(5aR,5bR,11aS,11bS)-5a,5b,11a,11b-tetrahydrocyclobuta[1,2-b:3,4-b']dichromene-6,12-dione | 1160000-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (5aR,5bR,11aS,11bS)-5a,5b,11a,11b-tetrahydrocyclobuta[1,2-b:3,4-b']dichromene-6,12-dione
• CAS: 1160000-10-1
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: GJYYKBVCTRRXOH-QDUFDSBWSA-N

物化性质

• 沸点：
  512.2±50.0 °C(predicted)
• 密度：
  1.394±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  反应 96.0h， 生成 (5aR,5bR,11aS,11bS)-5a,5b,11a,11b-tetrahydrocyclobuta[1,2-b:3,4-b']dichromene-6,12-dione
  参考文献：
  名称：

  Modulating the reactivity of chromone and its derivatives through encapsulation in a self-assembled phenylethynylene bis-urea host

  摘要：

  This manuscript reports on the modulation of the photoreactivity of a series of chromones, also known as benzo-gamma-pyrones, by absorption into a porous self-assembled host formed from phenylethynylene bis-urea macrocycles. Chromone and four derivatives namely 6-fluorochromone, 6-bromochromone, 7-hydroxy-4-chromone, and 3-cyanochromone are unreactive in the solid-state. Each of these derivatives was loaded into the nanochannels of self-assembled phenylethynylene his-urea macrocycles to form solid host.guest complexes, which were subsequently UV-irradiated at room temperature under argon atmosphere. We observed that chromone and 6-fluorochromone underwent selective [2+2] photo-dimerization reactions to produce anti-HT dimers in high selectivity and conversion. The 6-bromochromone also reacted in high selectivity and conversion to afford an aryl coupling adduct. In each case, the products were extracted, and the crystalline host recovered. In comparison, 7-hydroxy-4-chromone, and 3-cyanochromone were unreactive within the complex. Simple GCMC simulation studies suggest that chromone, 6-fluorochromone, and 6-bromochromone were loaded in orientations that facilitate photoreaction, and correctly predicted that the anti-HT dimer would be favored in the chromone case. In contrast, syn-HH dimers were predicted by GCMC simulations for the halogen containing derivatives but were not observed. The simulations with 7-hydroxy-4-chromone were in agreement with the observed reactivity. We compare these computational and experimental findings and suggest future methods for optimizing simulation parameters. Our goal is to expand the scope and accuracy of the simulations to be able to predict the reactivity of guests encapsulated within columnar nanotubes. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.09.003

文献信息

• Photodimerization of chromone
  作者：Masami Sakamoto、Masayuki Kanehiro、Takashi Mino、Tsutomu Fujita

  DOI：10.1039/b822829a

  日期：——

  Irradiation of the simple chromone (benzo-γ-pyrone) resulted in the formation of two types of dimers, anti-HT (head-to-tail) and trans-fused HTisomers, whose structures were established by X-ray structural analysis.

  辐照单色酮（苯并-γ-吡喃酮）可形成两种二聚体，即反HT（头对尾）和反式融合HT异构体，并通过X射线结构分析确定了它们的结构。