylation conditions. Oxime ethers, an oxime acetate, a pyridine, and a pyrazole with [2.2]paracyclophane cores underwent direct ortho-acetoxylation in good to excellent yields using 1–5 mol% of palladium(II) acetate

  研究了钯催化的[2.2]对环环烷的直接CH键乙酰氧基化。各种单取代和双取代的[2.2]对环环烷都要经受典型的Sanford乙酰氧基化条件。肟醚，肟酯，吡啶，并用[2.2]对环芳烷核后行直接吡唑邻良好乙酰氧基化，以优异的产率与二乙酸碘苯作为氧化剂组合使用1-5摩尔％的钯（II）乙酸盐。该反应可以在数克范围内进行，并且邻-乙酰氧基化的[2.2]对环环烷适于进一步官能化，从而提供羟基[2.2]对环环烷衍生物和平面手性苯并恶唑。