9-bromo<2.2>paracyclophan-9-en-1-one | 109764-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-bromo<2.2>paracyclophan-9-en-1-one
• 英文别名: 10-Brom<2.2>paracyclophan-9-en-1-on
• CAS: 109764-66-1
• 化学式: C₁₆H₁₁BrO
• 分子量: 299.167
• InChiKey: QOJDOHCGNOVWNA-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  9-bromo<2.2>paracyclophan-9-en-1-one 在 2,6-二甲基吡啶 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 9-(n-butyl)-9-<(tert-butyldimethylsilyl)oxy><2.2>paracyclophan-1-ene
  参考文献：
  名称：

  Photophysics of Poly(paracyclophan-1-ene) and Derivatives: Evidence for Intrachain Energy Transfer and Chromophore Aggregation

  摘要：

  The monomer [2.2]paracyclophan-1-ene (2) reacts with the Schrock initiator Mo(NAr)(OC(CF3)(2)Me)(2)-(CHCMe(2)Ph) (1, Ar = 2,6-diisopropylphenyl), via a living and cis-specific ring-opening metathesis polymerization (ROMP) mechanism, to give poly2 in essentially quantitative yield. This polymerization is significantly slower than those observed with monomers built on the norbornene skeleton, The monomers 9-[(tert-butyldimethylsilyl)oxy][2 .2]paracyclophan-1-ene (3) and 9-(n-butyl)-9-[(tert-butyldimethylsilyl)oxy][2.2]paracyclophan-1-ene (4) react similarly, but the resulting polymers are significantly more soluble as a result of the increased saturated content of the polymer chain. Depending on the manner of monomer addition, it is possible to prepare either random or block copolymers (of narrow polydispersity). Poly2, poly3, and poly4 obtained with 1 are stereoregular main-chain polystilbenes with close structural links to poly(p-phenylenevinylene). Poly2 and poly3 in particular have a strong, vibronically defined, red-shifted component in their photoluminescence spectra which depends strongly on the polymer stereochemistry, proximity of chromophores, backbone substitution, ability of the medium to solvate the polymer coils, and length of the stilbene-containing segments. These data suggest that chromophore cooperativity, or aggregation, is responsible for the lower energy fluorescence band. Fluorescence depolarization and lifetime measurements are consistent with significant energy transfer from excited monomeric stilbenes to ''aggregated'' sites. Poly4 is sufficiently substituted that chromophore cooperativity is observed only in the film state and in poor solvents which contract coil dimensions. The oxidative photocyclization of the stilbene components to phenanthrene (poly5) proceeds quantitatively using iodine and a large excess of propylene oxide. This structural change causes a significant decrease in the poly:ner's hydrodynamic volume, and importantly, no evidence of chromophore cooperativity has been observed in poly5.

  DOI：

  10.1021/ja00151a004
• 作为产物：
  描述：

  对二甲苯二聚体 在 potassium tert-butylate 、 溴 作用下， 生成 1,9(10)-dibromo<2.2>paracyclophane-1,9-diene 、 9-bromo<2.2>paracyclophan-9-en-1-one 、 1,10-Dibrom<2.2>paracyclophan-1-en 、 1,9-Dibrom<2.2>paracyclophan-1-en
  参考文献：
  名称：

  Stoebbe, Michael; Reiser, Oliver; Naeder, Reinhard, Chemische Berichte, 1987, vol. 120, p. 1667 - 1674

  摘要：

  DOI：